Roland Machinery Co. v. Dresser Industries, Inc., 749 F.2d 380, 386 (7th Cir. 1984) (noting absence of an adequate remedy at law is a precondition to any form of equitable relief, but such ultimate relief can easily wait until the end of trial, only if a movant "will suffer irreparable harm—that is, harm that cannot be prevented or fully rectified by the final judgment after trial—can he get a preliminary injunction.") A judgment on the merits is required prior to the issuance of a decree of specific performance, whereas "the issuance of a preliminary injunction is procedurally truncated, occurring prior to judgment on the merits, and, for that reason, it is an extraordinary remedy requiring both the absence of adequate remedy at law and the clear establishment of the burden of persuasion as to each of the four prerequisites." Great Am. Ins. Co. v. Fountain Eng'g, Inc, No. 15-CIV-10068-JLK, 2015 WL 6395283, at *2 (S.D. Fla. Oct. 22, 2015). "While a surety need not sustain a loss from its own pocket before it can raise a claim demanding specific enforcement of an indemnity agreement, the fact that the claim exists does not establish irreparable injury for purposes of injunctive relief."

It's true that "a delay in bringing suit may defeat a presumption of irreparable harm." Great Am. Ins. Co. v. Fountain Eng'g, Inc., 2015 WL 6395283, at *4 (S.D. Fla. Oct. 22, 2015). But Plaintiff previously sued GDC officials because they refused to restart her HRT or evaluate her for gender-affirming surgery.

. between the ordinary remedy of specific performance and the extraordinary remedy of a preliminary injunction; to find otherwise would be to create a per se rule that would eliminate the crucial . . . test for preliminary injunctions, in such cases where specifically enforceable contractual provision are at issue.” Great Am. Ins. Co. v. Fountain Eng'g, Inc., No. 15-CIV-10068, 2015 WL 6395283, at *2 (S.D. Fla. Oct. 22, 2015) (King, J.) (quoting Firemen's Ins. Co. of Newark, N.J. v. Keating, 753 F.Supp. 1146, 1151 (S.D.N.Y. 1990) (internal quotations omitted)).

. between the ordinary remedy of specific performance and the extraordinary remedy of a preliminary injunction; to find otherwise would be to create a per se rule that would eliminate the crucial . . . test for preliminary injunctions, in such cases where specifically enforceable contractual provision are at issue.” Great Am. Ins. Co. v. Fountain Eng'g, Inc., No. 15-CIV-10068, 2015 WL 6395283, at *2 (S.D. Fla. Oct. 22, 2015) (King, J.) (quoting Firemen's Ins. Co. of Newark, N.J. v. Keating, 753 F.Supp. 1146, 1151 (S.D.N.Y. 1990) (internal quotations omitted)).

Delay in seeking enforcement of those rights, however, tends to indicate at least a reduced need for such drastic speedy action.'” Great Am. Ins. Co. v. Fountain Eng'g, Inc., No. 15-CIV-10068-JLK, 2015 WL 6395283, at *4 (S.D. Fla. Oct. 22, 2015) (quoting Citibank, N.A. v. Citytrust, 756 F.2d 273, 276 (2d Cir. 1985) and collecting other cases). In the instant case, Plaintiffs filed suit in January 2020 (DE 1) and then filed their Motion for PI in June 2021 (DE 95), after they filed a motion for partial summary judgment (DE 86).

Delay in seeking enforcement of those rights, however, tends to indicate at least a reduced need for such drastic speedy action.'" Great Am. Ins. Co. v. Fountain Eng'g, Inc., No. 15-CIV-10068-JLK, 2015 WL 6395283, at *4 (S.D. Fla. Oct. 22, 2015) (quoting Citibank, N.A. v. Citytrust, 756 F.2d 273, 276 (2d Cir. 1985) and collecting other cases). In other words, a plaintiff seeking a significant extension of time for the Court to rule on preliminary injunctive relief "cuts against the factor of irreparable harm . . . [for] the extraordinary and drastic remedy."

The showing of irreparable harm is "[p]erhaps the single most important prerequisite for the issuance of a preliminary injunction ... that if ... not granted the applicant is likely to suffer irreparable harm before a decision on the merits can be rendered." Great Am. Ins. Co. v. Fountain Eng'g, Inc. , No. 15-CIV-10068-JLK, 2015 WL 6395283, at *3 (S.D. Fla. Oct. 22, 2015). In addition, the asserted irreparable harm must be "neither remote nor speculative, but actual and imminent."

" ‘[T]he fact that plaintiff may, in the interim, be marginally less secure with respect to the availability of a final money judgment [or decree], does not constitute "irreparable harm" so as to warrant the extraordinary remedy of a preliminary injunction.’ " Great Am. Ins. Co. v. Fountain Eng'g, Inc. , No. 15-CIV-10068-JLK, 2015 WL 6395283, at *3 (S.D. Fla. Oct. 22, 2015) (quoting Firemen's Ins. Co. v. Keating , 753 F.Supp. 1146, 1157 (S.D.N.Y. 1990) ). The purpose of a collateral security clause is to provide sureties with access to financial cushioning during the pendency of claims and, where violated, the surety suffers ongoing harm in the form of missing money, but, whatever the loss, whether to financial security or otherwise, it is monetary in character, and may be adequately remedied by a judgment on the merits.

"[I]t is settled law that '[a]n injury is 'irreparable' only if it cannot be undone through monetary remedies.'" Great Am. Ins. Co. v. Fountain Eng'g, Inc, No. 15-10068, 2015 WL 6395283, at *3 (S.D. Fla. Oct. 22, 2015) (quoting Snook v. Trust Co. of Ga. Bank of Savannah, N.A., 909 F.2d 480, 487 (11th Cir. 1990)); accord Roland Mach. Co. v. Dresser Indus., Inc., 479 F.2d 380, 386 (7th Cir. 1984) ("The requirement of irreparable harm is needed to take care of the case where although the ultimate relief that the plaintiff is seeking is equitable . . . he can easily wait till the end of trial to get that relief. Only if he will suffer irreparable harm—that is, harm that cannot be prevented or fully rectified by the final judgment after trial—can he get a preliminary injunction."), quoted in Great Am. Ins. Co., 2015 WL 6395283, at *2 n.2.

As the Indemnitors point out, some courts have held that a violation of a collateral-security provision does not necessarily result in irreparable harm. See Great Am. Ins. Co. v. Fountain Eng'g, Inc., No. 15-CIV-10068-JLK, 2015 WL 6395283, at *3-*4 (S.D. Fla. Oct. 22, 2015) (unpublished); Westchester Fire Ins. Co. v. DeNovo Constructors, Inc., No. 15-CV-7940 (AJN), 2016 WL 1381821, at *2 (S.D.N.Y. Apr. 5, 2016). One court has reasoned,