Although reply briefs are optional, it is generally advisable to file a reply brief lest the respondent's unanswered arguments take hold before oral argument is heard or the lack of a reply is viewed as a concession of the validity of those arguments. More to the point, few lawyers can resist the temptation of having the last word when the opportunity presents itself.

A reply brief's mission is different from an opening brief. A reply gives the appellant an opportunity to answer the questions the reviewing court may have after reading the respondent's brief. The court may need to know more about the key facts, the relevant case or statutory law, or the policy considerations that militate against the respondent's position. All too often, however, reply briefs fall into one of two categories: one that merely rehashes the appellant's main arguments without replying to the respondent's opposing arguments in any meaningful fashion, or one that goes tit-for-tat with every factual and legal argument in the respondent's brief. These types of reply briefs do little to advance the appellant's cause and should be avoided.

Rules of Practice

First, a few words about the formal requirements for reply briefs. Rule 1250.8(b) of the statewide Practice Rules of the Appellate Division (22 NYCRR Part 1250) prescribes the form and contents of an appellant's opening brief. Rule 1250.8(d) provides that "[a]ny reply brief of the appellant or cross appellant shall conform to the requirements of subdivision (b), without repetition." Theoretically, this would include a statement of the questions involved with the answer of the court below, a statement of the nature of the case and relevant facts, and the argument divided into points by distinctive headings (see 22 NYCRR 1250.8[b]). In practice, there is far greater flexibility in preparing the reply brief than the appellant's brief. Indeed, the customary format consists of reply points only, without redundant preliminary statements, questions presented or the like.

On cross-appeals, the appellant-respondent's reply brief must include the points of argument in response to the cross-appeal (see Rules 1250.8[d] and 1250.9[f][1][v]). The respondent-cross appellant may file a reply brief limited to the issues raised on the cross-appeal after receipt of the appellant's reply brief (see Rule 1250.9[f][1][vi]). In normal course appeals, the Court of Appeals has similar rules for the content and filing sequence of reply briefs (see 22 NYCRR 500.12[d]). Neither the Appellate Division nor the Court of Appeals permits sur-reply briefs (see Rule 1250.8[e] and Rule 500.12[g]).

Reply briefs should be as concise as possible. For counsel who struggle with the concept that brevity is the soul of wit, the Appellate Division and Court of Appeals have a 7,000-word limit for reply briefs (see Rule 1250.8[f][2] and Rule 500.13[c][1])).

Structuring the Reply Brief

Preliminarily, an appellant's opening brief should set the stage for the reply brief. In addition to presenting the appellant's factual and legal arguments, an effective opening brief preemptively addresses the less favorable aspects of the appellant's case, i.e., the most damaging facts and case law, before the respondent's brief does. This serves two purposes: It lessens the potential impact of the respondent's brief by undercutting any argument that the appellant's opening brief omitted "crucial" facts or ignored "dispositive" case law, and it allows the reply brief to principally focus on the respondent's concessions and weak points, while reinforcing the appellant's strongest points.

After thoroughly analyzing the respondent's brief, the appellant's counsel should ask two basic questions: What questions will the court have after reading the respondent's brief, and what are the greatest factual and legal vulnerabilities of both side's positions? The answer to these questions will determine the content of the reply brief and serve as a starting point for oral argument preparation. It is often useful to have a "stranger" to the appeal—for example, a work colleague with no prior exposure to the case—read the appellant's and respondent's briefs for a fresh perspective on these important questions.

After determining what you want to say in your reply brief, the next issue is the order in which you want to say it. If the respondent's counsel is a skillful appellate advocate, he or she will have organized the respondent's brief by presenting his or her strongest arguments first, regardless of the order of the points in the opening appellant's brief. For this reason, it is usually a mistake to adopt the organization of the respondent's brief by replying to each of the respondent's arguments in the order in which they appear. Rather, a reply brief generally should follow the same organizational structure of the opening appellant's brief as a means of refocusing the court on the principal issues.

Once the content and order of the reply points has been established, several basic considerations should be kept in mind in writing the reply brief. The following list is illustrative, not exhaustive.

