Patel v. Martin , 481 Mass. 29 ( 2018 )


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    SJC-12500
    JAY PATEL & another1   vs.   LEO MARTIN & others.2
    Norfolk.       September 6, 2018. - November 28, 2018.
    Present:    Gants, C.J., Lenk, Gaziano, Lowy, Budd, Cypher,
    & Kafker, JJ.
    Practice, Civil, Discovery, Interlocutory appeal. Attorney at
    Law, Attorney-client relationship. Privileged
    Communication.
    Civil action commenced in the Superior Court Department on
    December 23, 2015.
    A motion for a protective order was heard by Jeffrey A.
    Locke, J.
    The Supreme Judicial Court on its own initiative
    transferred the case from the Appeals Court.
    Peter S. Brooks (Gregory M. Boucher also present) for the
    defendants.
    David V. Lawler for the plaintiffs.
    1   Dipika, Inc.
    2  Seymour H. Marcus, also known as Sy H. Marcus; and Ellen
    Rea Marcus, as trustee of the Grossman Munroe Trust. Leo Martin
    and Seymour Marcus are alleged to have acted on behalf of the
    Grossman Munroe Trust, but only Ellen Rea Marcus was a trustee.
    2
    GANTS, C.J.     The primary issue on appeal is whether a party
    in a civil case has the right to an immediate appeal from a
    discovery order under the doctrine of present execution.       The
    defendants here argue that, after the motion judge ordered the
    disclosure of communications that they contend are protected
    from disclosure by the attorney-client privilege, they will be
    irremediably harmed if they cannot immediately appeal from that
    order.   We conclude that a party has no such right of
    interlocutory appeal.    In so holding, we note that a party
    nevertheless retains two other avenues to seek immediate
    appellate review of an interlocutory order:    by requesting the
    trial court judge to report the decision to the Appeals Court
    under Mass. R. Civ. P. 64 (a), as amended, 
    423 Mass. 1403
    (1996); or by petitioning for redress from a single justice of
    the Appeals Court under G. L. c. 231, § 118, first par.
    Although the appeal is not properly before us under the
    doctrine of present execution, we exercise our discretion under
    our superintendence authority to reach the merits and conclude
    that we must remand the matter to the motion judge for further
    factual findings.
    Background.     We summarize the facts as alleged in the
    complaint and that are undisputed in the record.    In September
    2012, Ellen Rea Marcus, as trustee of the Grossman Munroe Trust
    3
    (trustee), executed a purchase and sale agreement with the
    Masonic Temple Association of Quincy, Inc. (Masons), for the
    purchase of the Masonic Temple in Quincy (property).     Pursuant
    to a rider to the purchase and sale agreement, the agreement
    could not be assigned by the trustee without the prior written
    consent of the Masons.   In a separate agreement executed in
    April 2013, the trustee assigned the rights to the property
    under the purchase and sale agreement to Jay Patel in return for
    $100,000; Patel intended to develop a hotel on the property.        On
    September 30, 2013, before the sale of the property closed, a
    fire caused severe damage to the property.   Shortly thereafter,
    the Masons claimed that they had never consented to the
    assignment, refused to recognize it, and received over $6
    million from an insurance claim arising from the fire.    In
    December 2015, Patel and his "hotel-operating company," Dipika,
    Inc. (collectively, developer plaintiffs), brought a civil
    action in the Superior Court against the trustee, Seymour H.
    Marcus, and Leo Martin (collectively, trust defendants),
    claiming that they suffered economic damages from the trustee's
    failure to obtain the required consent for the assignment of the
    property.
    During the course of discovery, the developer plaintiffs
    noticed the deposition of David Levin, the attorney who
    represented the Masons with respect to the sale of the property
    4
    and who had also routinely represented the trust defendants on
    real estate legal matters for over twenty years.   The trust
    defendants moved for a protective order to bar Levin from
    disclosing his confidential attorney-client communications with
    them, claiming that Levin represented them as well as the Masons
    in the real estate transaction concerning the property, even
    though Levin took the position that he had represented only the
    Masons.
    After an evidentiary hearing, the motion judge found that
    there was an attorney-client relationship between Levin and the
    trust defendants after the fire regarding insurance claims and
    third-party claims arising from the fire, but that, with respect
    to the purchase and sale of the property, Levin represented the
    Masons, not the trust defendants.   He therefore ruled that
    communications between Levin and the trust defendants before the
    fire were not protected by the attorney-client privilege.
    The trust defendants filed a notice of appeal in the
    Superior Court seeking review by an Appeals Court panel under
    the doctrine of present execution and, "in an abundance of
    caution," also brought a petition in the Appeals Court pursuant
    to G. L. c. 231, § 118, first par., seeking interlocutory relief
    from a single justice of the Appeals Court.   The single justice
    stayed action on the § 118 petition until a panel of the Appeals
    Court decided whether it had jurisdiction of the appeal under
    5
    the doctrine of present execution to resolve the discovery
    dispute arising from the claim of attorney-client privilege.       We
    transferred the appeal to this court on our own motion.
