Esso Standard Oil Co. v. López-Freytes ( 2008 )


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  •            United States Court of Appeals
    For the First Circuit
    No. 07-1218
    ESSO STANDARD OIL CO. (PUERTO RICO),
    Plaintiff, Appellee,
    v.
    CARLOS W. LÓPEZ-FREYTES, in his personal and
    official capacities as President of the Puerto Rico
    Environmental Quality Board; FLOR DEL VALLE-LÓPEZ, in her
    official capacity as Associate Member of the Puerto Rico
    Environmental Quality Board; ANGEL BERRÍOS-SILVESTRE, in his
    official capacity as Associate Member of the Puerto Rico
    Environmental Quality Board; NORMAN VELÁZQUEZ-TORRES, in his
    official capacity as Attorney of the Puerto Rico
    Environmental Quality Board,
    Defendants, Appellants.
    APPEAL FROM THE UNITED STATES DISTRICT COURT
    FOR THE DISTRICT OF PUERTO RICO
    [Hon. Justo Arenas, U.S. Magistrate Judge]
    Before
    Torruella, Circuit Judge,
    Baldock,* Senior Circuit Judge,
    and Lipez, Circuit Judge.
    Salvador J. Antonetti-Stutts, Solicitor General, Department of
    Justice, with whom Luis José Torres-Asencio, Assistant Solicitor
    General, Eduardo A. Vera-Ramírez, Eileen Landrón-Guardiola, Luis A.
    Rodríguez-Muñoz, and Landrón & Vera, LLP were on brief, for
    appellants.
    Charles G. Cole, with whom Alice E. Loughran, Steptoe &
    *
    Of the Tenth Circuit, sitting by designation.
    Johnson LLP, Lawrence P. Riff, Jason Levin, John F. Nevares, and
    John F. Nevares & Assoc., PSC were on brief, for appellee.
    April 10, 2008
    -2-
    TORRUELLA, Circuit Judge.              This is an appeal from the
    district court's issuance of an order permanently enjoining the
    defendants –- several members and officials of the Puerto Rico
    Environmental Quality Board ("EQB") -- from imposing a $76 million
    fine on the plaintiff, Esso Standard Oil Company ("Esso").                       On
    appeal, the defendants argue that the district court should have
    abstained from exercising jurisdiction pursuant to the Younger
    abstention   doctrine    and,       in   any    event,   the    court    erred   in
    concluding that there existed bias necessitating the imposition of
    the   injunction.      After    careful        consideration,    we     affirm   the
    district court's order.
    I.    Background
    This case comes to us on appeal for the second time.1
    Given that the background facts are outlined extensively in our
    prior opinion, see Esso Standard Oil Co. v. Cotto, 
    389 F.3d 212
    ,
    213-18 (1st Cir. 2004) ("Esso I"), we need not repeat them here in
    great detail.       In brief, the case involves an underground fuel
    storage system at a service station in Barranquitas, Puerto Rico.
    Beginning in 1979, Esso had leased storage tanks and other fuel
    supplies to the station and in 1991 replaced the entire underground
    storage system.      Between August 1998 and October 1999, the EQB
    issued three orders directing Esso to test the fuel storage system.
    1
    Between these two appeals, Esso filed for panel rehearing. We
    denied the motion and directed Esso to renew its request for
    injunctive relief with the district court.
    -3-
    Those investigations revealed and recovered about 550 gallons of
    spilled fuel.
    Despite   Esso's     efforts     to    comply   with    the     EQB's
    directives, the EQB issued a show cause order on May 21, 2001,
    proposing a $76 million fine against Esso for its failure to notify
    the EQB upon initial discovery of the fuel leakage and its failure
    to   timely    investigate,      clean   up,   and   remedy   the    harm.2      In
    September 2002, the EQB initiated hearings on this proposed penalty
    against Esso.     The hearings were marked by contentious debates and
    allegations of severe bias.          See Esso I, 
    389 F.3d at 215
    .              Esso
    filed numerous motions, including two motions seeking dismissal of
    the proceedings.3
    In March 2004, Esso filed suit in federal court, seeking
    a preliminary injunction to prevent the EQB from imposing the
    massive fine on the ground that the proceedings were so plagued by
    conflict and bias that they violated Esso's due process rights.
    2
    Pursuant to statute, all fines collected by the EQB are
    deposited into a discretionary fund administered by the EQB. 
    P.R. Laws Ann. tit. 12, § 1136
    (f).
