17 Ways To Lose A Winning Argument In Court, and the Implications for Mediation

First Published  by Law360 and later revised:

Expert Analysis

Photo of Richard Seymour
Richard T. Seymour

Nothing stings worse than losing a winning claim or defense because of a mistake.

In the course of reading several thousand published appellate decisions in federal courts for 15 volumes of “Equal Employment Law Update,” published by the Bureau of National Affairs (now Bloomberg BNA) for the American Bar Association Section of Labor and Employment Law from 1996 to 2007, and in the course of reading many hundreds more decisions for the annual updates on employment law I’ve done for the Arizona and Pennsylvania state bars, the National Employment Lawyers Association, and the American Law Institute CLE, I have been struck by the number of ways to lose a case besides, well, having a losing claim or defense.

Waivers happen, and they happen to all sizes of law firms, and to plaintiffs and defendants alike. I am not speaking of the waivers associated with releases, which are generally protected by the “knowing and voluntary” standard, or the waiver on a ticket stub that may or may not be enforceable, but the unknowing and unintended waivers that arise in litigation, the kind that bar a winning argument or defense because it was raised too late. The following recent labor and employment law examples show that waivers by both sides do happen, when an argument:

  • was not raised in objection to a magistrate judge’s recommendation for the grant of summary judgment;[1]
  • consisted of an arbitration agreement, where the defendant did not plead the agreement as an affirmative defense and waited too long, and litigated too much, to assert the agreement belatedly;[2]
  • was stipulated to be inapplicable;[3]
  • was raised for the first time in objections to a magistrate judge’s recommendation for the grant of summary judgment, meaning that the magistrate judge has been sandbagged;[4]
  • was raised below for the first time in oral argument;[5]
  • was raised below for the first time in a motion to reconsider summary judgment;[6]
  • was raised for the first time on appeal, meaning that the lower court has been sandbagged;[7]
  • involved an erroneous jury instruction that was not objected to below and can now be reviewed only for plain or clear error, to prevent manifest injustice;[8]
  • was appealed by the wrong person, such as when a sanction running only against an attorney is appealed only by a party and not by counsel;[9]
  • was raised on appeal, but only by incorporating a submission to the district court;[10]
  • was raised at the proper time, but was not adequately developed in the appellate brief;[11]
  • was not briefed at all;[12]
  • was not addressed in the appellant’s reply brief on appeal, where the appellee raised the issue in its brief;[13]
  • was raised for the first time in a reply brief on appeal, meaning that the opponent has not been given a fair opportunity to respond to it before the argument;[14]
  • was raised for the first time in oral argument on appeal;[15]
  • was raised for the first time in a Federal Rules of Appellate Procedure Rule 28(j) letter after briefing was completed;[16] or
  • was raised for the first time in a petition for rehearing of the panel decision.[17]

Surviving a Waiver

Not all these situations are fatal. Opposing counsel who know what they are doing will sometimes persuade their clients to agree to waive the waiver. I’ve done it myself.

One situation in which this happens is when the law has recently changed, or such compelling new facts have emerged, that it strikes even opposing parties and counsel that it would be unfair not to excuse the waiver. Attorneys should not have to have a court tell them it would be unfair, unless they need to do so to protect themselves from an untrustworthy client who will then use this as an excuse to sue their own counsel if the case goes badly.

Another situation in which this happens is when the law on the question at issue is sufficiently unclear that a case can be diverted onto side rails for years because of the waiver question, and can even result in an otherwise unnecessary appeal.

Contrary to the usual assumptions of plaintiffs lawyers, defendants do not always embrace delay as a means of wearing out plaintiffs and driving down their demands. Corporate and agency officials often want to bring cases to a quick end, to avoid the distraction of senior officials and to control the risks their organizations face. Plaintiffs counsel can test my perception by asking defense lawyers of their acquaintance what percentage of them would like to see cases last for years and be taken all the way up to the U.S. Supreme Court. I suspect the response will usually be a wince.

A third situation in which this happens is when the waiver is not dispositive of the opponent’s entire case or defense, and the bulk of the case will survive despite a waiver. Highly skilled counsel do not contest every conceivable point, and the game may not be worth the candle to the opponent.

