Eckert v. Dougherty , 658 F. App'x 401 ( 2016 )


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  •                                                                                 FILED
    United States Court of Appeals
    UNITED STATES COURT OF APPEALS                        Tenth Circuit
    FOR THE TENTH CIRCUIT                      September 14, 2016
    _________________________________
    Elisabeth A. Shumaker
    Clerk of Court
    DAVID ECKERT,
    Plaintiff - Appellant,
    v.                                                        No. 15-2204
    (D.C. No. 2:13-CV-00727-JB-WPL)
    DEPUTY DISTRICT ATTORNEY                                    (D. N.M.)
    DANIEL DOUGHERTY,
    Defendant - Appellee,
    and
    CITY OF DEMING; BOBBY OROSCO;
    ROBERT CHAVEZ; OFFICER
    HERNANDEZ; HIDALGO COUNTY;
    HILDALGO COUNTY SHERIFF
    OFFICERS DAVID ARREDONDO,
    ROBERT RODRIGUEZ, PATRICK
    GREEN; GILA REGIONAL MEDICAL
    CENTER; ROBERT WILCOX, M.D.;
    OKAY ODOCHA, M.D.,
    Defendants.
    _________________________________
    ORDER AND JUDGMENT*
    _________________________________
    Before HARTZ, HOLMES, and McHUGH, Circuit Judges.
    *
    After examining the briefs and appellate record, this panel has determined
    unanimously that oral argument would not materially assist in the determination of
    this appeal. See Fed. R. App. P. 34(a)(2); 10th Cir. R. 34.1(G). The case is therefore
    ordered submitted without oral argument. This order and judgment is not binding
    precedent, except under the doctrines of law of the case, res judicata, and collateral
    estoppel. It may be cited, however, for its persuasive value consistent with
    Fed. R. App. P. 32.1 and 10th Cir. R. 32.1.
    _________________________________
    David Eckert appeals the district court’s judgment in favor of Deputy District
    Attorney Daniel Dougherty in a civil-rights suit under 42 U.S.C. § 1983. Concluding
    that Mr. Dougherty was entitled to qualified immunity, the district court granted his
    motion to dismiss. The court also denied Mr. Eckert’s motion to amend his
    complaint. Exercising jurisdiction under 28 U.S.C. § 1291, we affirm.
    BACKGROUND
    I.    Factual Background
    Because the district court disposed of Mr. Eckert’s claims on a motion to
    dismiss, the facts are taken from Mr. Eckert’s complaint unless otherwise indicated.
    On January 2, 2013, police officer Robert Chavez stopped Mr. Eckert for
    failing to obey a stop sign in Deming, New Mexico. Officer Chavez said that while
    patting Mr. Eckert down, he noticed his “posture to be erect and he kept his legs
    together.” Aplt. App. at 17 (internal quotation marks omitted). Another officer
    arrived and issued Mr. Eckert a citation. Officer Chavez told Mr. Eckert he was free
    to go, but then began questioning him. Officer Chavez decided to search
    Mr. Eckert’s car; it is disputed whether Mr. Eckert consented to the search.
    Hidalgo County Sheriff Deputies David Arredondo and Patrick Green brought
    a “narcotics canine” to search the vehicle. 
    Id. The officers
    reported that the dog
    alerted to the driver’s seat. “[Officer Bobby] Orosco and [Deputy] Arredondo then
    informed [Officer] Chavez that [Mr. Eckert] was known in Hidalgo County to insert
    drugs into his anal cavity.” 
    Id. This information
    was false.
    2
    Officer Chavez contacted Mr. Dougherty about getting a search warrant for
    Mr. Eckert’s vehicle and person. The officer wrote an affidavit in support of the
    warrant stating that the search was “to include but not [be] limited to [Mr. Eckert’s]
    anal cavity.” 
    Id. at 18
    (internal quotation marks omitted). The affidavit primarily
    relied on the following facts to establish probable cause: (1) Mr. Eckert’s posture as
    observed by Officer Chavez (standing erect with his legs together); (2) the dog alert;
    and (3) the statement by the law-enforcement officer(s) (identified in the affidavit
    only as a Hidalgo County K-9 officer) that Mr. Eckert “was known to insert drugs
    into his anal cavity and had been caught in Hidalgo County with drugs in his anal
    cavity.” Dist. Ct. CM/ECF Doc. 26-1 at 2.1 Mr. Dougherty reviewed the affidavit
    and approved it, and a judge signed the search warrant.
