Courts seem to scrutinize the question of damages to a higher degree in legal malpractice litigation.  Break a leg in a slip and fall, and the Court will never review an x-ray on a motion for summary judgment; have a car crash and no court will call in the body-shop guy on the question of whether there was really damage to the bumper.  However in Legal Malpractice, there will be extensive review of actual v. ascertainable damages.  In Fielding v Kupferman 2011 NY Slip Op 31983(U) ;July 12, 2011;Supreme Court, : 113572/07;Judge: Eileen A. Rakower we see one such example. After analysis, and a motion to reargue, summary judgment is granted to defendants.
 

"This action, sounding in attorney malpractice, arises from a stipulation of settlement in a divorce action, wherein defendants represented plaintiff. Specifically, the alleged malpractice involves defendants advising plaintiff to sign the settlement agreement, which required that a 1.2 million dollar payment be made “within 30 days after the execution [of the stipulation of settlement] . . . in
immediately available funds.” Plaintiff claims that funds were not immediately available, as stated, and he failed to make payment as required. Plaintiff brought this action, and defendants moved to dismiss. The Appellate Division, reversing Justice Walter Tolub’s dismissal, found that, accepting plaintiffs allegations as true, the stipulation may constitute evidence of defendants’ negligence. Further, “a pleading need only state allegations from which damages attributable to the
defendant’s conduct may reasonably be inferred.” They went on to say that “at this early stage of the proceedings, plaintiff is not obliged to show that he actually sustained damages, but only that damages attributable to defendants’ conduct might be reasonably inferred.”

"Defendants later moved for summary judgment dismissing this action as against them. Defendants urged that any damages were pure speculation, and that plaintiff could not sustain his burden of showing, by proof in admissible form, that he suffered non speculative and ascertainable damages as a result of entering into  the stipulation of settlement which required that payment be made within 30 days in immediately available funds. This Court, after oral argument and by Decision and Order dated December 14,20 10, denied the motion. That decision is currently on appeal. Defendants now move to reargue. Defendants’ motion to reargue is granted and, upon reargument, defendants’ motion for summary judgment is granted."
 

"Finally, the question turns to whether plaintiff has shown “actual damages.” Assuming a jury were to find that the attorney negligence was the proximate cause of sending plaintiff through the many hoops he claims he had to jump through in order to meet his responsibility of paying approximately 1.2 million dollars within 30 days, the question remains, did plaintiff show that he suffered actual damages. Plaintiff claims that even if he suffered nominal damages, a finding in his favor would require defendants to disgorge back to plaintiff all of the fees they charged in representing plaintiff in his divorce action. "