Excusing an opponent’s waiver can sometimes be a smart strategy. Cases are more quickly and satisfactorily resolved when there is good will among the opposing parties and their counsel, and a sense of trust in being treated fairly. Excusing a waiver is a confidence-building measure that can smooth the path to an agreement that lets everyone get on with their lives.

Counsel faced with an opponent’s waiver should also consider that opposing counsel may be in a difficult situation with her or his client because of counsel’s mistake. Clients are not always benefited when there is infighting on the other side. Infighting on one side can stall everything, and trigger acrimony that makes litigating and resolving the case more difficult. Removing the other side’s internal irritant may help our clients even more than the other side.

These are all exceptions, of course. In the usual situation, both plaintiffs and defendants are best served by enforcing the other side’s waiver. If the other side has engaged in deceit or oppressive tactics, I suspect that both plaintiffs and defendants are always best served by enforcing the deceitful or oppressive side’s waiver.

Sometimes, of course, a court will excuse a waiver.  As the cases in the endnotes demonstrate, however, courts are closely attuned to prejudice suffered by the opposing party and often will not excuse a party’s waiver.

If the opposing party has in its conduct or litigation positions managed to irritate the court sufficiently, the court may simply blow past the question of waiver and even allow a post-verdict amendment of a complaint to encompass relief awarded by the jury that could not have been entered in a judgment under the original complaint.[18]

How This Plays Out in Mediation

This topic has teeth even in advance of a judicial determination of waiver, and even in advance of either party’s awareness of its waiver.

When I am acting as a mediator, I cannot ethically tell the plaintiff that she or he is overlooking a powerful additional claim or way of shaping the existing claim, and cannot ethically tell the plaintiff that she or he is overlooking a major hole in the employer’s defense.

Similarly, I cannot ethically tell the defendant that it is overlooking a powerful defense or a major flaw in the plaintiff’s case.

What I can do for each side is to point out the particular risks of continued litigation. My most persuasive tool with a recalcitrant party, where the opportunity exists, is to point out that the other side has not yet realized something that might greatly strengthen its position, or require it to dig expensively deeper and fight expensively harder, but that the other side still has time to realize the problem and correct it if the case does not settle.

The better the other side’s counsel, the more persuasive I can be that the penny will eventually drop, making any resolution much more expensive either in increased settlement value or increased transaction costs.

For now, the takeaway is that it is important for attorneys on both sides of a case to do some serious thinking about the issues in the beginning of the case, and not wait until it is too late. Few things are more dangerous than concluding, too early, that a claim or defense is a surefire “slam dunk.” Excessive confidence is seldom good for one’s client.

Richard T. Seymour is an arbitrator and mediator, and negotiator and litigator at the Law Office of Richard T. Seymour PLLC in Washington, D.C.

The opinions expressed are those of the author(s) and do not necessarily reflect the views of the firm, its clients, or Portfolio Media Inc., or any of its or their respective affiliates. This article is for general information purposes and is not intended to be and should not be taken as legal advice.

[1] E.g., EEOC v. Memphis Health Center Inc., 526 Fed.Appx. 607, 611 n. 1 (6th Cir. 2013) (ADEA and Equal Access to Justice Act claim by employer for attorneys’ fees award against EEOC) (employer’s waiver) (“MHC has waived any argument that the age discrimination claim was not substantially justified because it failed to object to the magistrate judge’s findings on this point.”); Self v. I Have A Dream Foundation-Colorado, 552 Fed.Appx. 782, 787 (10th Cir. 2013) (ADA) (“‘We have adopted a firm waiver rule when a party fails to object to the findings and recommendations of the magistrate [judge]. The failure to timely object to a magistrate [judge]’s recommendations waives appellate review of both factual and legal questions.’ Duffield v. Jackson, 545 F.3d 1234, 1237 (10th Cir.2008) (citation, brackets, and internal quotation marks omitted). Exceptions exist when: (1) the district court does not notify a pro se litigant of the time period for objection and the consequences of a failure to object, and (2) review is required in the interests of justice. Id.”).