    Officer Chavez took Mr. Eckert to the Deming Emergency Room to execute
    the warrant. The attending physician, however, refused to conduct an exam on the
    ground that it was medically unethical. Mr. Dougherty then authorized
    Officer Chavez to transport Mr. Eckert to another medical facility.
    Officer Chavez and an Officer Hernandez took Mr. Eckert to Gila Regional
    Medical Center. A doctor there conducted an abdominal X-ray, which showed no
    foreign object in Mr. Eckert’s rectum or elsewhere in his abdomen.
    Dr. Robert Wilcox then performed a digital rectal exam and reported that he felt
    1
    Although the appellant’s appendix does not include either the warrant
    application or the search warrant, “we have authority to review them because we may
    take judicial notice of public records, including district court filings.” Guttman v.
    Khalsa, 
    669 F.3d 1101
    , 1127 n.5 (10th Cir. 2012).
    3
    something soft that could have been stool. He referred Mr. Eckert to Dr. Okay
    Odocha for a surgical consultation. Dr. Odocha performed a second digital rectal
    exam and detected only stool. Nevertheless, he ordered that Mr. Eckert be
    administered enemas until all results were “clear.” 
    Id. at 20
    (internal quotation marks
    omitted). Mr. Eckert was subjected to three enemas, but his bowel movements
    produced no narcotics. After the third enema, a doctor took a chest X-ray, which also
    revealed no evidence of narcotics. Nevertheless, Dr. Odocha ordered a colonoscopy,
    which was conducted in the early morning of January 3. The colonoscopy also
    revealed no evidence of narcotics.
    II.   Procedural Background
    Mr. Eckert filed a civil-rights complaint against Mr. Dougherty as well as the
    officers and medical personnel. Only the claims against Mr. Dougherty are at issue
    in this appeal. Those claims are based on two actions—the approval of the search
    warrant and affidavit, and the authorization for officers to take Mr. Eckert to Gila
    Regional Medical Center.
    Mr. Dougherty moved to dismiss on the grounds of absolute and qualified
    immunity.2 Mr. Eckert opposed dismissal. After holding a hearing, the district court
    entered a short order granting dismissal. In this order the court found that
    2
    Because immunity is an affirmative defense that Mr. Dougherty raised in his
    answer, this motion, ostensibly made under Rule 12(b)(6), is more accurately
    described as a Rule 12(c) motion for judgment on the pleadings. See Brown v.
    Montoya, 
    662 F.3d 1152
    , 1160 n.4 (10th Cir. 2011). But the error is immaterial
    because this court applies the same standard of review to both Rule 12(c) and Rule
    12(b)(6) motions. See 
    id. 4 prosecutorial
    immunity protected Mr. Dougherty from liability for approving the
    search warrant. The court dismissed the complaint without prejudice to amendment,
    stating, “Plaintiff David Eckert may file a motion for leave to amend the Complaint
    to allege that Dougherty directed police officers to conduct an unlawful search.”
    Aplt. App. at 108.
    Four months later, Mr. Eckert moved to amend his complaint. The proposed
    amended complaint did not seek to add any new theories, and Mr. Eckert conceded
    that he “does not and cannot allege that Dougherty directed the officers to conduct an
    unlawful search.” 
    Id. at 112.
    Instead, the amended complaint presented additional
    factual allegations about a conversation between Mr. Dougherty and the attending
    physician at the Deming Emergency Room that purportedly showed that
    Mr. Dougherty was aware that initial tests could lead to false positives and additional
    (and possibly more invasive) tests. Mr. Eckert represented that he was not aware of
    the details of the conversation before filing his complaint.
    The district court held a hearing on the motion to amend, at which it clarified
    that the basis for its decision had been qualified immunity, not prosecutorial
    immunity.3 It discussed its views of the various issues and denied the motion to
    amend, a decision it soon memorialized in a short written order. The district court
    later issued a comprehensive memorandum opinion discussing its reasons for
    granting the motion to dismiss and denying the motion to amend. In this order it held
    3
    The appellant’s appendix does not include the transcript of this hearing, but
    the district court summarized the proceedings in its memorandum opinion.
