Court Opinion

ID: 6347625
Source: CourtListenerOpinion
Date Created: 2022-06-07 17:00:38.31189+00
Date Added: 2024-06-11T14:21:35.907554
License: Public Domain

Appellate Case: 21-6054    Document: 010110693722   Date Filed: 06/07/2022   Page: 1
                                                          FILED
                                              United States Court of Appeals
                   UNITED STATES COURT OF APPEALS     Tenth Circuit

                            FOR THE TENTH CIRCUIT                   June 7, 2022
                          _________________________________
                                                               Christopher M. Wolpert
                                                                   Clerk of Court
  JOSEPH P. SEAY, D.D.S., M.S.;
  LOIS JACOBS, D.D.S., M.S.,

         Plaintiffs - Appellants,
                                                      No. 21-6054
  v.                                           (D.C. No. 5:17-CV-00682-D)
                                                      (W.D. Okla.)
  OKLAHOMA BOARD OF
  DENTISTRY; SUSAN ROGERS,
  individually and Executive Director
  of the Oklahoma Board of Dentistry;
  JAMES A. SPARKS, D.D.S.,
  individually and President of
  District 5 of the Oklahoma Board of
  Dentistry; AUDREY CRAWFORD,
  D.D.S., individually and District 8
  Board Member of the Oklahoma
  Board of Dentistry; CURTIS
  BOWMAN, D.D.S., individually and
  District 1 Board Member of the
  Oklahoma Board of Dentistry;
  JOSEPH DARROW, D.D.S., District
  6 Board Member of the Oklahoma
  Board of Dentistry; PHIL COTTON,
  Chief, Public Member of the
  Oklahoma Board of Dentistry;
  ANGELA CRAIG, R.D.H., Hygiene
  Member of the Oklahoma Board of
  Dentistry; JAMES GORE, D.D.S.,
  individually and District 7 Board
  Member of the Oklahoma Board of
  Dentistry; MICHAEL HOWL,
  D.D.S., individually and 1st Vice
  President of District 2 of the
  Oklahoma Board of Dentistry; LISA
  NOWLIN, D.D.S., individually and
  District 3 Board Member of the
  Oklahoma Board of Dentistry; LORI
Appellate Case: 21-6054   Document: 010110693722    Date Filed: 06/07/2022   Page: 2

     ROBERTS, Esq., Public Board
     Member of the Oklahoma Board of
     Dentistry; JEFF LUNDAY, D.D.S.,
     individually and 2nd Vice President
     of the Oklahoma Board of Dentistry,

           Defendants - Appellees.
                       _________________________________

                    AMENDED ORDER AND JUDGMENT *
                      _________________________________

 Before HOLMES, BALDOCK, and BACHARACH, Circuit Judges.
                 _________________________________

         This case involves the scope of a state board’s authority to grant a

 specialty license. The Plaintiffs are two dental anesthesiologists, Joseph

 Seay and Lois Jacobs, who have sought specialty licenses from the

 Oklahoma Board of Dentistry. Dr. Seay and Dr. Jacobs wanted to use these

 licenses in advertisements, but until recently Oklahoma law did not allow

 specialty licenses in dental anesthesiology. So the Board allegedly deemed

 Dr. Seay and Dr. Jacobs ineligible for specialty licenses.

         Dr. Seay and Dr. Jacobs responded by suing the Board and its

 members for violating the Constitution and antitrust laws. For these

 claims, Dr. Seay and Dr. Jacobs sought a declaration invalidating the

 Oklahoma law and a related Board rule, an injunction prohibiting

 *
       This order and judgment does not constitute binding precedent except
 under the doctrines of law of the case, res judicata, and collateral estoppel.
 But the order and judgment may be cited for its persuasive value if
 otherwise appropriate. Fed. R. App. P. 32.1(a); 10th Cir. R. 32.1(A).
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 enforcement of the state law and the Board rule, and compensatory

 damages against the Board members in their individual capacities. The

 Board members moved for summary judgment based on timeliness,

 qualified immunity, and statutory limitations on the Board’s authority to

 issue the specialty licenses. The federal district court granted summary

 judgment to the Board members based on timeliness.

       But the Oklahoma law changed in May 2021 to recognize dental

 anesthesiology as a specialty, and the Board has represented that it will

 grant specialty licenses to the Plaintiffs when they complete new

 applications. The Board’s representations moot the Plaintiffs’ claims for

 declaratory and injunctive relief.

       Though these claims became moot, Dr. Seay and Dr. Jacobs had also

 sought damages for violations of the antitrust laws and the Constitution.

 On these claims for damages, we affirm the grant of summary judgment.

       On the antitrust claim, Dr. Seay and Dr. Jacobs haven’t addressed the

 district court’s reasoning, so they’ve waived their challenge to the

 summary-judgment ruling.

       On the constitutional claims for damages, the Defendants argue not

 only that the claims were untimely but also that the Board members

 couldn’t change or subvert Oklahoma law’s restrictions on specialty

 licenses. Dr. Seay and Dr. Jacobs could have addressed this argument in

 their reply brief, but they didn’t. As a result, they waived any nonobvious

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 defect in the Defendants’ alternative argument for affirmance. We see no

 obvious defect in that argument, so we also affirm the award of summary

 judgment on the constitutional claims for damages.