[2] E.g., Chassen v. Fid. Nat’l Fin. Inc., 836 F.3d 291, 295 (3d Cir. 2016) (“Given this strong preference to enforce arbitration agreements, we have concluded that a party waives the right to arbitrate “only where the demand for arbitration came long after the suit commenced and when both parties had engaged in extensive discovery.” PaineWebber Inc. v. Faragalli, 61 F.3d 1063, 1068–69 (3d Cir. 1995) (internal quotation marks and citation omitted).”), but holding that there is no waiver where an earlier invocation of arbitration would have been futile. Peterson v. Shearson/Am. Exp. Inc., 849 F.2d 464, 467–68 (10th Cir. 1988), set out a six-factor test:

… In determining whether a party has waived its right to arbitration, this court examines several factors: (1) whether the party’s actions are inconsistent with the right to arbitrate; (2) whether “the litigation machinery has been substantially invoked” and the parties “were well into preparation of a lawsuit” before the party notified the opposing party of an intent to arbitrate; (3) whether a party either requested arbitration enforcement close to the trial date or delayed for a long period before seeking a stay; (4) whether a *468 defendant seeking arbitration filed a counterclaim without asking for a stay of the proceedings; (5) “whether important intervening steps [e.g., taking advantage of judicial discovery procedures not available in arbitration] had taken place”; and (6) whether the delay “affected, misled, or prejudiced” the opposing party. Reid Burton Constr., Inc. v. Carpenters Dist. Council of S. Colorado, 614 F.2d 698, 702 (10th Cir.), cert. denied, 449 U.S. 824, 101 S.Ct. 85, 66 L.Ed.2d 27 (1980).

The Sixth Circuit has articulated a two-factor test. It stated in Johnson Assocs. Corp. v. HL Operating Corp., 680 F.3d 713, 717 (6th Cir. 2012):

We have explained that “a party may waive an agreement to arbitrate by engaging in two courses of conduct: (1) taking actions that are completely inconsistent with any reliance on an arbitration agreement; and (2) ‘delaying its assertion to such an extent that the opposing party incurs actual prejudice.’” Hurley, 610 F.3d at 338 (quoting O.J. Distrib. Inc. v. Hornell Brewing Co., 340 F.3d 345, 356 (6th Cir.2003)); see Gen. Star Nat’l Ins. Co. v. Administratia Asigurarilor de Stat, 289 F.3d 434, 438 (6th Cir.2002).

The court also held that failure to assert the defense of an arbitration agreement in an answer is strong evidence of an intent to litigate the dispute rather than arbitrate it:

Regardless of whether a defendant is required to raise arbitration as a defense under Rule 8(c), a defendant’s failure to raise arbitration as an affirmative defense shows his intent to litigate rather than arbitrate. The filing of an answer is, after all, the main opportunity for a defendant to give notice of potentially dispositive issues to the plaintiff; and the intent to invoke an arbitration provision is just such an issue. Indeed, as a practical matter, an enforceable contractual right to compel arbitration operates as a quasi-jurisdictional bar to a plaintiff’s claims, providing grounds for dismissal of the suit. It is therefore unsurprising that defendants routinely raise the right to arbitration in their answer, whether it is technically required by Rule 8 or not. …

Id. at 718.

[3] E.g., Holder v. Illinois Dept. of Corrections, 751 F.3d 486, 493 (7th Cir. 2014) (FMLA) (defendant’s waiver) (“Once the State and Holder entered into a stipulation about the sixtieth day, that issue had been removed from the jury. The State could have appealed the summary judgment holding on this matter (more on this below), but instead made the tactical decision to argue that its agreement to pay rendered the issue moot. When a party selects among arguments as a matter of strategy, he also waives those arguments he decided not to present.”);  Connelly v. Metropolitan Atlanta Rapid Transit Authority, 764 F.3d 1358, 1365 (11th Cir. 2014) (Title VII and § 1981; plaintiff’s argument that defendant waived attorney-client privilege was itself waived) (“Connelly stipulated before trial that O’Neill would testify about a narrow set of issues and that Connelly would not seek to elicit any privileged communications from O’Neill at trial.”).