    5
    the following: the search warrant affidavit established probable cause; the search
    warrant’s description of the area to be searched was sufficiently particular;
    Mr. Dougherty did not violate Mr. Eckert’s constitutional rights by allowing officers
    to take him to Gila Regional Medical Center; all procedures after the first digital
    exam and the first X-ray were unconstitutional; but Mr. Dougherty neither knew nor
    reasonably should have known that his actions would lead to constitutional
    violations. The district court further held that even if Mr. Dougherty had violated
    Mr. Eckert’s constitutional rights, the law was not clearly established. It denied the
    motion to amend on the grounds that it was untimely and was futile because the
    proposed additional facts failed to show that Mr. Dougherty knew or should have
    known that his actions would cause others to violate Mr. Eckert’s constitutional
    rights. Mr. Eckert appeals both the dismissal and the denial of leave to amend.
    DISCUSSION
    I.    Dismissal
    “This court reviews de novo a district court’s grant of a motion to dismiss
    based on qualified immunity.” Weise v. Casper, 
    593 F.3d 1163
    , 1166 (10th Cir.
    2010). “Once the qualified immunity defense is asserted, the plaintiff bears a heavy
    two-part burden to show, first, the defendant’s actions violated a constitutional or
    statutory right, and, second, that the right was clearly established at the time of the
    conduct at issue.” Thomas v. Kaven, 
    765 F.3d 1183
    , 1194 (10th Cir. 2014) (internal
    quotation marks omitted). A right is clearly established if “a Supreme Court or Tenth
    Circuit decision is on point, or if the clearly established weight of authority from
    6
    other courts shows that the right must be as the plaintiff maintains.” 
    Id. (internal quotation
    marks omitted). “Asserting a qualified immunity defense via a
    Rule 12(b)(6) motion . . . subjects the defendant to a more challenging standard of
    review than would apply on summary judgment,” because “[a]t the motion to dismiss
    stage, it is the defendant’s conduct as alleged in the complaint that is scrutinized for
    objective legal reasonableness.” 
    Id. (alterations and
    internal quotation marks
    omitted). “We may consider the two parts of [the qualified-immunity] test in the
    sequence we deem best in light of the circumstances in the particular case.” Mink v.
    Knox, 
    613 F.3d 995
    , 1000 n.4 (10th Cir. 2010).
    Mr. Eckert does not argue that the district court erred in determining which
    medical procedures were constitutional and which were not; instead, he focuses on
    the alleged insufficiencies in the warrant (so that no procedure performed under the
    warrant was constitutional). Therefore, we do not reexamine whether the district
    court properly concluded that the abdominal X-ray and the first digital exam were
    constitutional and the later procedures were not. Nothing in this decision, however,
    should be read to condone any of the procedures, given the significant privacy
    interests in avoiding forced medical intrusions. See, e.g., Birchfield v. North Dakota,
    
    136 S. Ct. 2160
    , 2176-78 (2016) (blood tests for impaired driving implicate
    significant privacy interests, while breath tests do not).
    Mr. Eckert argues that Mr. Dougherty violated his clearly established Fourth
    Amendment rights (as applicable to the states through the Fourteenth Amendment) by
    (1) approving an unconstitutional search-warrant application, and (2) authorizing the
    7
    officers to continue his detention and to transport him to Gila Regional Medical
    Center.
    A.     Approving the Warrant
    We have held that a prosecutor may be liable for causing the issuance of an
    unconstitutional search warrant. See 
    Mink, 613 F.3d at 1001-03
    . “The requisite
    causal connection is satisfied if the defendant set in motion a series of events that the
    defendant knew or reasonably should have known would cause others to deprive the
    plaintiff of [his] constitutional rights.” 
    Id. at 1001
    (internal quotation marks
    omitted). “The plaintiff may demonstrate causation by showing an affirmative link
    between the constitutional deprivation and the [defendant’s] exercise of control or
    direction.” 
    Id. To be
    constitutional, a search warrant must be issued by a neutral,
    disinterested magistrate; must be based on “probable cause to believe that the
    evidence sought will aid in a particular apprehension or conviction for a particular
    offense”; and “must particularly describe the things to be seized, as well as the place
    to be searched.” 
    Id. at 1003
    (internal quotation marks omitted). Mr. Eckert asserts
    that the search warrant affidavit drafted by Officer Chavez and approved by
    Mr. Dougherty did not adequately establish probable cause and did not particularly
    describe the area to be searched and the methods to be used. He argues that “it is
    foreseeable that approval of a warrant, unsupported by probable cause and unspecific
    as to the location of the place to be searched, will result in a search that violates the
    rights of the subject.” Aplt. Br. at 45.