 I.    Our review is de novo.

       We conduct de novo review of the district court’s grant of summary

 judgment. Murphy v. City of Tulsa, 950 F.3d 641, 643 (10th Cir. 2019). In

 conducting this review, we consider the evidence in the light most

 favorable to Dr. Seay and Dr. Jacobs, affirming only if no genuine dispute

 of material fact exists and the Defendants are entitled to judgment as a

 matter of law. Fed. R. Civ. P. 56; Simpson v. Univ. of Colo. Boulder, 500

 F.3d 1170, 1173 (10th Cir. 2007).

 II.   The claims for prospective relief became prudentially moot when
       the law changed and the Board softened its position.

       Dr. Seay and Dr. Jacobs seek injunctive and declaratory relief to

 require issuance of specialty licenses in dental anesthesiology. When the

 Plaintiffs sued, the specialty licenses were not permitted under Oklahoma

 law. But during the pendency of the appeal, the Oklahoma legislature

 amended the Oklahoma Dental Act to include “dental anesthesiology” as a

 recognized specialty. Okla. Stat. tit. 59, § 328.22(A)(3)(j) (2021 supp.).

       The Plaintiffs argue on appeal that the statutory change won’t help

 them for two reasons:

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       1.     Dr. Seay and Dr. Jacobs had received their master’s degrees in
              anesthesiology before the Commission on Dental Accreditation
              began accrediting anesthesiology schools.

       2.     The Board and its members previously represented that Dr.
              Seay and Dr. Jacobs would never obtain eligibility for specialty
              licenses because they had obtained their master’s degrees
              before their schools obtained accreditation.

 Plaintiffs’ Opening Br. at 9. In support, the Plaintiffs cite a brief that the

 Defendants had filed about 1½ years before the statutory change. Id.

 (citing Appellants’ App’x vol. 4, at 607–09).

       But the Board relaxed its position after the law had changed. At oral

 argument and in supplemental briefing, the Board has represented that it

 will grant specialty licenses to Dr. Seay and Dr. Jacobs once they complete

 new applications. Given these representations, the claims for declaratory

 and injunctive relief became prudentially moot.

       A.     The claims for declaratory and injunctive relief are
              prudentially moot.

       Claims become moot “when the issues presented are no longer ‘live’

 or the parties lack a legally cognizable interest in the outcome.” Already,

 LLC v. Nike, Inc., 568 U.S. 85, 91 (2013) (quoting Murphy v. Hunt, 455

 U.S. 478, 481 (1982) (per curiam)). Mootness encompasses both

 constitutional requirements and prudential considerations. See Jordan v.

 Sosa, 654 F.3d 1012, 1023 (10th Cir. 2011).

       Even if a claim is not constitutionally moot, a court can decline to

 consider requests for declaratory or injunctive relief when the claims

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 become prudentially moot. 1 Jordan v. Sosa, 654 F.3d 1012, 1023–24 (10th

 Cir. 2011). We consider a claim prudentially moot if the dispute is

 sufficiently “attenuated that considerations of prudence and comity for

 coordinate branches of government counsel the court to stay its hand, and

 to withhold relief it has the power to grant.” Fletcher v. United States, 116

 F.3d 1315, 1321 (10th Cir. 1997) (quoting Bldg. & Constr. Dep’t v.

 Rockwell Int’l Corp., 7 F.3d 1487, 1491–92 (10th Cir. 1993)); see also S.

 Utah Wilderness All. v. Smith, 110 F.3d 724, 727 (10th Cir. 1997)

 (“Prudential mootness addresses ‘not the power to grant relief but the

 court’s discretion in the exercise of that power.’” (quoting Chamber of

 Com. v. U.S. Dep’t of Energy, 627 F.2d 289, 291 (D.C. Cir. 1980))).

       The prospective claims became prudentially moot when

             the state legislature modified the law by recognizing dental
              anesthesiology as a specialty and

             the Board softened its position on the Plaintiffs’ eligibility for
              specialty licenses.

 1
       We need not address constitutional mootness before prudential
 mootness. See Sinochem Int’l Co. v. Malaysia Int’l Shipping Corp., 549
 U.S. 422, 431 (2007) (“[A] federal court has leeway ‘to choose among
 threshold grounds for denying audience to a case on the merits.’” (quoting
 Ruhrgas AG v. Marathon Oil Co., 526 U.S. 574, 585 (1999))); see also
 Charles Allen Wright, Arthur R. Miller, and Edward H. Cooper, 13B Fed.
 Prac. & Proc. Juris. § 3533.1, at 763 (3d ed. 2008) (“It also is appropriate
 to invoke a prudential principle without confronting the uncertain line
 between Article III and prudential grounds . . . .”).
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       Despite the change in state law and the Board’s softening of its

 position, the Plaintiffs argue that the Board hasn’t amended its rules to

 recognize dental anesthesiology as a specialty. Regardless of whether the

 rules changed, 2 the Board has acknowledged the statutory change and

 recognized the Plaintiffs’ eligibility for specialty licenses. For example, in

 oral argument, the Board represented that it would grant the specialty

 licenses. Oral Argument at 17:15–17:30; 20:15–20:34. The Board later

 confirmed in writing that it would “grant the specialty license[s] once the

 requirements are met.” Appellees’ Supp. Resp. Br. on Mootness at 2.