    Discussion.     1.   Appellate review of interlocutory orders.
    When a final judgment enters in a civil case in the Superior
    Court under Mass. R. Civ. P. 54, as amended, 
    382 Mass. 829
    (1981), a party aggrieved has the right to appeal from the
    judgment to a panel of the Appeals Court.    See G. L. c. 231,
    § 113.    As part of that appeal, a party may claim that a judge
    erred in the entry of various types of interlocutory orders that
    were issued during the course of the civil case.    If a party
    wishes to seek appellate review of an interlocutory discovery
    order before the entry of final judgment, however, the party
    generally has only two alternatives.    First, the party may ask
    the judge under Mass. R. Civ. P. 64 (a) to report the
    interlocutory finding or order to the Appeals Court, and the
    judge may do so where he or she concludes that the finding or
    order "so affects the merits of the controversy that the matter
    ought to be determined by the [A]ppeals [C]ourt before any
    further proceedings in the trial court."    Mass. R. Civ. P.
    64 (a).   Second, the party has the right to petition for relief
    under G. L. c. 231, § 118, first par., from a single justice of
    the Appeals Court, who may, in his or her discretion, grant the
    relief.   The single justice also has the authority to transfer
    6
    the petition to a panel of the Appeals Court, where it will be
    treated as a full interlocutory appeal.   See McMenimen v.
    Passatempo, 
    452 Mass. 178
    , 187 (2008), citing CUNA Mut. Ins.
    Soc'y v. Attorney Gen., 
    380 Mass. 539
    , 540 (1980).   But a party
    has no right under § 118, first par., to bring the petition
    directly to a panel or to seek review of the single justice's
    ruling by the panel.    See McMenimen, supra at 189-190; Corbett
    v. Kargman, 
    369 Mass. 971
    , 971-972 (1976).
    However, in narrowly limited circumstances, where "an
    interlocutory order will interfere with rights in a way that
    cannot be remedied on appeal" from a final judgment, and where
    the order is "collateral to the underlying dispute in the case"
    and therefore will not be decided at trial, a party may obtain
    full appellate review of an interlocutory order under our
    doctrine of present execution.   Maddocks v. Ricker, 
    403 Mass. 592
    , 596, 598 (1988).   See Marcus v. Newton, 
    462 Mass. 148
    , 151-
    152 (2012); Borman v. Borman, 
    378 Mass. 775
    , 779-780 (1979).3
    The doctrine is intended to be invoked narrowly to avoid
    3 The phrase "doctrine of present execution" appears to
    derive from Vincent v. Plecker, 
    319 Mass. 560
    , 564 n.2 (1946),
    where this court, in deciding whether an order was appealable as
    a "final decree," noted, "Though part of a single controversy
    remains undetermined, if the decree is to be executed presently,
    so that appeal would be futile unless the decree could be
    vacated by the prompt entry of an appeal in the full court, the
    decree is a final one." We first used the phrase "doctrine of
    present execution" in Borman v. Borman, 
    378 Mass. 775
    , 780
    (1979).
    7
    piecemeal appeals from interlocutory decisions that will delay
    the resolution of the trial court case, increase the over-all
    cost of the litigation, and burden our appellate courts.     See
    Borman, supra at 779.   See also Firestone Tire & Rubber Co. v.
    Risjord, 
    449 U.S. 368
    , 374 (1981).
    Our doctrine of present execution is similar to the Federal
    "collateral order doctrine," which permits full appellate review
    of a small class of collateral interlocutory decisions "that are
    conclusive, that resolve important questions separate from the
    merits, and that are effectively unreviewable on appeal from the
    final judgment in the underlying action."     Mohawk Indus., Inc.
    v. Carpenter, 
    558 U.S. 100
    , 106 (2009), quoting Swint v.
    Chambers County Comm'n, 
    514 U.S. 35
    , 42 (1995).    But, as we note
    later, the application of the Federal collateral order doctrine
    has at times varied from our application of the doctrine of
    present execution.   See note 4, infra.
    In civil cases, we have granted "the right to an immediate
    appeal under the doctrine of present execution where protection
    from the burden of litigation and trial is precisely the right
    to which [a party] asserts an entitlement."    Estate of Moulton
    v. Puopolo, 
    467 Mass. 478
    , 485 (2014).    Thus, for example, we
    allow immediate appeals from an order denying a motion to
    dismiss by a government official who claims absolute or
    qualified immunity, because the purpose of such immunity is to
    8
    protect public officials from the burden of litigation itself.