    8
    1.     Probable Cause
    Mr. Eckert first argues that the affidavit did not establish probable cause.
    “The substance of all the definitions of probable cause is a reasonable ground for
    belief of guilt.” 
    Mink, 613 F.3d at 1003
    (internal quotation marks omitted).
    “Probable cause exists if facts and circumstances within the [official’s] knowledge
    and of which [he] had reasonably trustworthy information are sufficient in
    themselves to warrant a man of reasonable caution in the belief that an offense has
    been or is being committed.” 
    Id. (internal quotation
    marks omitted). “All we have
    required is the kind of fair probability on which reasonable and prudent people, not
    legal technicians, act. In evaluating whether the State has met this practical and
    common-sensical standard, we have consistently looked to the totality of the
    circumstances.” Florida v. Harris, 
    133 S. Ct. 1050
    , 1055 (2013) (brackets, citations,
    and internal quotation marks omitted); see also Illinois v. Gates, 
    462 U.S. 213
    , 230-
    32 (1983) (discussing the totality-of-the-circumstances approach). “In the qualified
    immunity context, we ask whether an objectively reasonable [official] could conclude
    that the historical facts at the time of the arrest amount to probable cause.” Maresca
    v. Bernalillo Cty., 
    804 F.3d 1301
    , 1310 (10th Cir. 2015) (internal quotation marks
    omitted), cert. denied, 
    136 S. Ct. 2509
    (2016); see also 
    Gates, 462 U.S. at 236
    ,
    238-39 (discussing deferential standard of review). We limit our review to that
    question. In other words, in light of clearly established law can we say that
    Mr. Dougherty could not reasonably have concluded that the warrant affidavit
    established probable cause. See Messerschmidt v. Millender, 
    132 S. Ct. 1235
    , 1250
    9
    (2012) (“Even if the warrant in this case were invalid, it was not so obviously lacking
    in probable cause that the officers can be considered ‘plainly incompetent’ for
    concluding otherwise.”); Malley v. Briggs, 
    475 U.S. 335
    , 341 (1986) (“Defendants
    will not be immune if, on an objective basis, it is obvious that no reasonably
    competent officer would have concluded that a warrant should issue; but if officers of
    reasonable competence could disagree on this issue, immunity should be
    recognized.”).
    Mr. Eckert argues that “every fact relied upon in the affidavit is deficient,” and
    that the three primary facts—his posture, the dog alert, and the statement about his
    habits—“amount to nothing more than hunches . . . [that] are worth no more as
    evidence together than they are worth individually.” Aplt. Br. at 38. We disagree
    with Mr. Eckert’s assessment that no reasonable official could conclude that the
    historical facts amount to probable cause. To be sure, as recognized by the district
    court, some of the affidavit’s factual recitations are flawed. As the court also
    recognized, however, the flaws did not eliminate all probative value.
    To begin with, other law-enforcement officers informed Officer Chavez that
    Mr. Eckert “was known to insert drugs into his anal cavity and had been caught in
    Hidalgo County with drugs in his anal cavity.” Dist. Ct. CM/ECF Doc. 26-1 at 2.
    “Police work often requires officers to rely on the observations, statements, and
    conclusions of their fellow officers,” Baptiste v. J.C. Penney Co., 
    147 F.3d 1252
    ,
    1260 (10th Cir. 1998), and “[o]bservations of fellow officers of the Government
    engaged in a common investigation are plainly a reliable basis for a warrant applied
    10
    for by one of their number,” United States v. Ventresca, 
    380 U.S. 102
    , 111 (1965);
    see Foote v. Spiegel, 
    118 F.3d 1416
    , 1424 (10th Cir. 1997) (“Officers may rely on
    information furnished by other law enforcement officials to establish reasonable
    suspicion and probable cause for an arrest.”). “[A] police officer who acts in reliance
    on what proves to be the flawed conclusions of a fellow police officer may
    nonetheless be entitled to qualified immunity as long as the officer’s reliance was
    objectively reasonable.” 
    Baptiste, 147 F.3d at 1260
    (internal quotation marks
    omitted). Officer Chavez could reasonably rely on the information about Mr. Eckert
    from a fellow officer. It is not necessary that the other officer be named; it is enough
    that he was identified as an “Hidalgo County K-9 Officer,” Dist. Ct. CM/ECF Doc.