       Despite these representations, the Plaintiffs point out that they still

 haven’t obtained their specialty licenses. But the licenses are available

 upon the Plaintiffs’ completion of new applications.

       Dr. Seay applied in 2017 when state law prohibited specialty

 licenses. Though the Board stated that Dr. Seay just needed to reapply, he

 hasn’t done that. Appellees’ Supp. Resp. Br. on Mootness at 2.

       Unlike Dr. Seay, Dr. Jacobs applied after Oklahoma had amended the

 statute. 3 Days after she had applied, the Board told her that she needed to

 submit a copy of her driver’s license, passport, or birth certificate.

 2
      At oral argument, the Board asserted that it had changed its rules.
 But we need not address this assertion.
 3
       Dr. Jacobs had previously applied for a specialty license in dental
 anesthesiology in 2019, but she withdrew her application two days later.
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       Dr. Jacobs hasn’t provided the required copy in the 8+ months that

 have passed. The Board nonetheless approved Dr. Jacobs for a specialty

 license and told her that she would get the license once she furnishes a

 copy of her driver’s license, passport, or birth certificate. The Board then

 informed us that it will “grant the specialty license once the requirements

 are met.” Appellees’ Supp. Resp. Br. on Mootness at 2.

       The Plaintiffs argue that the Board’s representations do not moot

 their claims because

             they do not know “what the additional requirements might be,”
              Appellants’ Am. Supp. Br. on Mootness at 4, and

             the Board already has the information needed for the specialty
              licenses, Appellants’ Supp. Reply Br. on Mootness at 5.

 But the Board told Dr. Jacobs what the additional requirements were in

 emails in August, September, and November 2021. So Dr. Jacobs should

 know the additional requirements. And the Board’s application form

 clearly states the requirements, which include proof of citizenship (a birth

 certificate or passport). 4 So the requirements are apparent from the

 application form.

       Regardless of whether the Board already has the necessary

 documentation, the claims for prospective relief remain prudentially moot.

 4
       Okla. Bd. of Dentistry, Dentist/Specialty/Hygienist Application by
 Credentials, available at
 https://www.ok.gov/dentistry/documents/App%20by%20cred%20adv%20pr
 oc%202-3-2020.pdf (last visited Mar. 15, 2022).
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 The Board has unequivocally represented—both in oral argument and in

 supplemental briefing—that it will grant specialty licenses to Dr. Seay and

 Dr. Jacobs upon completion of new applications.

         In these circumstances, declaratory or injunctive relief would do

 little beyond what the legislature and the Board have already done. Once

 Dr. Seay completes a new application and Dr. Jacobs provides a copy of

 her identification, they will receive specialty licenses with or without

 judicial action. The claims for prospective relief are thus prudentially

 moot.

         B.   The exception for voluntary cessation does not apply.

         The Plaintiffs argue that even if the claims were otherwise moot, an

 exception would apply for the Board’s voluntary cessation of the allegedly

 wrongful conduct. See Friends of the Earth, Inc. v. Laidlaw Env’t Servs.

 (TOC), Inc., 528 U.S. 167, 174, 190 (2000) (stating that a defendant’s

 voluntary cessation of allegedly unlawful conduct does not render the

 dispute moot if the conduct could “reasonably be expected to recur”); see

 also Rio Grande Silvery Minnow v. Bureau of Reclamation, 601 F.3d 1096,

 1122 (10th Cir. 2010) (stating that an exception for voluntary cessation can

 apply to both constitutional and prudential mootness). Invoking this

 exception, the Plaintiffs argue that the Board could still deny the

 applications for specialty licenses. We reject this argument.

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        When a claimant challenges a regulation, an amendment ordinarily

  moots the dispute. Rio Grande Silvery Minnow, 601 F.3d at 1116. “But a

  case is not moot if a challenged regulation is repealed and there are ‘clear

  showings of reluctant submission [by government actors] and a desire to

  return to the old ways.’” Citizen Ctr. v. Gessler, 770 F.3d 900, 908 (10th

  Cir. 2014) (quoting Rio Grande Silvery Minnow, 601 F.3d at 1117)

  (alteration in original). So we must consider whether the Board has shown

  a willingness to deny the applications even after representing that it will

  grant the specialty licenses. In our view, the Plaintiffs lack a reasonable

  basis for their apprehension.

        The Board told the Plaintiffs and our court that Dr. Jacobs needed

  only to submit a copy of her identification. Months passed without

  compliance, and the Board reminded Dr. Jacobs—this time, stating that it

  would mail her the specialty license as soon as she furnished a copy of her

  identification. Then the Board told us of these communications and

  represented that it would issue Dr. Jacobs a specialty license once she

  supplies a copy of her identification. We lack any reason to question the

  Board’s willingness to fulfill its representations to Dr. Jacobs and to us.

        The Board made similar representations regarding Dr. Seay, stating

  that he would obtain a specialty license once he completes a new

  application. Despite this representation, Dr. Seay hasn’t submitted a new

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  application. We again lack any reason to question the Board’s willingness

  to carry out its representation by granting Dr. Seay a specialty license.

         The exception for voluntary cessation does not apply, and the claims

  for prospective relief became prudentially moot when the Board

  represented that it would furnish the specialty licenses to Dr. Jacobs and

  Dr. Seay.