    Duarte v. Healy, 
    405 Mass. 43
    , 44 n.2 (1989).   If the motion to
    dismiss were denied in error, the official would have to defend
    the litigation, which is precisely what the immunity is designed
    to prevent; even if the erroneous order were ultimately reversed
    after trial, the right to immunity from suit would still have
    been "lost forever."   Brum v. Dartmouth, 
    428 Mass. 684
    , 688
    (1999).   Similarly, the doctrine has been applied to allow an
    immediate appeal from the denial of a motion to dismiss under
    the "anti-SLAPP" statute, G. L. c. 231, § 59H, which was enacted
    to protect those exercising their rights of petition and speech
    from lawsuits intended to chill their exercise of those rights
    by the threat of costly and time-consuming litigation.   See
    Blanchard v. Steward Carney Hosp., Inc., 
    477 Mass. 141
    , 157-158
    (2017); Duracraft Corp. v. Holmes Prods. Corp., 
    427 Mass. 156
    ,
    161 (1998).   The interests of defendants under the anti-SLAPP
    statute cannot be adequately vindicated on appeal from a final
    judgment, because they will already have suffered the burdens of
    litigation arising from their exercise of protected rights.     See
    Fabre v. Walton, 
    436 Mass. 517
    , 521 (2002).
    We have also allowed immediate appeal from an interlocutory
    order disqualifying a party's counsel in a civil case under the
    doctrine of present execution.   We concluded that an order
    depriving a party of his or her choice of counsel, if error,
    9
    cannot realistically be remedied on appeal from a final
    judgment.   
    Maddocks, 403 Mass. at 600
    .    Even if the appellate
    court were to determine that the judge erred in disqualifying
    the attorney, "[i]n practice, . . . it is unlikely that an
    appellate court would reverse a judgment and require a new trial
    in the absence of a demonstration, almost impossible to make,
    that any erroneous disqualification order significantly
    prejudiced the rights of the client."     Id.4
    We have not, however, generally allowed interlocutory
    discovery orders to be immediately appealable under the doctrine
    of present execution.   See Cronin v. Strayer, 
    392 Mass. 525
    , 527
    (1984).   The United States Supreme Court has also not generally
    allowed such appeals under the collateral order doctrine.
    Mohawk Indus., 
    Inc., 558 U.S. at 108
    , quoting Firestone Tire &
    Rubber 
    Co., 449 U.S. at 377
    ("we have generally denied review of
    pretrial discovery orders").
    4  The United States Supreme Court has concluded under its
    collateral order doctrine that an order disqualifying counsel in
    a civil case is not immediately appealable. Richardson-Merrell,
    Inc. v. Koller, 
    472 U.S. 424
    , 440 (1985). In response to the
    argument that a disqualification order will effectively be
    unreviewable on appeal from a final judgment because of the
    difficulty in showing that the party suffered prejudice, the
    Court declared that "the difficulties in proving prejudice . . .
    go more to the issue of the showing required to reverse a final
    judgment than to whether a disqualification order should be
    subject to immediate appeal." 
    Id. at 438.
    "Absent a
    requirement of prejudice, the propriety of the trial court's
    disqualification order can be reviewed as effectively on appeal
    of a final judgment as on an interlocutory appeal." 
    Id. 10 The
    trust defendants contend that the judge's partial
    denial of their motion for a protective order regarding their
    communications with Levin deprives them of their right to
    protect privileged attorney-client communications from
    disclosure to third parties, and that this right cannot be
    adequately vindicated on appeal after final judgment because the
    confidentiality of those privileged communications, once
    disclosed, cannot be restored.   They also contend that the
    subject of the interlocutory appeal -- the existence of an
    attorney-client relationship regarding the property transaction
    between Levin and the trust defendants before the fire -- is
    collateral to the merits of the controversy, which concerns the
    assignment of the purchase and sale agreement to Patel.
    In response, the developer plaintiffs argue that a partial
    denial of a motion for protective order is ultimately a
    discovery order, and that litigation should not generally be
    interrupted by allowing piecemeal appeals from such orders.
    They contend that the trust defendants may challenge the order
    on appeal after final judgment and, if the order is determined
    to be error, they can seek a remedy of a new trial where the
    attorney-client communications that were disclosed, and all
    information derived from those disclosures, are excluded from
    evidence.
    11
    The trust defendants make fair points, but the developer
    plaintiffs have the better argument.    The trust defendants are
    correct that the existence of an attorney-client relationship
    between Levin and the trust defendants regarding the sale of the
    property is an issue that is collateral to any issue that will
    be decided at trial.    They are also correct about the importance
    of protecting the confidentiality of privileged attorney-client
    communications in order to encourage "full and frank
    communication between attorneys and their clients."    Upjohn Co.
    v. United States, 
    449 U.S. 383
    , 389 (1981).    And we recognize
    that, if those communications are indeed privileged and are
    disclosed in discovery, a successful postjudgment appeal cannot
    change the fact that communications that the trust defendants
    intended to be confidential will have been disclosed to the
    developer plaintiffs.