[4] E.g., Garayalde-Rijos v. Municipality of Carolina, 747 F.3d 15, 22 (1st Cir. 2014) (Title VII and Puerto Rican law) (“Similarly, Garayalde–Rijos’s failure to object specifically to the magistrate judge’s recommendation that her post-hire Title VII discrimination claim against Carolina be dismissed for lack of exhaustion of administrative remedies waives her right to this court’s review of that claim.”); Self v. I Have A Dream Foundation-Colorado, 552 Fed.Appx. 782, 784-85 (10th Cir. 2013) (ADA) (“The Plaintiff bases her first argument largely on the cover page to the Foundation’s ‘Form 990,’ which purported to list 26 employees of the Foundation. But Ms. Self did not submit this page in response to the summary judgment motion; instead, she submitted it in her objection to the magistrate judge’s report. R. at 1136. As a result, the district judge declined to consider the form. That ruling was permissible. See Fed.R.Civ.P. 72(b)(3).”).

[5] E.g., In re Community Bank of Northern Virginia, 622 F.3d 275, 288 n. 12 (3d Cir. 2010) (home equity lending case) (“Because the Objectors did not challenge the appointment until oral argument before Judge Ziegler — and despite having six weeks between receiving notice of the appointment and the argument — they have waived this challenge, and we decline to address it. See, e.g., Fajardo Shopping Ctr., S.E. v. Sun Alliance Ins. Co. of P.R., 167 F.3d 1, 6 (1st Cir.1999).”).

[6] E.g., Rivera-Diaz v. Humana Insurance of Puerto Rico Inc., 748 F.3d 387, 390 (1st Cir. 2014) (ADA and Puerto Rican law) (“While it is true that matters that are raised for the first time in a motion for reconsideration are usually deemed waived … everything depends on context.”); Smith v. Aegon Companies Pension Plan, 769 F.3d 922, 933 (6th Cir. 2014) (ERISA benefits) (“But Smith did not raise this argument until his … Rule … 59 motion to alter, vacate, or amend the district court’s judgment, and he has waived it.”) (footnote omitted).

[7] E.g., Ray v. United Parcel Service, 587 Fed.Appx. 182, (5th Cir. 2014) (FMLA) (defendant’s waiver) at p. *5 (“Turning to the third element, UPS challenges Ray’s prima facie showing of causation for the first time on appeal. Since UPS did not assert any argument against prima facie causation before the district court, UPS has waived this challenge on appeal. UPS acknowledges that the lower court did not specifically discuss causation in its analysis, but attempts to justify our consideration of its causation challenge by relying on the principle that we may affirm summary judgment ‘for any reason supported by the record.’ Equally well-settled, however, is the principle that the scope of appellate review on a summary judgment order is limited to matters that the parties presented to the district court, such that the district court has an opportunity to rule on the challenge. Though the district court necessarily and generally addressed Ray’s causation showing as part of the later stages of the mixed-motive analysis, a point advanced by UPS, the district court made no such ruling at the prima facie stage because UPS did not make prima facie causation an issue, an omission which was expressly noted by the district court. Of UPS’s arguments on appeal, only UPS’s arguments against comparators were presented to the district court, but then only as rebuttal to Ray’s pretext showing. Based on the principle that a party “must press and not merely intimate the argument during the proceedings before the district court,” we will not re-cast these elsewhere-asserted, comparator references as arguments against prima facie causation. Accordingly, UPS has waived any argument on appeal that Ray cannot establish prima facie causation.”) (emphasis supplied; footnotes omitted); Tank v. T-Mobile USA Inc., 758 F.3d 800, 803 (7th Cir. 2014) (§ 1981) (“this argument is waived because it was not raised below.”); Nichols v. Michigan City Plant Planning Dept., 755 F.3d 594, 600 (7th Cir. 2014) (Title VII) (“The non-moving party waives any arguments that were not raised in its response to the moving party’s motion for summary judgment.”) (dictum); Dalpiaz v. Carbon County, 760 F.3d 1126, 1131-32 (10th Cir. 2014) (FMLA) (Plaintiff waived FMLA retaliation claim by raising only an FMLA interference claim below); Ridgell-Boltz v. Colvin, 565 Fed.Appx. 680, 683 n.3 (10th Cir. 2014) (ADEA and Title VII) (“This argument is waived, however, because it was not advanced in the district court, nor does it appear in Plaintiff’s opening brief.”).

[8] E.g., Kroshnyi v. U.S. Pack Courier Services Inc., 771 F.3d 93, 106 n.23 (2d Cir. 2014) (FLSA, FUTA, New York Labor Law, etc.) (“Because plaintiffs failed to object to the jury instructions in the court below, however, they have waived this argument on appeal … and we perceive no manifest injustice that would warrant reaching this waived argument here.”).