  III.   The Plaintiffs’ claims for damages are invalid.

         Though the claims for damages aren’t moot, they’re invalid. The

  Plaintiffs waived an appellate challenge to the antitrust claim for damages,

  and the constitutional claims for damages fail because the Board couldn’t

  grant the specialty licenses until the law changed.

         A.   The Plaintiffs waived their appellate argument on the
              antitrust claim.

         The Plaintiffs claimed a violation of the antitrust laws and argued in

  district court that their suit had been timely based on a continuing

  conspiracy to restrain the Plaintiffs from practicing their trade. The district

  court rejected this argument and dismissed the antitrust claim as untimely.

         On appeal, the Plaintiffs have not reasserted a continuing conspiracy.

  They instead argue that

             their “right to compete is still being suppressed” and

             the district court rejected “the importance of Plaintiffs’ right to
              speech and to competition.”

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  Appellants’ Opening Br. at 20. But these arguments don’t bear on the

  existence of a continuing conspiracy. So even if we were to credit the

  Plaintiffs’ arguments, they wouldn’t undermine the district court’s reason

  for granting summary judgment on the antitrust claim. By failing to

  challenge the district court’s reasoning on this claim, the Plaintiffs waived

  this appellate issue. See Navajo Nat. v. San Juan Cnty., 929 F.3d 1270,

  1281 (10th Cir. 2019) (stating that an argument was waived when the

  appellant hadn’t explained “why the district court was wrong” (quoting

  Nixon v. City & Cnty. of Denver, 784 F.3d 1364, 1366 (10th Cir. 2015))).

        B.    The Plaintiffs also waived any non-obvious defect in the
              Board members’ argument to affirm on alternative grounds.

        The district court regarded the constitutional claims as untimely, and

  the Plaintiffs confined their appellate argument to the issue of timeliness.

  But we need not address timeliness because we affirm on alternative

  grounds.

        In their appellate response brief, the Board members urged us to

  affirm based not only on timeliness but also on the prior statutory

  restrictions on specialty licenses. The Plaintiffs filed a reply brief, but

  didn’t address the Board members’ reliance on the prior statutory

  restrictions. Through that omission, the Plaintiffs waived any non-obvious

  defect in the Board members’ alternative argument for affirmance, and we

  see no obvious defect.

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        1.    We can affirm the award of summary judgment on
              alternative grounds.

        We have “discretion to affirm on any ground adequately supported by

  the record.” Elkins v. Comfort, 392 F.3d 1159, 1162 (10th Cir. 2004). In

  deciding how to exercise our discretion, we consider whether

             “the ground was fully briefed and argued here and below,”

             “the parties have had a fair opportunity to develop the factual
              record,” and

             “our decision would only involve questions of law” “in light of
              factual findings to which we defer or uncontested facts.”

  Elkins v. Comfort, 392 F.3d 1159, 1162 (10th Cir. 2004) (citations &

  internal quotation marks omitted). Each factor supports consideration of

  the Board’s argument for affirmance on the alternative ground that the

  Board previously lacked statutory authority to issue the licenses.

        First, the Defendants briefed the issue in district court and on appeal.

  The Plaintiffs could have (and should have) responded to this alternative

  argument for affirmance. But they didn’t.

        Second, both parties had a fair opportunity to develop the factual

  record on the Board’s authority to grant a specialty license. In district

  court, the Defendants moved for summary judgment on this issue,

  triggering an obligation for Dr. Seay and Dr. Jacobs to present their

  evidence on the Board’s authority to grant a specialty license. See Celotex

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  v. Catrett, 477 U.S. 317, 325 (1986). So we have a full factual record to

  decide the issue.

        Finally, the Board’s authority involves a purely legal question. Even

  now, the parties present no factual disputes as to the Board’s authority

  prior to the recent statutory change.

        Because each factor supports consideration, we address the

  Defendants’ argument for affirmance on alternate grounds involving the

  Board’s prior inability to grant the specialty licenses.

        2.    The Plaintiffs waived their opportunity to address the
              statutory constraints on the Board.

        In their response brief, the Board members argued that the claims for

  damages were invalid because

             Oklahoma law previously did not recognize dental
              anesthesiology as a specialty,

             the Board was just carrying out the state law, and

             the Board couldn’t have done anything differently.

  Appellees’ Resp. Br. at 7–8. In their reply brief, the Plaintiffs did not

  respond to the merits of the Board members’ argument. The Plaintiffs

  instead argued that

             the issue didn’t relate to the district court’s rationale,

             the Board members’ brief did not refer to the record, and

             the argument was not responsive to the opening brief.

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  Appellants’ Reply Br. at 4. Missing, however, was a response to the

  substance of the Board members’ argument.

        We don’t craft arguments for the parties. Perry v. Woodward, 199

  F.3d 1126, 1141 n. 13 (10th Cir. 1999). The Board members urged

  affirmance on alternative grounds, and the Plaintiffs had a full opportunity

  to address that argument in their reply brief. They declined to do so. By

  forgoing a response in their reply brief, the Plaintiffs waived any non-

  obvious defect in the Board members’ alternative argument for affirmance.

