I have been contemplating this column for quite some time.  Years, in fact.

Pleadings are both an art and a science.  That is true whether we focus on complaints, answers, cross-claims, affirmative defenses, counterclaims, replies to counterclaims, third party complaints and answers, or intervenors.  Wow, everyone gets to jump in.  The primary purpose of a pleading is notice (N.Y. Civ. Proc. Law & Rules [“CPLR”} § 3013; Rapoport v. Schneider, 29 N.Y.2d 396, 403 [1972]). 

The priorities of an attorney differ depending on how the client is postured in a litigation.  Let us start with complaints.  In drafting a complaint, counsel must consider all of the conceivable non-frivolous causes of action applicable to the facts.  Once conceived, each cause of action must be spelled out in the complaint.  In drawing the specific causes of action, counsel must provide notice of the transactions or occurrences intended to be proven and address the elements of each separate cause of action (CPLR § 3013).  For instance, if a claim is for defamation, the complaint should allege each of the relevant elements --- the specific statement, its untruth, its defamatory character or defamation per se when applicable, its publication to a third party, the intent to defame, the knowledge of the defamer that the statement was false, and damages (unless the action involves defamation per se in which damages need not be pleaded and proved) (e.g., Arsenault v. Forquar, 197 A.D.2d 554 [N.Y. App. Div., 2d Dep’t 1993]).  If the complaint fails to allege a necessary element expressly or by at least by inference (Johnson ex rel. Fredo v. Verona Oil, Inc., 36 A.D.3d 991, 992-93 [N.Y. App. Div., 3d Dep’t 2007]), it is vulnerable to a motion by the defendant to dismiss under Rule 3211(a)(7) of the CPLR for its failure to state a cause of action (e.g., Willis v. Kepner, 109 A.D.2d 950, 951 [N.Y. App. Div., 3d Dep’t 1985]). Why should any plaintiff’s attorney take the risk of a dismissal, if information is available for conscientiously alleging facts addressing each necessary element?  And if an element cannot be ethically alleged, the cause of action should not be asserted in the first place.

Defense attorneys wear a different hat.  The elements of the cause of action should be closely examined to assure that the complaint states a compensable claim.  Defense counsel must consider each defense that might be available to those elements --- for defamation, for example, truth of the statement, or its lack of publication to a third person.  Each defense should be asserted as a separate affirmative defense per Section 3018(b) of the CPLR to preserve its grounds, prevent later surprise to the adverse party, and permit the assertion of those defenses at the trial.  Defense attorneys must guard against the failure to assert a viable affirmative defense.  That is underscored by Rule 3211(e) of the CPLR, which enumerates various affirmative defenses which are waived if not affirmatively pleaded in the answer (CPLR 3211[e]).  Avoid that nightmarish conversation with the client where you might have to say “Yes, you have a great defense, but I failed to allege it as an affirmative defense in your answer two years ago, and we can’t raise it now since the trial is this Monday.  My bad.”  

There is a peculiar difference in how to respond to counterclaims and cross-claims.  Counterclaims absolutely require a responsive “Reply” (CPLR § 3011), which is an answer by a different title.  Cross-claims, by contrast, are “deemed denied” if not answered, unless the cross-claim specifically demands an answer to it (CPLR § 3011), in which case the responding party must serve an answer to avoid a pleading default (CPLR § 3011; Giglio v. NTIMP, 86 A.D.3d 301 [N.Y. App. Div., 2d Dep’t 2011]).  Beware of those distinctions.  Parties serving cross-claims have no downside to demanding an answer to it, and responding parties are off the hook absent such a demand.  But if the demand for an answer is made within the cross-claim, pay attention to it and answer it accordingly.
Be mindful of the need for verifying the pleading.  When a pleading is verified, each responsive pleading shall be verified as well, except for the answer of infants or for matters subject to a privilege (CPLR § 3020[a]).  
Some forms of pleadings require particularity.  Rule  3015 of the CPLR demands particularity for certain matters such as the performance of conditions precedent, corporate status, and the licensure to business with consumers in the counties of Long Island, New York City, Westchester, Rockland, and Putnam Counties (CPLR 3015[a], [b], [c]).  Specific types of claims must be pleaded with particularity including but not limited to defamation, fraud or mistake, separation or divorce, the applicability of the law of a foreign country, the existence of a threshold injury in automobile-related personal injury actions, and the itemization of labor, material and services in claims involving the sale or delivery of goods and services (CPLR 3016[a], [b], [c], [e], [f], and [g]).  Pleadings which fail to contain the requisite particularity, where required, are subject to dismissal pursuant to Rule 3211(a) of the CPLR.

Punitive damages are not to be pleaded as a free-standing cause of action but are instead a prayer for relief to be included within the Wherefore clause (Pisula v. Roman Catholic Archdiocese of New York, 201 A.D.3d 88, 102 [N.Y. App. Div., 2d Dep’t 2021]).

As for ad damnum clauses, relief shall be demanded absolutely or in the alternative (CPLR § 3017[a]).  The demand for damages helps assure that the action is within monetary jurisdictional limits of the court of commencement.  However, in actions involving personal injury or wrongful death, there shall only be a prayer for general relief (e.g., “money damages”) which is intended to curb exaggerated demands (Braun v. Ahmed, 127 A.D.2d 418, 428 [N.Y. App. Div., 2d Dep’t 1987]), unless the answering party requests a supplemental demand requesting the total actual amount of damages that the claimant seeks (CPLR § 3017[c]).  There is no downside for answering parties to make such a request, as knowing the specific amount of a demand can help define the seriousness of the action, aid settlement in certain instances, and determine whether an action falls within the scope of the responding party’s general and excess insurance coverages.  Actions for declaratory judgments should specify the declaration of rights that is requested, along with any further or consequential relief that may be claimed and its nature and extent [CPLR § 3017[b]).  On this point, a motion to dismiss a declaratory judgment action presents only the issue of whether a cause of action for declaratory relief is set forth, and not necessarily whether the plaintiff is entitled to a favorable declaration (Jacobs v. Cartalemi, 156 A.D.3d 635, 637 [N.Y. App. Div., 2d Dep’t 2017], lv. to appeal denied 32 N.Y.3d 903 [2018]).    

Happy pleading.

Hon. Mark C. Dillon is a Justice of the Appellate Division, Second Department, an Adjunct Professor of New York Practice at Fordham Law School, and a contributing author of CPLR Practice Commentaries in McKinney’s.