    But we agree with the developer plaintiffs that, although a
    successful postjudgment appeal cannot entirely eliminate the
    harm that arises from an order allowing third parties to learn
    the content of privileged communications, the trust defendants
    do have a viable postjudgment remedy.   Unlike an order
    disqualifying a party's counsel, the consequences of an adverse
    discovery order can be ascertained, the prejudice identified,
    and the error remedied by barring the use of any evidence
    derived from the protected communications at a new trial or
    12
    other subsequent proceeding.   See 
    Borman, 378 Mass. at 782
    ("review [of order to testify at depositions] after a definitive
    determination of rights and liabilities would not be futile").
    See also Mohawk Indus., 
    Inc., 558 U.S. at 109
    ("vacating an
    adverse judgment and remanding for a new trial in which the
    protected material and its fruits are excluded from evidence" is
    adequate remedy to erroneous disclosure of privileged material).
    In short, an appellate court on postjudgment appeal cannot
    prevent privileged communications from having been disclosed to
    the developer plaintiffs, but it can protect the trust
    defendants from the harm arising from those communications
    having been used against them at trial.   If the trust defendants
    were prejudiced at trial by the admission of evidence derived
    from the privileged communications revealed pursuant to the
    order, an appellate court may grant them a new trial, where no
    evidence derived from those communications will be admitted.
    Notably, the trust defendants here are claiming a right of
    immediate appeal from a discovery order, which commonly involves
    claims of denial of rights or invasions of privilege.    See
    
    Borman, 378 Mass. at 784
    (orders compelling witness testimony
    "are among the most common of everyday incidents to the process
    of disposing of cases, and objections on the ground of privilege
    . . . are frequently raised" [citation omitted]).   Discovery
    orders may direct a witness to testify at a deposition about
    13
    information that a witness claims would be self-incriminating,
    see 
    id. at 781-782,
    or that a witness claims is protected by
    various privileges other than the attorney-client privilege,
    such as the spousal privilege or the psychotherapist-patient
    privilege.   Discovery issues regarding the scope of the
    attorney-client privilege -- and its application to documents
    sought in discovery -- may arise whenever a party produces a
    privilege log identifying documents that the party refuses to
    disclose because they purportedly contain protected attorney-
    client communications or attorney work product.   Whenever a
    judge orders disclosure in any of these discovery disputes, the
    aggrieved party can claim that its rights cannot be fully
    vindicated on appeal, because otherwise protected communications
    or documents will be revealed that the party was entitled to
    keep confidential.   But if that intrinsic harm were to suffice
    to make all such discovery orders appealable under the doctrine
    of present execution, we would be inviting "the inundation of
    appellate dockets with what have heretofore been regarded as
    nonappealable matters" (citation omitted), 
    Cronin, 392 Mass. at 529
    , with the resulting delays and increased litigation costs
    that come with piecemeal interlocutory appeals.   Where a
    postjudgment appeal offers a viable, albeit imperfect, remedy,
    we will not grant a right to interlocutory appeal from a
    discovery order simply because it involves an issue of
    14
    privilege.   We thus conclude that orders requiring the
    disclosure of privileged material, such as the order in this
    case, are not categorically irremediable, and therefore are not
    appealable under the doctrine of present execution.5
    We note that our analysis is consistent with that of other
    courts.   The Supreme Court was confronted with this same
    question, interpreting the Federal collateral order doctrine, in
    Mohawk Indus., 
    Inc., 558 U.S. at 103
    .   Explaining that the Court
    "routinely require[s] litigants to wait until after final
    judgment to vindicate valuable rights, including rights central
    to our adversarial system," 
    id. at 108-109,
    the Court noted that
    an erroneous privilege disclosure order is akin to other common
    errors that may take place throughout the life of a case.   The
    5 The trust defendants note that we stated in Preventive
    Med. Assocs., Inc. v. Commonwealth, 
    465 Mass. 810
    , 823 (2013),
    that the harm to a party from the disclosure of privileged
    attorney-client communications to an adversary "could be
    irreparable." We recognized the potential for irreparable harm
    in that case in the context of requiring judicial supervision of
    the protocol used by the Commonwealth to search the electronic
    mail (e-mail) messages of a criminal defendant -- which were
    seized pursuant to a search warrant -- where the e-mail messages
    may contain privileged attorney-client communications, not in
    the context of deciding whether to allow an immediate appeal
    from a discovery order in a civil case under the doctrine of
    present execution. See 
    id. We recognize
    here that there is
    intrinsic irreparable harm where a judge erroneously orders the
    disclosure of privileged communications, but conclude that this
    intrinsic harm alone does not suffice to require a right to
    interlocutory appeal under the doctrine of present execution
    where there is a viable postjudgment remedy for the use of this
    privileged information against the party at trial.