[9] E.g., Kleehammer v. Monroe County, 583 Fed.Appx. 18, 20 (2d Cir. 2014) (Title VII) (“Kleehammer’s timely filed notice of appeal also expressed an intent to appeal from the Rule 11 sanction imposed on counsel. Because the district court did not sanction Kleehammer, there is no case or controversy with respect to her. ‘Where an award of sanctions runs only against the attorney, the attorney is the party in interest and must appeal in his or her name.’”).

[10] E.g., Weatherly v. Alabama State University, 728 F.3d 1263, 1273 (11th Cir. 2013) (Title VII; defendant’s waiver) (“ASU does not, however, make any arguments on this point, but rather, incorporates by reference the arguments it made before the district court. … Incorporating by reference to earlier filings is not a permissible way to present arguments to this court. … (“By attempting to ‘incorporate’ all of the arguments it made below, and thus exhorting this panel to conduct a complete review of its district court brief, [the party] … makes a mockery of our rules governing page limitations and length[.]”). ASU has therefore waived this argument as well.”) (citation omitted).

[11] E.g., Lydon v. Local 103, Int’l Bhd. of Elec. Workers, 770 F.3d 48, 53 (1st Cir. 2014) (LMRA, LMRDA) (“ The problem for Lydon is that his initial brief never specifically identifies the “numerous” papers that the judge should have pondered but did not. And it never explains how these unnamed documents fit … let alone explain how they could have pushed his complaint across the plausibility threshold. Given these circumstances, we hold the argument waived.”); Medina-Velazquez v. Hernandez-Gregorat, 767 F.3d 103, 109 n.6 (1st Cir. 2014) (First Amendment political discrimination) (defendants’ waiver) (“Appellees have not developed, and thereby waive, any argument regarding the first element”); Willis v. Cleco Corp., 749 F.3d 314, 319 (5th Cir. 2014) (Title VII and § 1981) (“This claim is waived because it is inadequately briefed.”); Boegh v. EnergySolutions, Inc., 772 F.3d 1056, 1063 (6th Cir. 2014) (whistleblower under Energy Reorganization Act and False Claims Act) (“Second, regarding the FLSA, Vander Boegh fails to fully develop this argument and therefore has abandoned it.”); Matthews v. Waukesha County, 759 F.3d 821, 826 (7th Cir. 2014) (Title VII and § 1981) (“It is not the province of the appellate court to search the record in order to discover the factual underpinnings of an argument, and we will not consider arguments that are not supported by relevant law. … This argument is waived.”).

[12] E.g., Kleehammer v. Monroe County, 583 Fed.Appx. 18, 20 (2d Cir. 2014) (Title VII) (“On appeal, she also waived any argument that defendants punished her rather than her coworkers, as she did not address this issue in her appellate brief.”); Reveles v. Napolitano, __ Fed.Appx. __, 2014 WL 7004789 (5th Cir. Dec. 12, 2014) (No. 13-51203) (Title VII) (“Because Reveles did not brief the defenses of equitable tolling and estoppel, such arguments have been waived.FN19” and “FN19. ‘Although we liberally construe the briefs of pro se appellants, we also require that arguments must be briefed to be preserved.’”).

[13] E.g., Velazquez-Perez v. Developers Diversified Realty Corp., 753 F.3d 265, 278-79 (1st Cir. 2014) (Title VII) (“Velázquez files no reply brief responding to this argument. Nor does Velázquez’s opening brief develop or even suggest any counter-argument. Our task is not to go through a record and see if a losing party may have developed an argument that it did not raise on appeal.”).