    3
    Esso immediately filed an appeal in the Puerto Rico Court of
    Appeals seeking dismissal of the hearings on statute of limitations
    grounds. The court dismissed the appeal, asserting that in the
    absence of a final judgment, it had no authority to review the
    appeal of an agency order.     Esso Standard Oil Co. v. Junta de
    Calidad Ambiental, Nos. OA-01-AG-26 & OA-99-AG-109, 
    2002 WL 1438761
    , at *4 (P.R. Cir. May 1, 2002) (citing 
    P.R. Laws Ann. tit. 3, § 2172
    ). In November 2003, Esso moved the EQB Hearing Examiner
    for expedited recommendation of dismissal alleging constitutional
    due process violations. Neither the Hearing Examiner nor the EQB
    Governing Board has ruled on the motion.
    -4-
    Although the district court made several findings of bias, it
    dismissed the case for lack of jurisdiction pursuant to the Younger
    abstention doctrine.   On appeal, we expressed serious concern with
    the undisputed evidence of structural and actual bias in the case.
    Esso I, 
    389 F.3d at 218-19
    .    We concluded, however, that despite
    this evidence of bias, federal intervention was inappropriate under
    the abstention exception recognized in Gibson v. Berryhill, 
    411 U.S. 564
     (1973), because Esso had not yet demonstrated irreparable
    harm.   Esso I, 
    389 F.3d at 221-25
    .    Specifically, we found that
    Esso could seek interlocutory relief from the Puerto Rico courts,4
    and we affirmed the district court's decision to abstain.
    A.   Interlocutory Appeals
    Soon after the issuance of our opinion, Esso filed a
    petition for interlocutory review with the Puerto Rico Court of
    Appeals, asserting jurisdiction pursuant to MCS Insurer and arguing
    that the EQB administrative proceedings are fatally biased and
    4
    In 2002, Esso had filed an interlocutory appeal before the
    Puerto Rico Court of Appeals alleging that the suit was barred by
    the statute of limitations. The court denied the appeal on the
    basis of 
    P.R. Laws Ann. tit. 3, § 2171
    , which requires a final
    order and exhaustion of administrative process before judicial
    review. See Esso I, 
    389 F.3d at 223
    . We noted, however, that an
    intervening decision by the Puerto Rico Supreme Court had cast
    doubt on that prior ruling: the Puerto Rico Supreme Court had
    recognized an exception to § 2172 for alleged constitutional
    violations that rose to the level of an "intense grievance" that
    was supported by "specific, well defined facts."       Id. at 224
    (citing Oficina de la Procuradora del Paciente v. Aseguradora MCS,
    2004 T.S.P.R. at ___, 162 D.P.R. at ___, 
    2004 WL 2212782
     ("MCS
    Insurer")). We concluded that "Esso's claim might well meet th[at]
    standard." 
    Id.
    -5-
    violate its due process rights. The following day, the Puerto Rico
    Court of Appeals dismissed the appeal and denied the accompanying
    request to stay the EQB's administrative proceedings.                 It rejected
    the   contention     that    MCS    Insurer   created   an    exception    to   the
    statutory administrative exhaustion requirements applicable in this
    case: "We resolve that insofar as the administrative process has
    not concluded and the 'total denial' object of this appeal is not
    a final decision of the agency, but an 'implicit' interlocutory
    resolution, we are barred from addressing the same." Esso Standard
    Oil Co. v. Junta de Calidad Ambiental, Case No. OA-99-AG-26 & OA-
    99-AG-109, 
    2004 WL 3199104
    , at *5 (P.R. Cir. Dec. 3, 2004) ("Esso,
    P.R. Court of Appeals"); see also 
    P.R. Laws Ann. tit. 3, § 2172
    .
    The appeal was dismissed for lack of jurisdiction.                
    Id.
    Three days later, Esso petitioned for writ of certiorari
    to the Puerto Rico Supreme Court, asserting that the Puerto Rico
    Court   of    Appeals       had    erroneously    declared     that   it    lacked
    jurisdiction    to    review       Esso's   due   process    allegations.       The
    following day, the Puerto Rico Supreme Court summarily denied the
    requested writ, stating: "As to the petition for certiorari and the
    motion in aid of jurisdiction, [it is] denied at this stage of the
    proceedings."      Esso Standard Oil Co. v. P.R. Env't Quality Bd.,
    Case No. CC-2004-1155 (P.R. Dec. 7, 2004) ("Esso, P.R. Supreme
    Court").
    -6-
    Esso then returned here and filed for panel rehearing,
    arguing that it was now able to demonstrate irreparable harm
    because   the   Supreme    Court   of    Puerto   Rico   had   held   that
    interlocutory appeal was unavailable to Esso.        Although we agreed
    that the intervening developments had a significant impact upon a
    determination of the appropriateness of federal intervention, we
    concluded that the appropriate procedure was for Esso to renew its
    request for a preliminary injunction in federal district court.