First, a reply brief should not attempt to correct every point of disagreement or minor factual inaccuracy in the respondent's brief. Rather, it should address and correct material factual misstatements made by the respondent that are potentially outcome-determinative. There are creative ways of doing so. For example, if the respondent's brief misstates one or more critical facts, a chart or table in the following format can be used to challenge such misstatements in a way that is visually attractive, easy to understand and effective in arguing the case on the basis of the record facts.

Second, a reply brief should not address every legal argument made by the respondent, no matter how peripheral. Rather, it should concentrate on the key legal issues in the case, not only rebutting the respondent's principal arguments, but also re-emphasizing the appellant's principal arguments. Again, the goals are to identify and answer the questions that the court will most likely have after reading the respondent's brief, to reply to arguments that ostensibly undercut the appellant's position, and to restore the court's focus to the appellant's main arguments in a concise and non-repetitive manner.

Third, a reply brief should not distinguish every case cited by the respondent (all of which should immediately be cite and substance checked upon receipt of the respondent's brief). Generally, only the respondent's "lead" authorities warrant detailed analysis. If the respondent's brief string cites multiple cases standing for the same general proposition, then the reply brief should address them on a global rather than individual basis. In some instances, this can be done in a footnote. A reply brief is a useful vehicle for bringing to the court's attention a controlling or persuasive case decided after the filing of the appellant's main brief. This underscores the importance of continuing to research the law up to the date of filing of the reply brief, and then, right up to the date of oral argument.

Finally, in the case of a cross-appeal, the appellant-respondent's reply brief must include the points of argument in response to the cross-appeal, i.e., a reply on the main appeal and answer to the cross-appeal in one document. It is generally advisable to address the cross-appeal in the last section of any such combined brief because a disposition in the appellant's favor on the main appeal may well render the cross-appeal academic. In drafting an answer to the cross-appeal, the appellant-respondent should adopt a respondent's mindset for purposes of the cross-appeal. For example, as a preliminary matter, the court's jurisdiction to entertain the cross-appeal should be considered: is the cross-appellant truly "aggrieved" by the order or judgment from which the cross-appeal has been taken, or is the cross-appeal a pretext for the cross-appellant to gain the last word through a reply brief on the cross-appeal? If the latter, a motion to dismiss the cross-appeal is in order.

Scope of a Reply Brief

While it may seem obvious, it is worth stressing that the proper purpose of a reply brief is to reply, not to present new arguments or matters at a time when the other party can no longer respond to them. As the court stated in the oft-cited State Farm Fire and Casualty Co. v. LiMauro decision, 103 A.D.2d 514 (2d Dept. 1984), aff'd, 65 N.Y.2d 369 (1985), "[i]t is beyond cavil that raising a new substantive issue of law for the first time in a reply brief is improper." This is one of the principal grounds for motion practice concerning the proper scope of reply briefs. Even arguments of a constitutional dimension may be deemed waived when improperly raised for the first time in a reply brief. See, e.g., Schulz v. New York State Executive, 233 A.D.2d 43 (3d Dept. 1997).

There is no hard and fast rule as to what constitutes a truly "new" substantive argument in a reply brief. For example, the respondent in State Farm moved to strike the references to Florida law in the appellant's reply brief on the ground the appellant's main brief had relied on New York law and did not raise any choice of law issue. The court denied the motion to strike on the ground that the appellant's reply brief "merely cites Florida law as persuasive, not controlling, authority." See 103 A.D.2d at 521.

A motion to strike is the proper remedy for an improper reply brief. In some instances, the court may strike only the offending portion of an otherwise acceptable reply brief, see, e.g., Brosnan v. Behette, 243 A.D.2d 524 (2d Dept. 1997), or the court may simply disregard the new arguments or matters raised for the first time in a reply brief, even without a motion to strike, see, e.g., Turner v. Canale, 15 A.D.3d 960 (4th Dept. 2005).

As it is, appellants usually face an uphill battle. This underscores the importance of making the last word in a reply brief count.

Thomas R. Newman is of counsel to Duane Morris and author of "New York Appellate Practice" (Matthew Bender). Steven J. Ahmuty Jr. is retired from Shaub, Ahmuty, Citrin & Spratt. They are members of the American Academy of Appellate Lawyers.