  Hasan v. AIG Prop. Cas. Co., 935 F.3d 1092, 1099 (10th Cir. 2019); 5 see

  Eaton v. Pacheco, 931 F.3d 1009, 1031 (10th Cir. 2019) (stating that the

  failure to address an issue in the reply brief constitutes a waiver of “any

  non-obvious responses” that the appellant could have made); United States

  v. A.S., 939 F.3d 1063, 1076 (10th Cir. 2019) (stating that we’re free to

  conclude that the appellant waived any non-obvious responses to the

  appellee’s argument by failing to address it in the reply brief).

        Though Dr. Seay and Dr. Jacobs waived any objections to non-

  obvious defects, we asked about the issue after Dr. Seay and Dr. Jacobs

  5
        In Hasan, we approvingly quoted a Seventh Circuit opinion: “When
  an appellee advances an alternative ground for upholding a ruling by the
  district judge, and the appellant does not respond in his reply brief . . . , he
  [does not] concede[] the correctness of the ruling . . . . But he waives, as a
  practical matter anyway, any objections not obvious to the court to specific
  points urged by the appellee.” 935 F.3d at 1099 (alterations in original)
  (quoting Hardy v. City Optical Inc., 39 F.3d 765, 771 (7th Cir. 1994)).

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  had completed their presentations in oral argument. 6 They responded to our

  questions on the issue. But their responses to our questioning don’t cure

  the waiver from their failure to address the issue in their reply brief. See

  Fed. Ins. Co. v. Tri-State Ins. Co., 157 F.3d 800, 805 (10th Cir. 1998)

  (appellate arguments are waived when presented for the first time in oral

  argument).

        After oral argument, we ordered supplemental briefing on mootness.

  The Plaintiffs responded, presenting their argument on mootness. But the

  Plaintiffs slipped into their supplemental brief a new response to the

  Board’s alternative argument for affirmance. Appellants’ Am. Supp. Br. on

  Mootness at 5. That was too late. We ordered briefing on mootness, not

  issues that could and should have been presented in the Plaintiffs’ reply

  brief. We thus confine our review to any obvious defect in the Board

  members’ alternative argument for affirmance.

        We haven’t squarely addressed how to consider obviousness in this

  setting. But the Supreme Court and our court have addressed obviousness

  when considering qualified immunity and plain error. In these settings, an

  error is ordinarily obvious only when it is apparent from precedent or the

  6
         At that time, we asked the Plaintiffs why they haven’t waived the
  Board members’ alternative argument for affirmance by failing to address
  it in the reply brief. Oral Arg. at 29:28–31:51. The Plaintiffs did not
  respond to this part of the question or otherwise suggest a reason for us to
  overlook the waiver. See id.
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  great weight of authority. See District of Columbia v. Wesby, 138 S. Ct.

  577, 589–90 (2018) (qualified immunity); United States v. Miller, 978 F.3d

  746, 763 (10th Cir. 2020) (plain error). This approach makes sense here.

  So we conclude that a defect in the Board members’ argument would

  ordinarily be obvious only in the presence of contrary precedent or the

  great weight of authority.

        3.    We see no obvious defect in the Board members’ alternative
              argument for affirmance.

        The Board members argued in their response brief that until the

  recent statutory amendment, they couldn’t issue specialty licenses in dental

  anesthesiology. We see no obvious defect in that argument.

        The Board is a creature of Oklahoma law, so the Board members

  drew their authority from the Oklahoma legislature. State ex rel. Okla.

  State Dep’t of Health v. Robertson, 152 P.3d 875, 880 (Okla. 2006). Until

  2021, Oklahoma law did not permit specialty licenses in dental

  anesthesiology. So the Board members could have reasonably considered

  themselves powerless to issue specialty licenses in dental anesthesiology.

        The Oklahoma Dental Act lists the specialties that could be

  recognized. Until 2021, that list omitted dental anesthesiology. Despite

  that omission, the Plaintiffs insisted at oral argument and in their

  supplemental brief on mootness that the Board members had the power to

  grant licenses for unlisted specialties.

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        Even if the Board had enjoyed this power, it wouldn’t be obvious to

  us. To determine the extent of the Board’s authority, we ordinarily start

  with the wording of the statute (the Oklahoma Dental Act). See

  Kingdomware Techs., Inc. v. United States, 579 U.S. 162, 171 (2016).

  When the Plaintiffs sued in 2017, the statute provided that “[t]he Board

  shall use the American Dental Association guidelines for the purpose of

  defining a specialty practice area.” Okla. Stat. tit. 59, § 328.22(D) (2015

  supp.) (emphasis added). 7 The use of the mandatory shall suggested that

  the Board could grant licenses only for the listed specialties. See Me.

  Cmty. Health Options v. United States, 140 S. Ct. 1308, 1320 (2020). Shall

  means “[h]as a duty to; more broadly, is required to.” Shall, Black's Law

  Dictionary (11th ed. 2019). “Unlike the word ‘may,’ which implies

  discretion, the word ‘shall’ usually connotes a requirement.”

  Kingdomware, 579 U.S. at 171.

        Oklahoma amended the statute in 2018, changing shall to may and

  allowing the Board to use either “the American Dental Association

  guidelines or the guidelines of another nationally recognized dental

  association or board for the purpose of defining a specialty practice area

  not otherwise defined [in the statute].” Okla. Stat. tit. 59, § 328.22(D)

  7
        The statute elsewhere identified dental specialties that the Board had
  to recognize. Okla. Stat. tit. 59 § 328.22(A)(3) (2015 supp.). These
  specialties did not include dental anesthesiology. See id.