    26-1 at 2.
    In that light, the officer’s evaluation of Mr. Eckert’s posture is significant. “A
    magistrate is entitled to rely on the expert opinions of officers when supporting
    factual information is supplied in the affidavit.” United States v. Cook, 
    949 F.2d 289
    ,
    292-93 (10th Cir. 1991); see also United States v. Corral-Corral, 
    899 F.2d 927
    , 937
    (10th Cir. 1990) (“Courts frequently have relied on the expert opinion of officers in
    determining where contraband might be kept.”). And even though we doubt that the
    dog’s alert alone could suffice if it were not shown that the dog was a certified drug
    dog, see 
    Harris, 133 S. Ct. at 1057
    (“If a bona fide organization has certified a dog
    after testing his reliability in a controlled setting, a court can presume (subject to any
    conflicting evidence offered) that the dog’s alert provides probable cause to
    search.”); United States v. Kennedy, 
    131 F.3d 1371
    , 1376-77 (10th Cir. 1997) (“[A]
    11
    search warrant based on a narcotics canine alert will be sufficient on its face if the
    affidavit states that the dog is trained and certified to detect narcotics.”), Mr. Eckert
    has not cited any binding authority requiring the court to ignore the suggestiveness of
    the alert by what the complaint describes as a “narcotics canine.” Aplt. App. at 17.
    “[C]ourts may not engage in a ‘divide-and-conquer’ analysis of facts to
    determine whether probable cause existed.” United States v. Valenzuela, 
    365 F.3d 892
    , 897 (10th Cir. 2004). Although this is a close question, an objectively
    reasonable official could have concluded that the facts at the time of the request for
    the search warrant, combined with the reasonable inferences to be drawn therefrom,
    amounted to probable cause. Accordingly, Mr. Dougherty is entitled to qualified
    immunity on this portion of the claim. See 
    Messerschmidt, 132 S. Ct. at 1250
    ;
    
    Malley, 475 U.S. at 341
    .
    2.     Particular Description
    Mr. Eckert also argues that the warrant insufficiently described the place to be
    searched and the manner in which the search was to be conducted. “[P]ractical
    accuracy rather than technical precision controls the determination of whether a
    search warrant adequately describes the premises to be searched. Therefore, a
    warrant description is sufficient if it enables the officers to ascertain the place to be
    searched with reasonable effort.” United States v. Occhipinti, 
    998 F.2d 791
    , 799
    (10th Cir. 1993) (citation and internal quotation marks omitted). As with our
    probable-cause analysis, the issue is not whether the warrant was sufficiently
    particular, but whether in light of clearly established law, every reasonable official
    12
    would have recognized that it was not sufficiently particular. See 
    Messerschmidt, 132 S. Ct. at 1250
    ; 
    Malley, 475 U.S. at 341
    .
    The warrant authorized the search of Mr. Eckert’s “person . . . , to include but
    not limited to his anal cavity.” Dist. Ct. CM/ECF Doc. 26-1 at 1. Mr. Eckert
    complains that the warrant authorized the search of his entire body and that even the
    specific reference to his “anal cavity” is too vague because “‘[a]nal cavity’ is not a
    term used in medicine and simply refers to what the anus is – an opening.” Aplt. Br.
    at 40.
    In addressing the overbreadth of a search warrant, this court has held with
    respect to computer searches that the text of the warrant should be read “with due
    regard to context, coupled with the specifics of the supporting affidavit.” United
    States v. Burgess, 
    576 F.3d 1078
    , 1092 (10th Cir. 2009). In United States v. Brooks,
    
    427 F.3d 1246
    , 1252 (10th Cir. 2005), for example, we recognized that “the language
    of the warrant may, on first glance, authorize a broad, unchanneled search through
    Brooks’s document files.” But, we continued, “as a whole, [the warrant’s] language
    more naturally instructs officers to search those files only for evidence related to
    child pornography. In this light, the warrant should be—and was—read by officers to
    implicitly place the same restriction (i.e., to locate child pornography) on the scope
    of the entire search.” 
    Id. The Eighth
    Circuit has considered similar reasoning in a context analogous to
    the circumstances before us. In United States v. Nelson, 
    36 F.3d 758
    , 759 (8th Cir.