    B.    Renewed Motion for Preliminary Injunction
    On February 4, 2005, Esso filed a renewed and unopposed
    motion for preliminary injunction in the district court.               In
    accordance with our decision in Esso I, the district court focused
    on the issue of whether Esso was able to show irreparable harm in
    the absence of federal intervention.       The court concluded that the
    denials by the Puerto Rico Court of Appeals and Supreme Court
    provided "unquestionable proof that as a matter of both fact and
    law, the only element preventing federal intervention in this case
    has been removed from the picture."          Esso Standard Oil Co. v.
    López-Freytes, No. 03-2319 (D.P.R. Mar. 11, 2005) (order granting
    preliminary injunction).     The court granted Esso's request for a
    preliminary injunction and ordered the defendants to show cause as
    to why the preliminary injunction should not be converted to a
    permanent injunction.     The defendants opposed such a conversion on
    the ground that they had not received notice of the consolidation
    -7-
    of the preliminary injunction hearing and the trial on the merits
    and thus had not presented any witnesses or evidence. The district
    court concluded that it was premature to convert the preliminary
    injunction    into   a   permanent    injunction       without   giving    the
    defendants an opportunity to controvert the allegations of bias.
    Soon   thereafter,      Esso     filed   a   motion    for   summary
    judgment, opposed by the defendants, contending that there were no
    disputed issues of material fact.          In November 2006, the district
    court entered summary judgment for Esso and issued a permanent
    injunction.    See Esso Standard Oil Co. v. López-Freytes, 
    467 F. Supp. 2d 156
     (D.P.R. 2006).    In a separate order, the court stated:
    [D]efendants are permanently enjoined from
    conducting any and all administrative hearings
    and proceedings against Esso related to the
    penalty provision of the order to show cause
    issued on May 21, 2001 in In re Esso Standard
    Oil Company, Case No. OA-99-TE-102.      It is
    further ordered that the defendants are
    permanently   enjoined    from   issuing   any
    judgments    or    resolutions,    final    or
    interlocutory, in said matter, and from
    instituting, conducting and/or prosecuting any
    administrative penalty proceedings against
    Esso based on or arising from the facts and
    events described in said order to show cause.
    Esso Standard Oil Co. v. López-Freytes, No. 03-2319 (D.P.R. Nov. 7,
    2006) (order granting permanent injunction).              Defendants appeal
    this order.
    II.    Discussion
    The defendants make three separate challenges: (1) the
    district court was required to abstain pursuant to the Younger
    -8-
    doctrine; (2) the evidence does not support a finding of bias; and
    (3) the scope of the permanent injunction is impermissibly broad.
    A    district   court's   decision     to   grant     a   permanent
    injunction involves factual, legal, and discretionary components.
    We therefore apply different standards of review: questions of law
    are reviewed de novo and the scope of the injunction is reviewed
    for abuse of discretion.         Aponte v. Calderón, 
    284 F.3d 184
    , 191
    (1st Cir. 2002). In this case, the injunction was issued following
    a grant of summary judgment and, accordingly, we view the facts in
    the light most favorable to the nonmoving parties, drawing all
    reasonable inferences in their favor.           See Ramírez-Carlo v. United
    States, 
    496 F.3d 41
    , 46 (1st Cir. 2007).           Insofar as the threshold
    issue involves the application of the Younger abstention doctrine,
    this is a legal question that we review de novo.                  See Brooks v.
    N.H. Sup. Ct., 
    80 F.3d 633
    , 637 (1st Cir. 1996) ("[W]e must review
    de   novo   the    essentially   legal       determination   of    whether   the
    requirements for abstention have been met.").
    A.   Younger Abstention
    In the absence of extraordinary circumstances, interests
    of comity and the respect for state processes demand that federal
    courts should abstain from interfering with ongoing state judicial
    proceedings.       See, e.g., Younger v. Harris, 
    401 U.S. 37
     (1971);
    Middlesex Co. Ethics Comm. v. Garden State Bar Ass'n, 
    457 U.S. 423
    (1982).     Although initially applied to state criminal actions, the
    -9-
    abstention doctrine has been extended to other proceedings that
    implicate important state interests, including the state-level,
    quasi-judicial, administrative proceeding at issue here.                       See
    Maymó-Meléndez v. Alvarez-Ramírez, 
    364 F.3d 27
    , 31 n.3 (1st Cir.
    2004)   (enumerating        the   various     applications    of    the   Younger
    doctrine).     Generally, insofar as the state proceedings evince "no
    showing of bad faith, harassment, or some other extraordinary
    circumstance that would make abstention inappropriate, the federal
    courts should abstain."           Middlesex Co. Ethics Comm., 
    457 U.S. at 435
    . Extraordinary circumstances include those situations in which
    "core constitutional values are threatened during an ongoing state
    proceeding and there is a showing of irreparable harm that is both
    great and immediate." Maymó-Meléndez, 
    364 F.3d at 37
     (internal
    quotation marks omitted).          Among those extraordinary circumstances
    are   cases    in   which    extreme   bias    completely    renders      a   state
    adjudicator incompetent and inflicts irreparable harm upon the
    petitioner. Gibson v. Berryhill, 
    411 U.S. at 577
    ; accord Kugler v.