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  (2018 supp.). 8 But at that time, the American Dental Association had not

  yet recognized dental anesthesiology as a specialty; 9 and the Plaintiffs have

  not identified another national organization that had recognized dental

  anesthesiology as a specialty.

        Dr. Seay and Dr. Jacobs point to accreditation of dental

  anesthesiology programs by the Commission on Dental Accreditation,

  arguing that accreditation allowed the Board to grant a specialty license in

  dental anesthesiology. But the Commission’s accreditation of a dental

  8
        In their opening brief, the Plaintiffs state that after the American
  Dental Association voted to approve dental anesthesiology as a specialty,
  the Oklahoma legislature amended the law in 2019 by changing shall to
  may. The Plaintiffs are mistaken. The statute was amended in 2018 (before
  the American Dental Association had recognized dental anesthesiology as a
  specialty). See Okla. H.B. 2759 (2017). The 2019 amendment dealt with
  another provision of the statute, Okla. Stat. tit. 59, § 328.22(A)(2) (2019
  supp.). See Okla. S.B. 603 (2019).

        In their supplemental brief on mootness, the Plaintiffs assert that the
  legislature amended the statute in 2019 “so that the Board could avoid
  granting licenses to anesthesiologists.” Appellants’ Am. Supp. Br. on
  Mootness at 5. But the Plaintiffs cite nothing for this assertion.
  9
        Anesthesia and Sedation, Amer. Dental Assoc.,
  https://www.ada.org/resources/research/science-and-research-institute/oral-
  health-topics/anesthesia-and-sedation (last updated Nov. 9, 2021) (noting
  that the American Dental Association recognized dental anesthesiology in
  March 2019); see Am. Acad. of Implant Dentistry v. Parker, 152 F. Supp.
  3d 641, 647 (W.D. Tex. 2016) (stating in 2016 that the American Dental
  Association did not recognize dental anesthesiology as a specialty), aff’d,
  860 F.3d 300 (5th Cir. 2017).

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  anesthesiology program does not show recognition as a specialty for

  licensing purposes. The Commission on Dental Accreditation notes:

        “Accreditation” is an evaluation process where an organization
        or agency (e.g., the Commission) uses experts in a particular
        field of interest or discipline (e.g., dental education) to define
        standards     of     acceptable     operation/performance      for
        universities/programs/organizations and measures compliance
        with them. Whereas “certification” is a process by which an
        organization (e.g., American Board of Oral and Maxillofacial
        Surgery) grants recognition of competence to an individual who
        has met predetermined qualifications specified by that entity.

  Comm’n on Dental Accreditation, FAQ About the Commission on Dental

  Accreditation (last visited May 3, 2022), available at

  https://coda.ada.org/en/accreditation/faq; see also Joint App’x vol. 4, at

  844 (“[The Commission on Dental Accreditation] has no role in specialty

  recognition.”). The Commission’s accreditation of a graduate dental

  program in dental anesthesiology does not constitute recognition of a

  specialty by a nationally recognized dental association.

        Dr. Seay and Dr. Jacobs point out that the Board “continue[d] to

  refuse to grant the licenses” after the 2018 amendment to the Oklahoma

  statute and the American Dental Association’s 2019 recognition of dental

  anesthesiology as a specialty. But Dr. Seay and Dr. Jacobs did not submit

  new complete applications following the American Dental Association’s

  recognition of dental anesthesiology. So the Board never had an

  opportunity to grant them licenses on this basis.

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          Given the statutory constraints on the Board’s authority and the

  Plaintiffs’ failure to submit new applications, we see no obvious defect in

  the Board members’ alternative argument for affirmance.

          But even if the Commission’s accreditation could somehow be

  considered recognition of a specialty in dental anesthesiology, the Board

  had no basis to act because

              Dr. Seay hadn’t reapplied after the 2018 amendment and

              Dr. Jacobs had withdrawn her application in 2019 and hadn’t
               reapplied until the legislature changed the law in 2021.

          4.   The Plaintiffs haven’t shown an obvious constitutional
               violation prior to the 2021 amendment.

          In oral argument, the Plaintiffs suggested that despite the Oklahoma

  Dental Act’s exclusion of dental anesthesiology as a recognized specialty,

  the Board members should nonetheless incur liability because they

  enforced the statute with knowledge that it was unconstitutional. Oral

  Argument at 29:35–31:54. A board member’s reliance on a state statute

  may prevent liability. See Lawrence v. Reed, 406 F.3d 1224, 1232 (10th

  Cir. 2005). But “some statutes are so obviously unconstitutional” that

  board members may incur liability for damages unless they “second-guess

  the legislature and refuse to enforce an unconstitutional statute.” Id. at

  1233.

          A constitutional violation would ordinarily have been obvious only if

  a precedent or the weight of authority had already deemed the state law
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  unconstitutional. See Part III(B)(2), above. But even now, the Plaintiffs

  point to no such case law.

        The Plaintiffs say that the prior statutory restrictions constituted

  denials of due process, equal protection, and free speech. But the Plaintiffs

  haven’t pointed to any meaningful support in the case law.