    15
    Court concluded that such errors may be remedied in the same way
    as other erroneous evidentiary rulings:    by reversing the
    judgment and remanding for further proceedings in which the
    protected material and its fruits are inadmissible in evidence.
    
    Id. For those
    reasons, interlocutory appeals from attorney-
    client privilege disclosure orders under 28 U.S.C. § 1291 are
    not permitted as of right under the Federal collateral order
    doctrine.   
    Id. at 114.
      Numerous State appellate courts have
    reached the same conclusion as a matter of State law.    See,
    e.g., Melia v. Hartford Fire Ins. Co., 
    202 Conn. 252
    , 258-259
    (1987); Expedia, Inc. v. Columbus, 
    305 Ga. App. 450
    , 453 (2010);
    Abrams v. Cades, Schutte, Fleming & Wright, 
    88 Haw. 319
    , 325
    (1998).
    Ultimately, the doctrine of present execution represents a
    balancing act that weighs the harm to cost-effective litigation
    arising from piecemeal interlocutory appeals against the harm
    that a litigant may suffer from a trial court order that is
    irremediable on postjudgment appeal.    We conclude that the sheer
    volume of potential appeals that would be permitted by including
    privilege-related discovery orders within the doctrine of
    present execution, and the inevitable adverse impact on judicial
    efficiency, outweighs the intrinsic harm that potentially might
    be suffered by an aggrieved party who is denied an immediate
    right to appeal.
    16
    In reaching this balance, we note that denying a litigant
    the right to a full interlocutory appeal under the doctrine of
    present execution does not bar a litigant from moving or
    petitioning for immediate appellate review of an interlocutory
    order.   Where a party believes that the legal questions at issue
    regarding a discovery order are so significant or novel that
    they warrant interlocutory appeal, the party may generally
    request the Superior Court judge to report the decision to the
    Appeals Court under Mass. R. Civ. P. 64.   Or the party may
    petition a single justice of the Appeals Court under G. L.
    c. 231, § 118, first par., and seek redress from the single
    justice, as the trust defendants did here, or ask the single
    justice to refer the petition to a full panel of the Appeals
    Court.   And where a party or nonparty feels so strongly about
    the injustice of an order compelling discovery that it is
    willing to suffer the sanctions that might arise from disobeying
    the order, the party or witness can obtain full appellate review
    of the order as a matter of right by refusing to comply with the
    order and appealing from the resulting order of dismissal or
    contempt.   See 
    Cronin, 392 Mass. at 528
    , citing Matter of Roche,
    
    381 Mass. 624
    , 625 n.1 (1980).6   We are satisfied that this
    6 We recognize that, as here, an attorney who denies the
    existence of an attorney-client relationship with the moving
    party regarding the subject matter of the litigation is not
    going to refuse to testify and risk a contempt finding. But we
    17
    collection of alternative remedies will adequately protect the
    rights of litigants who are egregiously harmed by interlocutory
    discovery orders.
    2.     Partial denial of motion for protective order based on
    trust defendants' claim of attorney-client privilege.    Having
    concluded that the trust defendants are not entitled under the
    doctrine of present execution to appeal from the partial denial
    of their motion for a protective order, based on their claim
    that they had an attorney-client relationship with Levin
    regarding the sale of the property before the fire, we have two
    options.    We can exercise our discretion under our
    superintendence authority to reach the merits of this appeal,
    where the issue "has been briefed fully by the parties . . .
    [and] raises a significant issue" regarding attorney-client
    relationships and the doctrine of privilege, "and addressing it
    would be in the public interest."    
    Marcus, 462 Mass. at 153
    .    Or
    we can dismiss the appeal, and allow the single justice of the
    Appeals Court to decide the G. L. c. 231, § 118, first par.,
    petition that he stayed pending resolution of the appeal.    We
    decline to grant a right of interlocutory appeal to a party in a
    civil proceeding simply because that avenue of appeal is not
    available. We do not address whether a right of interlocutory
    appeal would be appropriate in these circumstances if the appeal
    concerned a privilege issue in a criminal or grand jury
    proceeding. Cf. Matter of a R.I. Grand Jury Subpoena, 
    414 Mass. 104
    , 110 (1993); Matter of a Grand Jury Subpoena, 
    411 Mass. 489
    ,
    494 (1992).