    Helfant, 
    421 U.S. 117
    , 125 n.4 (1975) (recognizing Gibson bias as
    an example of the "exceptional circumstances" which warrant federal
    intervention).
    In our prior opinion, we held that this case "lies
    squarely   within     Younger's     domain"     and   that   Esso   had   clearly
    established the presence of bias which raised the kind of concerns
    permitting interim federal intervention pursuant to Gibson.                   Esso
    -10-
    I, 
    389 F.3d at 219-20
    .      We rejected the argument that the eventual
    availability     of    judicial     review   at   the   conclusion      of   the
    administrative      proceedings     was   sufficient     to    ameliorate    any
    constitutional injury inflicted upon Esso because it is currently
    in the midst of those allegedly infirm proceedings. 
    Id., at 220-21
    ("[T]he availability of judicial review of a final agency decision
    is insufficient to avoid the irreparable harm that inheres in the
    biased administrative proceeding itself.").              In the intervening
    time, nothing has altered those conclusions and we have neither
    occasion nor need to revisit those rulings.             See United States v.
    Moran, 
    393 F.3d 1
    , 7 (1st Cir. 2004) ("The law of the case doctrine
    'posits that when a court decides upon a rule of law, that decision
    should continue to govern the same issues in subsequent stages in
    the same case.'" (quoting Arizona v. California, 
    460 U.S. 605
    , 618
    (1983))).
    In the last appeal, we also concluded, however, that Esso
    was   unable   to     demonstrate    irreparable    harm      because   of   the
    availability of immediate interlocutory relief through the Puerto
    Rico courts.   Esso now returns to us with evidence that such relief
    is unavailable: Esso avers that it has sought, and been denied,
    interlocutory relief in the Puerto Rico Court of Appeals and the
    Puerto Rico Supreme Court.          We, therefore, revisit our analysis
    under Gibson with respect to the irreparable harm issue.
    -11-
    The    defendants      assert       that   Esso   still   fails    to
    demonstrate irreparable harm because: (1) the Puerto Rico courts'
    denial   of   Esso's   appeals    was     a    merits    determination,     not
    jurisdictional; and (2) Esso is not without relief as it has
    several other options, such as filing for mandamus or submitting a
    new claim in Puerto Rico Superior Court.             We find neither argument
    to be availing here.
    With   respect   to    the    first    argument,    the   defendants
    contend that the Puerto Rico Court of Appeals rejected Esso's
    petition for interlocutory appeal because Esso had failed to
    demonstrate that the alleged violations were still ongoing.                 In
    essence, the defendants argue that Esso was not denied the option
    of interlocutory review; rather, Esso failed on the merits.               Given
    the clear language of the opinion of the Puerto Rico Court of
    Appeals, we cannot agree.
    The day after Esso submitted its forty-four page petition
    for interlocutory review the court of appeals issued an opinion
    denying the request.    The opinion expressly states that the basis
    for the denial was jurisdictional:
    We resolve that insofar as the administrative
    process has not concluded that the 'total
    denial' object of this appeal is not a final
    decision of the agency, but an 'implicit'
    interlocutory resolution, we are barred from
    addressing the same.   Pursuant to the legal
    system prevailing in our jurisdiction, this
    appellate   forum   should   not   intervene,
    prematurely, in the administrative process
    . . . . On the basis of the foregoing, we
    -12-
    dismiss the appeal . . .               for     lack   of
    jurisdiction and as premature.
    Esso, P.R. Court of Appeals, 
    2004 WL 3199104
    , at *5.               It is clear
    that the court denied the motion for interlocutory relief on the
    basis of jurisdiction; there is no discussion of any merits in the
    opinion.   Furthermore, the one-line denial of certiorari by the
    Puerto Rico Supreme Court similarly provides no evidence that it
    contemplated the merits of this case.
    The defendants also urge us to conclude that Esso has
    still failed to demonstrate irreparable harm because there are
    other avenues available, i.e., mandamus relief or initiation of
    state action.      In November 2003, during the course of the EQB
    hearings, Esso filed a motion for expedited recommendation of
    dismissal, alleging constitutional due process claims. At the time
    of this appeal, neither the Hearing Examiner nor the EQB Governing
    Board had ruled on the motion.      The defendants contend that rather
    than   interpret    the   failure   to     act   as   a   denial      and   seek
    interlocutory review by the Puerto Rico Court of Appeals, Esso
    should have filed for mandamus relief to order the agency to rule
    on the motion.