[14] E.g., Emory v. United Air Lines Inc., 720 F.3d 915, (D.C.Cir. 2013), cert. denied, 134 S.Ct. 1520 (2014) and sub nom. Adams v. United States, 134 S.Ct. 1540 (2014) (Fair Treatment for Experienced Pilots Act, Due Process Clause, and DFR) (“We accordingly find that the Emory plaintiffs waived their BFOQ arguments on appeal, having raised them for the first time in their reply brief.”); KLB Industries Inc. v. NLRB, 700 F.3d 551, 558-59 (D.C.Cir. 2012) (NLRA) (“To the extent KLB now contends the dividing line between Nielsen’s “open your books” disclosure obligation and the instant information request is arbitrary and capricious, that argument is waived because it first appeared in the company’s reply brief.”); Rives v. Whiteside School Dist. No. 115, 575 Fed.Appx. 678, 680 (7th Cir. 2014) (Title VII and § 1981) (“In her reply brief Rives challenges for the first time the dismissal of her claims of sexual harassment and retaliation, but she waived these arguments by not mentioning them in her opening brief.”); Johnson v. Orkin LLC, 556 Fed.Appx. 543, 545 (7th Cir. 2014) (Tile VII and Illinois law) (“In any case, Johnson waived this argument on appeal by raising it for the first time in his reply brief, giving Orkin no chance to respond.”); Ridgell-Boltz v. Colvin, 565 Fed.Appx. 680, 683 n.3 (10th Cir. 2014) (ADEA and Title VII) (“This argument is waived, however, because it was not advanced in the district court, nor does it appear in Plaintiff’s opening brief.”).

[15] E.g., Maloy v. Ballori-Lage, 744 F.3d 250, 254 (1st Cir. 2014) (First Amendment) (“We also reject Maloy’s claim, presented at oral argument, that Díaz Ogando retaliated against her by telling her that the application required materials that Maloy argues were not in fact required. Maloy did not so argue in opposing the motion to dismiss or in her brief on appeal. See, e.g., Ortiz v. Gaston Cnty. Dyeing Mach. Co., 277 F.3d 594, 598 (1st Cir. 2002) (“[F]ailure to brief an argument will result in waiver for purposes of appeal.”).”); Holland v. Gee, 677 F.3d 1047, 1065-66 (11th Cir. 2012) (Title VII and Florida Civil Rights Act) (court will not consider issue first raised at oral argument).

[16] Ross v. Gilhuly, 755 F.3d 185, 192 n. 11 (3d Cir. 2014) (FMLA) (“In an April 17, 2014, letter filed pursuant to Rule 28j of the Federal Rules of Appellate Procedure, Ross recasts his interference claim to assert that he had somehow been discouraged from taking FMLA leave. In addition to Ross having waived that argument by failing to advance it in briefing …”).

[17] E.g., Shields v. Illinois Dept. of Corrections, 746 F.3d 782, 800-01 (7th Cir. 2014), petition for cert. filed, 83 USLW 3306 (Oct. 13, 2014) (Nos. 14-476, 14A23) (§ 1983 claim for denial of medical care) (Tinder, J., concurring: “Our sister circuits that have spoken on this question agree with our determination on this matter: in general, new issues raised in petitions for rehearing are not eligible for review. Numerous circuits hold that an issue raised for the first time in a petition for rehearing has been waived and cannot be reviewed. Some hold that this practice constitutes forfeiture rather than waiver. At least two circuits opt for a flexible waiver principle, where the court occasionally chooses to consider arguments raised for the first time in a petition for rehearing, in extraordinary cases. But no case—in our circuit or elsewhere—allows for a party to freely raise a new theory of its case in a petition for rehearing, one that it has repeatedly declined to raise in the district court or in its briefs before us.”) (footnotes omitted).

[18] See Baker v. John Morrell & Co., 382 F.3d 816, 830–32 (8th Cir. 2004), allowing post-verdict amendment of claims to add claims under the Iowa Civil Rights Act to the Title VII claims on which the case was pleaded and tried, because the defendant was on notice that the plaintiff sought an amount in excess of that allowed under the caps on damages for Title VII claims.  The court cited evidence of extreme harassment and employer indifference, leading eventually to the plaintiff’s constructive discharge.  The court stated:

By April 4, 2001, Baker’s treating psychiatrist had diagnosed her with major depressive disorder, single episode, and post-traumatic stress disorder and panic disorder. Baker was hospitalized on April 4, 2001, because of an overdose. Baker’s brother testified he went to her house and found her “lifeless” in bed. Baker was transferred to a psychiatric unit where her psychiatrist classified the event as a suicide attempt and restricted Baker from going back to work because the presenting factor in her condition was her work environment.

Id. at 826.