        In the context of discussing the statute of limitations, the Plaintiffs

  asserted that Dr. Seay had a property interest in a specialty license and was

  entitled to due process. This assertion consisted of this paragraph:

              The [district] court trivialized Plaintiff Seay’s right to due
        process of law. In April 2017, Seay filed an Application for a
        Specialty License. His application has never been considered by
        the Board. He has never been given an opportunity to be heard.
        The Board has defended the due process violation by pleading
        that Seay does not have a protected property interest in his
        license and is not entitled to due process. (JA III:444, Doc. 57;
        JA I: 26–27, Doc. 1.) This defense is contrary to law. Johnson v.
        Board of Governors of Registered Dentists, 1996 OK 41.

  Appellants’ Opening Br. at 17.

        But the only cited case, Johnson, wouldn’t have rendered a property

  interest obvious to the Board. There the court had addressed revocation of

  an existing license—not an applicant’s request for a new license. Johnson

  v. Bd. of Governors of Registered Dentists of State of Okla., 913 P.2d

  1339, 1345, corrected (Okla. 1996).

        The Plaintiffs also refer in their opening brief to a denial of equal

  protection. These references consist of three cursory assertions:

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        1.    Plaintiff filed an action pursuant to 42 U.S.C. § 1983
              claiming that under color of state law, they had been
              continuously deprived of their property and liberty interest
              without due process of law, denied equal protection,
              freedom of speech and restrained from competition in
              violation of 15 U.S.C. §§ 1–26 and the Oklahoma Antitrust
              Reform Act, 79 O.S. § 201, et seq.

              * * * *

        2.    [The Plaintiffs’] Complaint and Amended Complaint
              include violations of due process, equal protection and
              antitrust claims. These claims were ignored by the court.

              * * * *

        3.    This action was not just a lingering effect of a previous
              constitutional harm but a recent event in which Seay was
              treated differently than many of his peers. It also cost him
              clients. This is an equal protection allegation Plaintiffs are
              treated differently than other licensed dentists.

  Appellants’ Opening Br. at 1, 5, 18 (emphasis added).

       The Plaintiffs’ references to equal protection are just as cursory in

  their reply brief. There the Plaintiffs say, in addressing timeliness, that (1)

  the Board members have ignored the claim involving equal protection and

  (2) the denial of equal protection is ongoing. Appellants’ Reply Br. at 3–4.

       The Plaintiffs do not say in either their opening or reply brief how or

  why the Board’s failure to issue specialty licenses in violation of a state

  statute would have constituted a denial of equal protection. 10 We thus see

  10
        The Plaintiffs do assert that they were “treated differently than other
  licensed dentists.” Appellants’ Opening Br. at 18. But they do not explain
  this assertion or say how the different treatment would constitute a denial
  of equal protection.
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  no reason that the Board members would have recognized an obvious

  denial of equal protection in the prior statutory restrictions on specialty

  licenses.

        Finally, in discussing timeliness, the Plaintiffs make six cursory

  references to a right to free speech:

        1.    Plaintiffs filed an action pursuant to 42 U.S.C. § 1983
              claiming that under color of state law, they had been
              continuously deprived of their property and liberty
              interests without due process of law, denied equal
              protection, freedom of speech and restrained from
              competition in violation of 15 U.S.C. §§ 1–26 and the
              Oklahoma Antitrust Reform Act, 79 O.S. § 201, et seq.

              * * * *

        2.    The court held that Plaintiffs had known for years that their
              rights to speech had been violated . . .

              * * * *

        3.    What the decision means is that the court knows the statute
              violates Plaintiffs’ constitutional rights to speech right
              now and not just in the past, but is willing to let the
              unconstitutional statute stand and continue to injure
              Plaintiffs because they did not file suit within the two year
              statute of limitations.

              * * * *

        4.    [The Oklahoma Court of Appeals] held that the Board’s
              action violated [Dr. Jacobs’] First Amendment right to
              speech.

              * * * *

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        5.    The district court criticized the Plaintiffs because they
              knew that their right to speech had been violated for years
              and did nothing. This is not a fair or accurate statement.

              * * * *

        6.    The [district] court stated that, “Plaintiffs’ chief complaint
              is that their rights have been violated because the subject
              laws and regulations prohibit them from representing
              themselves to the public as specialists.” (JA V: 918, Doc.
              67.) This statement belittles the importance of Plaintiffs’
              right to speech, the development of their professional lives
              and the ability to compete in business.

  Appellants’ Opening Br. at 1, 4, 12, 20 (emphasis added). The Plaintiffs’

  reply brief contains no further explanation for the asserted denial of free

  speech. See Appellants’ Reply Br. at 2–3.

        Even when discussing timeliness, the Plaintiffs haven’t said how or

  why the prior statutory restrictions on specialty licenses had infringed on a

  right to free speech. So even if the prior statutory restrictions had

  infringed on a constitutional right to free speech, the infringement

  wouldn’t have been obvious to the Board members.

                                       * * *

        In the absence of any explanation or authority, we see no obvious

  defect in the Board members’ argument for affirmance on an alternative

  ground. If a constitutional infirmity in the Oklahoma Dental Act had been

  obvious, the Board couldn’t rely on the legislature’s constraints on

  specialty licenses. But the Plaintiffs haven’t pointed to any obvious

  constitutional infirmities in the statute.
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        So we need not address timeliness of the constitutional claims for

  damages. Even if these claims had been timely, we see no obvious defect in

  the Board members’ alternative argument for affirmance. Without an

  obvious defect in that argument, we affirm the award of summary judgment

  based on the Board members’ lack of statutory authority to issue the

  specialty licenses.