    18
    exercise the first option, and after considering the trust
    defendants' argument, we conclude that the motion judge's order
    cannot stand based on the limited findings that he made.     We
    therefore vacate his order and remand the matter to the motion
    judge for further factual findings and reconsideration of the
    motion in light of those additional findings.   We express no
    view as to how the motion should ultimately be decided.    After
    the judge makes those findings and issues a new order, the
    aggrieved party may avail itself of the options we have
    identified for interlocutory appellate review -- i.e.,
    requesting the judge to report his ruling to a panel of the
    Appeals Court or filing a petition under § 118, first par. --
    but, for reasons we have already explained, will not be entitled
    to an interlocutory appeal under the doctrine of present
    execution.
    a.   Standard of review.   A judge's ultimate conclusion as
    to whether an attorney-client relationship existed is a mixed
    question of law and fact, which we review de novo.   See McCarthy
    v. Slade Assocs., Inc., 
    463 Mass. 181
    , 190 (2012), quoting
    Commissioner of Revenue v. Comcast Corp., 
    453 Mass. 293
    , 303
    (2009) ("Mixed questions of law and fact, such as whether there
    has been a waiver, generally receive de novo review"); 2 P.R.
    Rice, Attorney-Client Privilege in the United States § 11.38, at
    1253-1255 (2017) (most questions concerning issues of attorney-
    19
    client privilege involve "a mixture of law and fact").     In doing
    so, we accept a judge's findings of fact "unless clearly
    erroneous, and due regard shall be given to the opportunity of
    the trial court to judge . . . the credibility of the
    witnesses."   Mass. R. Civ. P. 52 (a), as amended, 
    423 Mass. 1408
    (1996).
    b.    Summary of the evidence and the judge's findings.    It
    was undisputed that Levin represented the Masons, as the sellers
    of the property, in connection with the purchase and sale
    agreement, and that he was identified as their attorney of
    record on the agreement that was signed in September 2012.    The
    question before the judge was whether Levin had also established
    an attorney-client relationship with the trust defendants, who
    were the buyers in this transaction.   Levin testified that he
    had not; the trust defendants testified that he had.
    Levin acknowledged that he had represented the trust
    defendants in a large number of matters, including real estate
    matters, for over twenty years, and that he did over ninety per
    cent of the trust defendants' legal work. He testified that, in
    the spring of 2012, when he learned that the trust defendants
    were seeking to make an offer on the property, he was
    representing the trust defendants in a number of other real
    estate transactions.   In Levin's electronic mail messages with
    the trust defendants, he discussed the purchase and sale
    20
    agreement in conjunction with other pending matters.   The trust
    defendants and Levin agreed that, because he was representing
    the Masons as the sellers, the trust defendants would identify
    Miriam Marcus as their attorney of record in the agreement.
    Levin admitted that he never communicated with Miriam Marcus,
    and instead communicated directly with the trust defendants
    because he knew that Martin always negotiated real estate
    transactions personally.   Levin sent draft documents to the
    trust defendants for review, prepared a power of attorney form
    for Martin so that he could sign the purchase and sale agreement
    on behalf of the Grossman Munroe Trust, and acknowledged having
    "many conversations" with Martin concerning the transaction
    after the agreement was signed in September 2012, particularly
    about deadlines in the agreement and seeking an extension to
    perform due diligence obligations.   Levin also testified that he
    discussed with the trust defendants their concerns about
    financing, construction, and permits related to the division of
    condominium units on the property; those issues were
    incorporated into a rider to the purchase and sale agreement.
    Levin billed the Masons and the trust defendants each one-half
    of his fee in connection with the purchase and sale transaction.
    The bill sent to the trust defendants listed the Masonic Temple
    transaction with other pending real estate matters on which he
    represented the trust defendants.
    21
    Throughout his testimony, Levin contended that he never
    provided particularized legal advice or assistance to the trust
    defendants in connection with the sale of the property, but did
    provide advice "affect[ing] both sides" at group meetings
    regarding various issues.    Levin characterized his role in the
    matter as a simple one:     the parties had discussed agreed-upon
    terms, and he worked to memorialize them into a working purchase
    and sale agreement.   He made himself available to answer
    questions from the defendants, but he described these
    communications as "direction, not [advice]."    Levin testified
    that he explicitly told the trust defendants that he would not
    be able to represent them in the purchase and sale transaction.
    The trust defendants disputed Levin's testimony.      Seymour
    Marcus testified that Levin had explicitly told him that Levin
    was going to represent both sides, and that Levin had
    represented opposing parties to a transaction with them before,
    in the context of lenders and borrowers and also buyers and
    sellers.   Marcus stated that Levin offered particularized legal
    advice in meetings -- without the Masons present -- on
    permitting and construction issues regarding the property and on
    what "[his] liabilities are to the Masons."    He said that Levin
    instructed them to list Miriam Marcus as their attorney solely
    as a formality.
    22
    Martin testified that he never executed a real estate
    transaction without representation, and virtually always used
    Levin to negotiate agreements and draft documents.   Martin
    contradicted Levin's testimony that Levin merely wrote the terms
    that the parties had agreed upon, claiming that Levin proposed
    amendments to the purchase and sale agreement and made
    suggestions and comments throughout the negotiation process.