    We expressly discussed a similar scenario in our prior
    opinion.   We noted the possibility that interlocutory relief might
    be precluded by EQB's failure to rule on Esso's motion to dismiss.
    In such an event, we observed that "we might take a different view
    of the applicability of the Gibson exception . . . . However,
    -13-
    general principles of administrative law provide that . . . an
    agency's failure to act on a pending matter is treated as a denial
    of the relief sought."            Esso I, 
    389 F.3d at
    224 n.12 (citing
    Hernández v. Reno, 
    238 F.3d 50
    , 55 (1st Cir. 2001)).                   Likewise, we
    reject   the    defendants'     argument       that    Esso's   failure    to    seek
    mandamus relief precludes review.               Esso's motion to dismiss was
    filed in November 2003 and, four years later, the agency still had
    not issued a decision.        Esso was entitled to treat the failure to
    act as a denial.       See 
    P.R. Laws Ann. tit. 3, § 2173
     (waiving the
    exhaustion      requirement     "when    it     is    useless     to   exhaust   the
    administrative       remedies     due   to     an     excessive    delay   in    the
    procedures").        Furthermore, review of Puerto Rico law does not
    appear to indicate that mandamus is available in a case such as
    this one.    See 
    P.R. Laws Ann. tit. 12, § 1139
     (2004) (recodified as
    P.R. Laws Ann. 12, § 8002m (2007)) (provision allowing mandamus
    relief only to order the EQB to comply with the environmental
    statute); cf. Nieves-Márquez v. Puerto Rico, 
    353 F.3d 108
     (1st Cir.
    2003)    ("It   is   far   from    clear      from    the   defendants'     summary
    presentation, without briefing, that mandamus would be available in
    the Puerto Rico courts to enforce an administrative order.").
    The defendants' argument that Esso should have initiated
    a proceeding in Puerto Rico Superior Court is equally unavailing.
    The underlying principle of the court-made Younger abstention
    doctrine is rooted in a sense of comity and respect for those state
    -14-
    proceedings already in progress.          See, e.g., Rossi v. Gemma, 
    489 F.3d 26
    , 34 (1st Cir. 2007). Indeed, in Maymó-Meléndez, we focused
    the applicability of the Younger doctrine on whether the particular
    proceedings were in fact still "ongoing" during the break between
    trial and appellate review.         
    364 F.3d at 34-35
     (deeming that a
    "proceeding [is] 'ongoing' for Younger purposes until the state
    appellate process [i]s complete" (citing Huffman v. Pursue, Ltd.,
    
    420 U.S. 592
    , 607-11 (1975))).         Thus, Younger precludes a litigant
    in a state administrative proceeding from circumventing review by
    a state court in favor of federal relief.         There is no requirement,
    however, that a litigant file a new, independent claim in state
    court prior to obtaining federal relief.             See Habich v. City of
    Dearborn, 
    331 F.3d 524
    , 531-32 (6th Cir. 2003) ("We are aware of no
    case   in    which   a   federal   plaintiff    is     deemed   to    have    the
    'opportunity' to have his or her federal claim heard in a state
    proceeding solely because the plaintiff could have amended an
    existing complaint or filed a new complaint in state court.").
    Given Esso's failed attempts to obtain interlocutory
    relief in this ongoing administrative proceeding, we conclude that
    Esso has clearly demonstrated the irreparable harm which it will
    suffer in the absence of federal intervention.              Accordingly, we
    conclude that the district court properly found that the need for
    federal     intervention   in   this    case   falls    clearly      within   the
    abstention exception carved out by Gibson.
    -15-
    B.   Bias
    The merits of this case involve allegations that the
    defendants violated Esso's constitutional due process rights as a
    result   of    the   bias    infecting   the   penalty   proceedings.      The
    allegations of bias fall into three categories: (1) the statutory
    structure which provides that the proposed penalty of $76 million
    would go directly into an account administered by the EQB; (2) the
    procedures for the selection of and payment to Hearing Examiners;
    and (3) the prejudice resulting from the Puerto Rico Senate's
    premature conclusion that Esso had violated the environmental
    regulations and the accusation that the EQB had been too lax.              The
    first two allegations raise structural concerns that create the
    appearance of bias in the proceedings; the third allegation raises
    concerns of actual bias.         The district court concluded that the
    defendants had failed to raise any genuine issues of material fact
    as to the appearance of a biased adjudicative process.
    1.    EQB Governing Board
    The EQB is an administrative body comprised of three
    members appointed for a four-year term by the Governor of Puerto
    Rico with the advice and consent of the Puerto Rico Senate.              