  IV. Judge Bacharach’s law clerk had no conflict of interest.

        In seeking rehearing, the Plaintiffs argue that a law clerk for Judge

  Bacharach developed a conflict of interest from working roughly 30 years

  ago on an administrative appeal in Oklahoma state court involving Dr.

  Jacobs. 11 This argument reflects a misunderstanding of the ethical rules for

  law clerks and the nature of the administrative appeal.

        Judicial law clerks are governed by the Code of Conduct for Judicial

  Employees. Gregory Bischoping, Reconceiving Ethics for Judicial Law

  Clerks, 12 St. Mary’s J. Legal Mal. & Ethics 58, 71 (2021). The Code’s

  Canon 3F addresses disqualification. See Mathis v. Huff & Puff Trucking,

  Inc., 787 F.3d 1297, 1309 (10th Cir. 2015) (“The Code of Conduct for

  Judicial Employees sets forth specific rules governing law clerk conflicts

  11
        “Of course, ‘[i]f a clerk has a possible conflict of interest, it is the
  clerk, not the judge, who must be disqualified.’” Mathis v. Huff & Puff
  Trucking, Inc., 787 F.3d 1297, 1311 (10th Cir. 2015) (quoting Hunt v. Am.
  Bank & Tr. Co., 783 F.2d 1011, 1016 (11th Cir. 1986)).

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  of interest.”). Under this canon, judicial law clerks are disqualified if they

  “served in governmental employment and in such capacity participated as

  counsel, advisor, or material witness concerning the proceeding, or ha[ve]

  expressed an opinion concerning the merits of the particular case in

  controversy.” Code of Conduct for Judicial Employees, Canon 3F(2)(a)(v)

  (emphasis added). 12

        The Plaintiffs seek rehearing, arguing that Judge Bacharach’s law

  clerk prosecuted Dr. Jacobs in this case in the early 1990s. This argument

  mischaracterizes the law clerk’s role as well as the nature of the

  administrative appeal.

        In the early 1990s, the Oklahoma Board of Dentistry reprimanded Dr.

  Jacobs for advertising as a specialist on the ground that her advertisements

  had been misleading. Dr. Jacobs appealed in state district court and won.

  The Oklahoma Board of Dentistry then appealed, and the Oklahoma Court

  of Appeals affirmed.

        At that time, a law clerk for Judge Bacharach represented the

  Oklahoma Board of Dentistry in state district court and in the Oklahoma

  Court of Appeals. In these proceedings, Dr. Jacobs never suggested that

  12
        Judicial law clerks are also disqualified if they harbor personal bias
  or have personal knowledge of disputed evidentiary facts concerning the
  proceedings. Code of Conduct for Judicial Employees, Canon 3F(2)(a)(i).
  But the Plaintiffs do not suggest that the law clerk had personal bias or
  personal knowledge of a disputed evidentiary fact.
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  she was eligible for a specialty license. To the contrary, she argued simply

  that her advertisements were truthful and protected by the First

  Amendment. As Dr. Jacobs says in her opening appeal brief in our case,

  “[t]he Jacobs case was limited to the violation of her right to speech.”

  Appellant’s Opening Br. at 4. She also explained in our oral argument that

  even though she had won in state court, she later sued in federal court so

  that she could expand her advertising to show that she has obtained a

  specialty license—something that hadn’t sought in her administrative

  appeal roughly 30 years ago: “[T]he [Oklahoma] Court of Appeals said . . .

  that discipline was inappropriate or wrong because it violated [Dr. Jacobs’]

  constitutional rights. It did not strike down the law. It did not declare it

  was unconstitutional. It didn’t do anything to the law and the law remained

  on the books. What Dr. Jacobs and Dr. Seay would like to do is advertise

  and represent themselves to the public and let the public know that they

  hold a specialty license in anesthesiology in the state of Oklahoma.” Oral

  Arg. at 9:54–10:23.

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        The administrative appeal of roughly 30 years ago is not the same

  proceeding as ours. 13 So the Code of Conduct for Judicial Employees did

  not require recusal of Judge Bacharach’s law clerk. 14

  V.    Conclusion

        The Plaintiffs’ claims for prospective relief against the Board are

  prudentially moot in light of the recent amendment to the Oklahoma Dental

  Act and the Board’s softening of its position.

        We affirm the award of summary judgment on the claims for damages

  against the Board members. On these claims, the Plaintiffs waived an

  appellate challenge on their theory under the antitrust laws. On the

  Plaintiffs’ constitutional theories, the Board members couldn’t incur

  personal liability because they couldn’t grant the specialty licenses to Dr.

  Seay and Dr. Jacobs.

        Affirmed.

                                      Entered for the Court

                                      Robert E. Bacharach
                                      Circuit Judge

  13
        The issues also differ: Our appeal doesn’t address the truthfulness of
  Dr. Jacobs’ advertising, and the administrative appeal didn’t involve her
  eligibility for a specialty license.
  14
        The law clerk did no substantive work in this case.
                                        29