    Martin also testified that Levin never told the trust defendants
    that he would be unable to represent them.   Rather, Martin
    testified, Levin made clear that he was representing both sides,
    and asked the trust defendants to list Miriam Marcus as their
    attorney only to avoid the appearance of impropriety.
    At the close of the evidentiary hearing, the judge
    announced his findings and subsequent order.   Because it was
    undisputed that the trust defendants approached Levin for legal
    advice -- and indeed received such advice -- regarding their
    exposure to insurer claims and other liability after the fire,
    the judge first found that there was an attorney-client
    relationship between Levin and the trust defendants after the
    fire.   With respect to the matters involving the purchase and
    sale agreement before the fire, the judge found that the Masons
    and the trust defendants shared a common interest in the sale,
    transfer, and development of the property, but not a common
    23
    interest in the sense "that their interests were aligned with
    regard to this transaction."   He noted:
    "[A] purchase and sale agreement generally is designed to
    protect the rights and enforce the obligations of a buyer
    and seller, which almost by definition are antagonistic one
    to the other. And in a transaction of this complexity, it
    seems impossible that a single attorney could represent
    both sides in a very complex and sophisticated real estate
    transaction."
    The judge continued:
    "I accept the testimony as I've heard it that there
    was a longstanding relationship between Mr. Levin and
    Mr. Marcus and his various ventures that extended
    perhaps up to [twenty-five] years and involved
    countless real estate transactions . . . where Mr.
    Levin served essentially as in-house counsel for Mr.
    Marcus and his various holdings. And I acknowledge
    that . . . any communications [with Levin] as to all
    of those real estate transactions in the past would
    fall under the attorney-client umbrella that Mr. Levin
    had with Mr. Marcus and his entities. That does not
    mean in this particular transaction, however, that
    . . . Mr. Levin necessarily represented Mr. Marcus and
    Mr. Martin.
    "A party asserting a privilege has the burden of
    proving that the privilege exists. I don't find in
    this case that the [trust defendants have] proved to
    my satisfaction that Mr. Levin acted as the attorney
    for Mr. Marcus and Mr. Martin with regard to the
    negotiations leading to the signing of a [purchase and
    sale agreement] or with regard to negotiations leading
    to an extension of that [purchase and sale
    agreement]."
    The judge thus found that there was no attorney-client
    relationship between the trust defendants and Levin with respect
    to the purchase and sale transaction before the fire.
    24
    c.   Analysis.   On appeal, the trust defendants do not
    contend that there was an express contract whereby Levin agreed
    to represent them with respect to the Masonic Temple purchase
    and sale transaction.   Rather, they argue that the attorney-
    client relationship was implied as a matter of law by the
    conduct of the parties, particularly based on their reasonable
    belief that Levin was representing them.    An attorney-client
    relationship may be impliedly formed "when (1) a person seeks
    advice or assistance from an attorney, (2) the advice or
    assistance sought pertains to matters within the attorney's
    professional competence, and (3) the attorney expressly or
    impliedly agrees to give or actually gives the desired advice or
    assistance. . . .    In appropriate cases the third element may be
    established by proof of detrimental reliance, when the person
    seeking legal services reasonably relies on the attorney to
    provide them and the attorney, aware of such reliance, does
    nothing to negate it" (citation omitted).    DeVaux v. American
    Home Assur. Co., 
    387 Mass. 814
    , 817-818 (1983).
    The judge's findings raise issues both of law and of fact,
    none of which can be resolved without remand to the motion judge
    for further findings.   The issue of law is that the judge, after
    finding that the interests of the buyer and seller in this
    purchase and sale transaction were "antagonistic" to each other,
    stated that "in a transaction of this complexity, it seems
    25
    impossible that a single attorney could represent both sides in
    a very complex and sophisticated real estate transaction."    It
    is not clear from the record precisely what the judge meant by
    this statement, especially where the judge found that Levin
    represented both the trust defendants and the Masons after the
    fire, when their interests remained adverse.7
    It is not ethically impossible for an attorney to represent
    clients with adverse interests.   Under Mass. R. Prof. C.
    1.7 (a), as amended, 
    430 Mass. 1301
    (1999) -- the version of
    rule 1.7 in effect at the time of this transaction -- an
    attorney could represent clients with directly adverse
    interests, even in complex real estate transactions, where the
    attorney reasonably believed that his or her representation of
    each client would not adversely affect the relationship with the
    other client and each affected client consented after
    consultation.8   But even where an attorney would have violated
    7 The Masons later sued the trust defendants, and Levin
    testified that he only stepped aside from representing the trust
    defendants after that lawsuit commenced.