    P.R. Laws Ann. tit. 12, § 1129
    (a).             The agency is tasked with the
    responsibility       of     adopting     and   enforcing    Puerto      Rico's
    environmental statutes and regulations, and is empowered to impose
    sanctions and administrative fines on violators, 
    id.
     at § 1136(c),
    -16-
    as   well   as   issue   orders   mandating   the    cessation   of   harmful
    activities, id. at § 1131(22).        Those administrative fines –- the
    crux of this case –- are then deposited into the "Special Account
    of the Board on Environmental Quality."             Id. at § 1136(f), (k);
    § 1131(16)(A) ("All monies received by the [EQB] in the fulfillment
    of its duty to implement [environmental regulations] . . . shall be
    deposited in a special account to be known as the 'Environmental
    Quality Board Special Account.'"). That money is then "place[d] at
    the disposal of the [EQB] . . . through payment orders authorized
    or signed by the Chairperson of the [EQB]."          Id. at § 1131(16)(A).
    Esso asserts that it was denied a fair hearing because of
    the EQB's structural bias.        Specifically, Esso contends that the
    EQB has an institutional interest in imposing hefty fines because
    the collected monies are deposited into an EQB Special Account over
    which the EQB has limitless discretion.          Moreover, in this case,
    the proposed fine –- $76 million -- is more than double the EQB's
    annual budget.     In response, the defendants attempt to focus the
    inquiry on the individual members of the EQB, rather than the
    agency as a whole; the EQB Governing Board members are salaried and
    thus have no personal pecuniary interest in the fines imposed and
    collected by the agency.
    Not only is the defendants' argument utterly unsupported
    by the law, but we have already rejected it.          See Esso I, 
    389 F.3d at 219
    .     On last appeal, we expressly stated,
    -17-
    [T]he adjudicative body stands to
    benefit   financially   from  the   proceeding
    because any fine imposed will flow directly to
    the EQB's budget. Although members of the EQB
    Governing Board may not stand to gain
    personally . . . a pecuniary interest need not
    be personal to compromise an adjudicator's
    neutrality.
    
    Id. at 218-19
    .       Although the law of the case doctrine has been
    refined over time and we have identified several instances in which
    reconsideration of a past decision may be appropriate, see Ellis v.
    United States, 
    313 F.3d 636
    , 647-48 (1st Cir. 2002); this is not
    such an instance.        This court's prior rejection of the defendants'
    argument is neither "unreasonable [n]or obviously wrong."              
    Id.
     at
    648 & n.5.
    Last time, we properly concluded that the bias stems from
    the potential financial benefit to the EQB's budget as a result of
    an imposed fine.         Esso I, 
    389 F.3d at 219
    ; cf. Ward v. Vill. of
    Monroeville, 
    409 U.S. 57
    , 59-60 (1972) (invalidating the mayor's
    court because a substantial portion of the village funds were
    comprised of the fines he imposed for traffic violations).                 In
    Ward,   the    Supreme    Court    expressed   concerns   that   the   funding
    structure would "offer a possible temptation to the average man" to
    the extent that there is a "situation in which an official perforce
    occupies two practically and seriously inconsistent positions, one
    partisan and the other judicial [and] necessarily involves a lack
    of due process of law."           Ward, 
    409 U.S. at 60
     (quoting Tumey v.
    -18-
    Ohio, 
    273 U.S. 510
    , 532, 534 (1927)).           This is not a situation in
    which the EQB Governing Board is so removed from the financial
    policy of the Special Account that such a presumption of bias is
    inapplicable.     Cf. Dugan v. Ohio, 
    277 U.S. 61
     (1928).            Rather, this
    is a case in which the EQB has complete discretion over the usage
    of those funds which are supplied, at least in part, by fines which
    it imposes. In this particular case, the possibility of temptation
    is undeniable and evident in the fact that the size of the proposed
    fine in this case is so unprecedented and extraordinarily large.
    The $76 million proposed fine -- a sum twice the EQB's annual
    operating budget and 5,000 times greater than the largest fine ever
    imposed by the EQB -- only intensifies the appearance of bias
    infecting the proceedings.
    2.   EQB Hearing Examiner
    Hearing Examiners are independent contractors who sign a
    one-year contract for employment with the EQB and are paid a fixed
    hourly rate. They preside over the administrative hearing and make
    recommendations to the Governing Board of the EQB as to whether a
    fine should be levied.       They are assigned cases pursuant to the
    discretion   of    the   EQB;   those       cases   include     administrative
    investigative      proceedings,      quasi-judicial         proceedings,    and
    legislative proceedings.
    The     district   court    concluded      that     the   contractual
    relationship between the EQB and the Hearing Examiners exhibited
    -19-
    structural bias on account of both the method by which the Hearing
    Examiners receive assignments and because of the particularities
    within the pay structure.       We agree.     Hearing Examiners are not
    protected from the pressures of political appointments and their
    employment is entirely dependent on the EQB's willingness to assign
    cases to them.    Furthermore, the evidence on the record indicates
    that the Hearing Examiner's contract in this case provides an
    hourly salary rate with a set maximum number of hours for work.