    1994), officers subjected the defendant to several medical procedures, including an
    13
    endoscopy, under the authority of a warrant to search the defendant’s “person.” The
    court held that “the search warrant for appellant’s ‘person’ was not sufficient to
    authorize a body cavity search.” 
    Id. at 760.
    The court further considered, however,
    whether the affidavit, which purportedly requested permission for a body-cavity
    search, could cure the warrant. See 
    id. In those
    circumstances the court held that it
    could not, because it was not incorporated into the warrant by reference. See 
    id. And the
    court went on to note that “even if . . . the officers could have reasonably believed
    that the warrant included authorization for a body cavity search, . . . the endoscopy
    exceeded the scope of what any reasonable police officer would believe to be
    authorized by the search warrant.” 
    Id. at 761.
    Although the warrant here authorized a search of Mr. Eckert’s “person,” it
    went beyond that general reference to identify Mr. Eckert’s “anal cavity.” Dist. Ct.
    CM/ECF Doc. 26-1 at 1. And unlike in Nelson, the supporting affidavit, which also
    discussed the “anal cavity,” was incorporated into the warrant. See Dist. Ct.
    CM/ECF Doc. 26-2 at 1. That affidavit made it clear that officers suspected
    Mr. Eckert was hiding drugs in his rectal area. The term “anal cavity” may not be
    medically accurate, but we must “interpret search warrant affidavits in a common
    sense and realistic fashion,” 
    Burgess, 576 F.3d at 1091
    (internal quotation marks
    omitted). In layman’s terms, the “anal cavity” corresponds to an area reasonably
    associated with the rectum and colon. It is evident from the context that the warrant
    should not be read to allow medical searches of all portions of Mr. Eckert’s body, but
    instead must be read to focus on his rectal area. A reasonable official reading in
    14
    context and using common sense thus would not necessarily consider the warrant to
    be overbroad.
    Relying on United States v. Gray, 
    669 F.3d 556
    , 566 (5th Cir.), vacated and
    remanded on other grounds, 
    133 S. Ct. 151
    (2012), and United States v. Cameron,
    
    538 F.2d 254
    , 259 (9th Cir. 1976), Mr. Eckert also argues that the search warrant
    affidavit was insufficiently particular regarding the means of conducting the search.
    In Gray, which involved a warrant authorizing a body-cavity search for drugs “in
    accordance with recognized accepted medical 
    procedure,” 669 F.3d at 560
    (internal
    quotation marks omitted), the court “urge[d] warrant-issuing magistrates to cabin the
    search warrant more than the ‘recognized medical procedure’ language in this
    warrant,” 
    id. at 566.
    And in Cameron, in discussing the desirability of a search
    warrant for body-cavity searches, the Ninth Circuit noted that “[t]he warrant defines
    the scope of the search, so that the suspect will know what procedures he 
    faces.” 538 F.2d at 259
    .
    But neither Gray nor Cameron necessarily would cause a reasonable official in
    Mr. Dougherty’s position to recognize that the warrant was insufficiently particular
    for failing to describe any medical procedures. Because these decisions are not
    Supreme Court or Tenth Circuit cases, they are not controlling in this circuit, and
    Mr. Eckert has not identified any Supreme Court or Tenth Circuit authority requiring
    a description of authorized medical procedures. Cf. 
    Brooks, 427 F.3d at 1252
    (search
    warrant for computer “need not have included a search protocol to satisfy the
    particularity requirement of the Fourth Amendment”). Further, the portions of Gray
    15
    and Cameron that Mr. Eckert relies on are dicta, not holdings. Gray “urge[s]” a
    course of 
    action, 669 F.3d at 566
    , and Cameron merely comments on a benefit of a
    warrant in circumstances that were not before the court, 
    see 538 F.2d at 259
    .
    For these reasons, a reasonable official in Mr. Dougherty’s position could fail
    to perceive any problem with the warrant’s specificity, entitling Mr. Dougherty to
    qualified immunity. See 
    Messerschmidt, 132 S. Ct. at 1250
    ; 
    Malley, 475 U.S. at 341
    .
