Too speculative is a defense commonly utilized by defendants in legal malpractice settings.  Here, in Birch v Novick & Assoc., P.C.   
2019 NY Slip Op 31712(U) June 14, 2019 Supreme Court, New York County Docket Number: 161445/13, Justice Carol R. Edmead discusses just how speculative they might be.

“Defendants argue that the complaint must be dismissed, as Plaintiff has not sustained any ascertainable damages. Weinblatt, one of the attorney’s Plaintiff hired after losing confidence in
Defendants, who is also a CPA, sent Plaintiff an email on November 21, 2012, stating that her share of her residuary estate, “based upon [Kappenberg] receiving no elective share” was “$1,800, 709 .11 “4 Plaintiff submits no competing computation of what Plaintiff would have been awarded if she successfully challenged Kappenberg’ s right of election.

Since Plaintiff ultimately received $2.3 in the settlement, Defendants argue that she cannot show actual damages. Hochberg_, Defendants’ counsel, opines: “Plaintiff received a surplus of approximately $500,000 as a result of the efforts of (Defendants] and co-counsel .. I am advised that … Plaintiff seeks … to recover legal fees she paid in the amount of $331,699.59 …. [T]aking Plaintiff’s claims at face value, the extra $500,00 [Defendants] obtained for Plaintiff more
than offsets the totality of the legal fees paid by the Plaintiff concerning the Underlying Matter” (NYSCEF doc No. 25-27).

Plaintiff, in opposition, argues that the 1.8 million estimate does not take into account the residual right that Plaintiff would have had in the $2.1 million trust in Kappen berg’s benefit provided for in the 2008 Will. Defendants, in reply, argue that the hypothetical worth of this residual right is impertnissibly speculative and”that Plaintiff waived her claim to any damages related to the residual right by not including it from its second amended damages chart.

Generally, a plaintiff in a legal malpractice action can recover for damages it expended – mitigating the damage of an attorney’s negligence (Kagan Lubic Lepper Finklestein & Gold v 325 Fifth Ave. Condominium, 2015 NY Slip Op. 31470[U] [Sup Ct, NY County, Kern, J][cognizable damages in a legal malpractice action include consequential damages sustained as a result of the attorney’s malpractice, including expenses such as experts fees and attorney’s fees”]). Here; as there are questions of fact relating to negligence, there are concomitant questions of fact related to consequential damages arising from the alleged negligence. That is, a factfinder could find that Defendants were negligent and that Plaintiff expended additional fees to remedy that negligence. In other words, a factfinder could find that, absent negligence, Plaintiff could have attained the $2.3 settlement without having to hire additional attorneys.

Moreover, it would it would be error for the court to determine that Plaintiff could not establish damages based on Weinblatt’s estimate as to the amount Plaintiff would have received under the 2008 Will and the $2.3 million Plaintiffinherited under the settlement. While Defendants argue that Plaintiffs residual right tO’the Kappenberg trust provided for in the 2008 Will is too speculative to serve as a Qasis to deny summary judgment, the estimate that Defendants rely on is also, fundamentally, speculative. Moreover, the question of whether Plaintiff waived any damages claim based on this residual right is a question best reserved for the factfinder. As questions of fact as to damages remain, the branch of Defendants’ motion that seeks dismissal of the complaint as Plaintiff cannot show actual damages must be denied.  “