    Notably, there is no provision for a minimum number of hours.
    Given that a Hearing Examiner's pay is entirely dependent upon the
    discretionary assignment of cases from the EQB, the examiner is
    vulnerable to the temptation to make recommendations favorable to
    the EQB.5
    In addition to the pressure felt by the Hearing Examiners
    with respect to their case assignments from the EQB, we are
    particularly concerned by the evidence that they are paid out of
    the same Special Account into which the fines are deposited.              The
    Hearing Examiner's contract states that "in the eventuality of
    there not existing or being assigned funds for the payment of
    contracted services[,] the contract shall be deemed rescinded
    without any further right to collect."              While there is some
    question    as   to   whether   the     Hearing   Examiner   may   have   an
    5
    Esso asserts that two prior Hearing Examiners were dismissed
    after various disagreements with the EQB regarding the proceedings
    against Esso.
    -20-
    independent, contractual right to challenge a nonpayment of his
    salary by the EQB, it is irrefutable that such a provision -- one
    that expressly links personal salary and the fund into which the
    fines are deposited -- creates the appearance of and an incentive
    for bias.6
    3.   Puerto Rico Senate Report
    The claim of bias is further substantiated by evidence
    that the Puerto Rico Senate improperly exerted pressure on the EQB
    with respect to the assessment of this penalty against       Esso.7
    Specifically, the Puerto Rico Senate Commission on Agriculture,
    Natural Resources, and Energy issued a partial report in which it
    directed the Commission on Government Integrity to "identify those
    public officials [in the EQB] who permitted the slowness with which
    the gasoline spill was dealt with . . . and refer them to both the
    Department of Justice as well as to the Office of Government Ethics
    to determine whether any crime was committed or violation of the
    laws and regulations of the Commonwealth of Puerto Rico."   Partial
    6
    With respect to the Special Account, the defendants contend that
    the account's funds are not supplied solely on the basis of fines,
    but are also funded through the issuance of permits.            The
    defendants argue that this fact severely undercuts the conclusion
    that the hearing examiners are biased. We are unpersuaded. The
    defendants' argument does nothing to alter the funding structure of
    the Special Account nor does it negate the fact that in this case,
    the EQB proposed a fine of $76 million.
    7
    On appeal, the defendants make no challenge to the district
    court's findings regarding the impact of the Puerto Rico Senate
    report on the EQB's proceedings against Esso.
    -21-
    Report on S.R. 1047, at 14 (P.R. Senate July 10, 2003) (certified
    translation). This threat of criminal prosecution of EQB officials
    strongly suggests that the Senate was threatening the EQB and is
    therefore    evidence   of   actual    bias   in   the   proceedings.   See
    Pillsbury Co. v. F.T.C., 
    354 F.2d 952
    , 964 (5th Cir. 1966) (noting
    that a legislative body's "improper intrusion into the adjudicatory
    process" deprives "the right of private litigants to a fair trial
    and, equally important[ly] . . . their right to the appearance of
    impartiality, which cannot be maintained unless those who exercise
    the judicial function are free from powerful external influences"
    (citing In re Murchison, 
    349 U.S. 133
    , 136 (1955))).          The fact that
    the appointment of EQB members requires Senate consent further
    intensifies the incentives felt by the EQB to impose an unduly
    heavy fine on Esso.
    After review of the evidence submitted by the parties, we
    re-affirm our conclusion that there is a strong appearance of bias
    and, additionally, undisputed evidence of actual bias in these
    proceedings.
    C.   Permanent Injunction
    The issuance of a permanent injunction requires the
    application of a familiar four-step framework in which Esso, as the
    plaintiff:
    must demonstrate: (1) that it has suffered an
    irreparable   injury;   (2)   that   remedies
    available at law, such as monetary damages,
    are inadequate to compensate for that injury;
    -22-
    (3) that, considering the balance of the
    hardships between the [parties], a remedy in
    equity is warranted; and (4) that the public
    interest will not be disserved by a permanent
    injunction.
    eBay Inc. v. MercExchange, L.L.C., 
    547 U.S. 388
    , 390 (2006).
    As we have already discussed above, Esso has already
    succeeded   in    demonstrating   that       EQB's   internal   structure   is
    severely biased and that continuation of the proceedings in such a
    fatally biased decisionmaking process violates its due process
    rights.8    Likewise, we have already concluded that Esso faces
    irreparable harm in the absence of injunctive relief given the
    unavailability of avenues for interlocutory relief in the Puerto
    Rico courts.      Thus, we move to the balancing of the harms and the
    inquiry into the public interest.
