(1) whether the improper conduct was willful, or negligent; (2) whether it was part of a pattern o[f] activity, or an isolated event; (3) whether it infected the entire pleading, or only one particular count or defense; (4) whether the person has engaged in similar conduct in other litigation; (5) what effect it had on the litigation process in time or expense; (6) whether the responsible person is trained in the law; [and] (7) what amount, given the financial resources of the responsible person, is needed to deter that person from repetition in the same case. Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16-CV-885 (JPO), 2019 WL 422613, at *3 (S.D.N.Y. Feb. 4, 2019). If “the court determines that Rule 11(b) has been violated, the court may impose an appropriate sanction on any attorney, law firm, or party that violated the rule or is responsible for the violation.”

To grant a motion for sanctions under Rule 11(c)(2), the Court must find, in addition to the satisfaction of the “safe harbor” requirement, that the complained of conduct was “objective[ly] unreasonable[]....” Storey v. Cello Holdings, L.L.C., 347 F.3d 370, 387 (2d Cir. 2003) (quoting Margo v. Weiss, 213 F.3d 55, 65 (2d Cir. 2000)). “[I]f the district court concludes that the assertion of a given claim violates Rule 11 . . . the decision whether or not to impose sanctions is a matter for the court's discretion.” Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16-cv-885, 2019 WL 422613, at *2 (S.D.N.Y. Feb. 4, 2019) (citing Perez v. Posse Comitatus, 373 F.3d 321, 325 (2d Cir. 2004)). Courts maintain a “high bar” for establishing a Rule 11 violation given judicial concern for encouraging “zealous advocacy.”

Finally, although the Court's prior order did not identify Rule 11 as a potential basis for sanctions, even if the Court were to find that the statements in Defendant Azizo's declaration violated Rule 11, “the decision whether or not to impose sanctions is a matter for the court's discretion.” Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16-cv-885, 2019 WL 422613, at *2 (S.D.N.Y. Feb. 4, 2019) (declining to impose Rule 11 sanctions).

Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16-CV-885, 2019 WL 422613, at *3 (S.D.N.Y. Feb. 4, 2019) (citing Continental Casualty Co. v. Marshall Granger & Co., No. 11-CV-3979, 2017 WL 1901969, at *7 (S.D.N.Y. May 9, 2017)) (internal alteration and additional citation omitted). When fashioning a sanction, “courts must remain mindful that the point of Rule 11 sanctions is not to compensate or reimburse the defendants for the totality of their losses, but rather to punish and to deter future similar conduct.”

. "[P]f the district court concludes that the assertion of a given claim violates Rule 11 . . . the decision whether or not to impose sanctions is a matter for the court's discretion." Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16-cv-885, 2019 WL 422613, at *2 (S.D.N.Y. Feb. 4, 2019) (citing Perez v. Posse Comitatus, 373 F.3d 321, 325 (2d Cir. 2004)).

“Rule 11(b)(2) establishes an objective standard of reasonableness for determining whether counsel is presenting a frivolous argument.” Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16 Civ. 885 (JPO), 2019 WL 422613, at *2 (S.D.N.Y. Feb. 4, 2019) (internal quotation marks omitted); see Simon DeBartolo Grp. v. Richard E. Jacobs Grp., 186 F.3d 157, 166 (2d Cir. 1999). “The appropriateness of sanctions is distinct from the underlying merits of a claim.”

"[I]f the district court concludes that the assertion of a given claim violates Rule 11 . . . the decision whether or not to impose sanctions is a matter for the court's discretion." Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16-CV-885 (JPO), 2019 WL 422613, at *2 (S.D.N.Y. Feb. 4, 2019). However, any sanction "must be limited to what suffices to deter repetition of the conduct or comparable conduct by others similarly situated."

If a court determines that Rule 11(b) has been violated, the decision whether or not to impose sanctions is ultimately "a matter for the court's discretion." Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16-CV-885, 2019 WL 422613, at *2 (S.D.N.Y. Feb. 4, 2019) (internal citation omitted). The Court need not spend much time dispensing with Quarters' first argument, as the Court would not have denied Quarters' motion to dismiss had it concluded that Plaintiffs' arguments were baseless.

the decision whether or not to impose sanctions is a matter for the court's discretion.'” Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16-CV-885 (JPO), 2019 WL 422613, at *2 (S.D.N.Y. Feb. 4, 2019) (alterations in original) (quoting Perez v. Posse Comitatus, 373 F.3d 321, 325 (2d Cir. 2004)). “When divining the point at which an argument turns from merely losing to losing and sanctionable, ” courts must “resolve all doubts in favor of the signer” of the pleading.

Nevertheless, "[e]ven if the district court concludes that the assertion of a given claim violates Rule 11 . . . the decision whether or not to impose sanctions is a matter for the court's discretion." Bobcar Media, LLC v. Aardvark Event Logistics, Inc., No. 16-CV-885 (JPO), 2019 WL 422613, at *2 (S.D.N.Y. Feb. 4, 2019). The appropriateness of sanctions is distinct from the underlying merits of a claim.