    B.     Authorizing the Transfer
    Mr. Eckert also argues that Mr. Dougherty violated his rights by participating
    in and enabling his unlawful arrest without probable cause when Mr. Dougherty
    authorized the officers to continue to detain him for transport to Gila Regional
    Medical Center. As discussed above, however, a reasonable official could believe
    that probable cause existed. The question then is whether, in light of the warrant’s
    issuance, it would be obvious to any reasonable official that it would be clearly
    unlawful for officers to detain Mr. Eckert for a reasonable time to execute the
    warrant. Mr. Eckert has not cited any cases establishing this proposition, and our
    research has not located any. Mr. Eckert therefore has failed to show that the law
    was clearly established, see 
    Thomas, 765 F.3d at 1194
    , and Mr. Dougherty is entitled
    to qualified immunity on this claim.
    True, Mr. Eckert’s detention extended beyond the period reasonably necessary
    to perform the constitutional portions of the search, when he was subjected to what
    we assume to have been unconstitutional procedures. But Mr. Dougherty cannot be
    liable for that extended detention because (1) Mr. Eckert conceded that he “does not
    16
    and cannot allege that Dougherty directed the officers to conduct an unlawful
    search,” Aplt. App. at 112, and (2) as the district court held, it was not reasonably
    foreseeable to Mr. Dougherty that Mr. Eckert would be subjected to unconstitutional
    procedures (and the concomitant delay) after the initial negative test results.
    II.   Motion to Amend
    Mr. Eckert also challenges the district court’s refusal to allow him to amend
    his complaint. The district court held that the motion was unduly delayed and
    amendment would be futile. We review a denial of amendment for abuse of
    discretion, except that “[w]here the reason for denial of leave to amend is futility, we
    review de novo the legal basis for the finding of futility.” Jones v. Norton, 
    809 F.3d 564
    , 579 (10th Cir. 2015), petition for cert. filed (U.S. July 13, 2016) (No. 16-72).
    Under Fed. R. Civ. P. 15(a)(2), “[t]he court should freely give leave [to
    amend] when justice so requires.” But “[i]t is well settled in this circuit that
    untimeliness alone is a sufficient reason to deny leave to amend, especially when the
    party filing the motion has no adequate explanation for the delay.” Frank v. U.S.
    West, Inc., 
    3 F.3d 1357
    , 1365-66 (10th Cir. 1993) (citations omitted); see also State
    Distribs., Inc. v. Glenmore Distilleries Co., 
    738 F.2d 405
    , 416 (10th Cir. 1984)
    (“Where the party seeking amendment knows or should have known of the facts upon
    which the proposed amendment is based but fails to include them in the original
    complaint, the motion to amend is subject to denial.”). Mr. Eckert filed his motion to
    amend almost 18 months after he filed his original complaint, and four months after
    the court granted the motion to dismiss while giving him leave to amend to assert that
    17
    Mr. Dougherty had directed the officers to conduct an illegal search. The amended
    complaint did not allege any new legal theories, but instead added detail about a
    conversation between Mr. Dougherty and the physician at the Deming Emergency
    Room, who allegedly told Mr. Dougherty that the planned search could result in
    further testing. Although the motion asserted that “Eckert was not aware of the
    details of the conversation between [the physician] and Dougherty prior to filing the
    complaint,” Aplt. App. at 113, there was no explanation why the motion could not
    have been filed earlier. In fact, Mr. Eckert discussed the doctor’s views in his
    response to Mr. Dougherty’s motion to dismiss, a year before he filed the motion to
    amend. Given both the length of time between the original complaint and the motion
    to amend and Mr. Eckert’s failure to explain why he should not have known the
    details of the conversation either at the time of filing or some time reasonably soon
    thereafter, the district court did not abuse its discretion in denying amendment on the
    ground of undue delay.
    The district court also concluded that the proposed amendment was futile,
    another ground for denying amendment, see 
    Frank, 3 F.3d at 1365
    . Mr. Eckert
    argues that “the additional facts alleged in [his] proposed amended complaint state
    that Dougherty was aware that the search authorized in the warrant may have led to
    the discovery of something incidental in the initial digital rectal exam that would
    result in a series of further, and possibly more invasive testing.” Aplt. Br. at 53. But
    as the district court recognized, even in light of the conversation,
    18
    [i]t was not reasonably foreseeable . . . that police and physicians at the
    second hospital would administer a chest X-ray, three enemas, or a
    colonoscopy. Dougherty, a medical layman, neither knew nor should have
    known that his actions would lead to such severe consequences, and no jury
    could reasonably infer that he should have known.
    Aplt. App. at 259.
    CONCLUSION
    The district court’s judgment is affirmed.
    Entered for the Court
    Harris L Hartz
    Circuit Judge
    19