    8 Subsequent to the transaction at issue in this case, our
    rules of professional responsibility were amended. Under the
    current Mass. R. Prof. C. 1.7, as appearing in 
    471 Mass. 1335
    (2015), an attorney may represent clients with directly adverse
    interests where the attorney reasonably believes that he or she
    will be able to provide competent and diligent representation to
    each affected client, the representation is not otherwise
    prohibited by law, the representation does not involve the
    assertion of a claim by one client against another in the same
    26
    this rule by jointly representing clients with adverse interests
    without consent, the attorney still would have had a separate
    attorney-client relationship with each client.     See RFF Family
    Partnership, LP v. Burns & Levinson, LLP, 
    465 Mass. 702
    , 721
    (2013).   And where there is an attorney-client relationship,
    even one that an attorney ethically should not have entered into
    without consent because of a conflicting representation, the
    client is entitled to protect confidential communications with
    the attorney.   See 
    id., quoting In
    re Teleglobe Communications
    Corp., 
    493 F.3d 345
    , 369 (3d Cir. 2007) ("even where a law firm
    actually violates Mass. R. Prof. C. 1.7[a] by representing two
    clients with adverse interests without the consent of each
    client, 'counsel's failure to avoid a conflict of interest
    should not deprive the client of the privilege'").
    Where we cannot be sure what the motion judge meant by his
    finding that it seems "impossible" for Levin, who was already
    representing the Masons with respect to the sale of its
    property, also to represent the trust defendants with respect to
    that transaction, we believe it prudent to remand the matter to
    the judge for clarifying findings on this issue.    It is unclear
    what role, if any, that finding played in his ultimate
    litigation or proceeding, and each affected client gives
    informed written consent.
    27
    determination that Levin did not enter into an attorney-client
    relationship with the trust defendants until after the fire.
    We must also remand for further findings because we cannot
    evaluate whether the judge's findings were clearly erroneous
    without credibility findings regarding the conflicting testimony
    of Levin and the trust defendants.   For example, the judge did
    not resolve contradictory testimony as to whether Levin
    explicitly told the trust defendants that he could not represent
    them because he was simultaneously representing the Masons,
    which bears on the trust defendants' claim of detrimental
    reliance.   The judge found only that the trust defendants had
    failed to satisfy their burden of proving that they had an
    attorney-client relationship with Levin regarding the
    negotiation of the purchase and sale agreement and its
    extension, but he did not explain why.
    Importantly, the judge did not address the undisputed fact
    that Levin billed both the Masons and the trust defendants for
    his legal work regarding this transaction, splitting his fee
    equally between them.   Where, as here, an attorney bills an
    existing client for legal services, and where the client pays
    for those services, it is reasonable to infer that they had an
    attorney-client relationship with regard to those services.    See
    Williams v. Ely, 
    423 Mass. 467
    , 476 (1996) ("It seems clear that
    [the client] would not have contributed toward payment of [the
    28
    law firm's] bills if they had received no legal advice from the
    firm").    An attorney's billing for legal services and a client's
    payment of the bill for such services may not be dispositive of
    the existence of an attorney-client relationship, but a finding
    of no attorney-client relationship with respect to legal
    services that were billed and paid warrants an explanation.    See
    Matter of Stern, 
    425 Mass. 708
    , 712-713 (1997) (trustee acted as
    legal advisor and attorney-client relationship was formed where,
    inter alia, trustee was paid fees specifically to act as
    attorney); Droz v. Karl, 
    736 F. Supp. 2d 520
    , 524-525 (N.D.N.Y.
    2010) (while not dispositive, payment of fee to attorney is
    "indicator[] of an attorney-client relationship").
    As to this issue, we note that an attorney-client
    relationship may impliedly be formed when an attorney provides
    "advice or assistance" (emphasis added).    
    DeVaux, 387 Mass. at 817-818
    .   Where "advice" has been defined as "[g]uidance
    offered," see Black's Law Dictionary 65 (10th ed. 2014), we may
    interpret "assistance" here to mean "services rendered."    See 1
    P.R. Rice, Attorney–Client Privilege in the United 
    States, supra
    at § 7.10, at 1273-1277 ("Legal assistance requires the
    involvement of the judgment of a lawyer in his capacity as a
    lawyer," and it "requires an attorney to render the type of
    services that his education and certification to practice
    qualify him to render for compensation" [quotation omitted]);
    29
    Sheinkopf v. Stone, 
    927 F.2d 1259
    , 1266 (1st Cir. 1991)
    (describing attorney's obtaining of party's check and having
    that party sign various documents as "assistance . . .
    rendered," and distinguishing "legal advice" from actual,
    concrete transactions).   The question whether Levin provided
    "assistance" to the trust defendants that created an attorney-
    client relationship is related to, but distinct from, the
    question whether he provided them with legal "advice."    The
    motion judge may wish to consider this issue on remand.
    Conclusion.   The order of the Superior Court judge
    partially denying the trust defendants' motion for a protective
    order is vacated, and the matter is remanded for further
    findings consistent with this opinion and for reconsideration of
    the motion in light of those findings.
    So ordered.