    The    district   court    issued    the   following   permanent
    injunction:
    It is further ORDERED that the defendants are
    permanently enjoined from conducting any and
    all administrative hearings and proceedings
    against Esso related to the penalty provision
    of the order to show cause . . . . It is
    further ORDERED that the defendants are
    8
    On appeal, the defendants also argue that the court is required
    to inquire into whether the process is still biased, given the
    intervening personnel changes. The defendants concede that this
    argument was not raised below. See Figueroa v. Rivera, 
    147 F.3d 77
    , 81 (1st Cir. 1998) ("[A]ppellants did not raise these
    contentions below, and they are thus foreclosed from unveiling them
    for the first time on appeal."). Moreover, given the allegations
    of structural bias, evidence of personnel substitution is
    insufficient to cure the constitutional infirmity. See Ward, 
    409 U.S. at 61
    .
    -23-
    permanently   enjoined    from   issuing   any
    judgments    or    resolutions,    final    or
    interlocutory, in said matter, and from
    instituting, conducting and/or prosecuting any
    administrative penalty proceedings against
    Esso based on or arising from the facts and
    events described in said order to show cause.
    Esso Standard Oil Co. v. López-Freytes, No. 03-2319 (D.P.R. Nov. 7,
    2006) (order granting permanent injunction).
    In this case, the district court's injunction is tailored
    specifically   to    Esso:   the   injunction    makes     no    mention   of
    administrative actions against other persons or entities and, in
    fact, leaves unhampered the ongoing clean up efforts at the gas
    station itself.     There is little to no harm wrought upon the agency
    or the public.      The injunction takes aim only at the fine to be
    imposed upon Esso.      The defendants do not challenge the narrow
    focus of the injunction itself, but argue that the injunction will
    have a "considerable impact . . . on general compliance with EQB
    environmental law policies in Puerto Rico."              In essence, they
    contend that Esso's success in obtaining an injunction in this case
    will encourage other companies to do the same, and thereby severely
    weaken   the   power    of   the   agency   to   enforce        environmental
    regulations.      They argue that the injunction imposed upon the
    penalty phase in this case has "effectively allowed the release of
    thousands of gallons of gasoline to the environment, potentially
    affecting the health of nearby residents and contaminating the
    -24-
    area's    soil,    as   well   as   its   ground   waters,   to   go   forever
    unpunished."
    We think the defendants grossly exaggerate the impact of
    the injunction and ignore the seriousness of the bias plaguing
    these proceedings.        This case involves evidence that the EQB's
    decisionmaking process with respect to Esso is constitutionally
    infirm.   The serious harm inflicted upon Esso is not outweighed by
    the EQB's concern that this injunction may alter the perceived
    strength of the EQB's governance.            It is clear from the district
    court's thoughtful opinion that the injunction was crafted to
    target the biased penalty proceedings against Esso. The injunction
    specifically exempted the remediation efforts and expressly stated
    that it applied only to the case at hand.            We are unconvinced by
    the defendants assertions, and conclude that the district court did
    not abuse its discretion in issuing a permanent injunction.
    Lastly, the defendants argue that an injunction should
    "be no more burdensome to the defendant than necessary to provide
    complete relief to the plaintiffs." Califano v. Yamasaki, 
    442 U.S. 682
    , 702 (1979).         They also contend that the scope of this
    injunction was overly broad because it lacks an express provision
    for termination of the injunction in the event that the EQB makes
    the required institutional changes to ensure a constitutional
    proceeding.       We are unconvinced by this argument; the defendants
    exaggerate the permanence of the injunction. If the defendants are
    -25-
    able to cure the impermissible sources of bias, they are free to
    move   the    district     court    to   modify       or   dissolve      the    permanent
    injunction.     See Fed. R. Civ. P. 60(b)(5) (providing relief from a
    judgment     order   when    "applying         it   prospectively        is    no    longer
    equitable"); see also Mackin v. City of Boston, 
    969 F.2d 1273
    ,
    1276-77 (1st Cir. 1992) (observing that with respect to those
    "decrees which were initially established to bring about needed
    institutional reforms . . . [the] intrusion by a federal court into
    the affairs of local government should . . . not be allowed to
    continue after the violation has abated and its pernicious effects
    have been cured"). It seems clear that the district court tailored
    an injunction specifically to Esso and in response to the volume of
    evidence      exhibiting      unconstitutional             bias     in    the       penalty
    proceedings against Esso.           The injunction leaves the EQB free to
    continue its important remediation work and to continue pursuing
    claims     against    other    violators.              Upon     evidence        that     the
    constitutional infirmities have been cured, the EQB may move to
    amend the injunction which removes the EQB's concerns that Esso is
    somehow      permanently     beyond      the    reach      of     its    administrative
    oversight.
    III.      Conclusion
    For   the   reasons     stated        above,    the   judgment        of   the
    district court is affirmed.
    Affirmed.
    -26-