NORTHFIELD INSURANCE COMPANY v. TAFF MANAGEMENT CORP (2026)

ORDER GRANTING PLAINTIFF'S MOTION FOR SUMMARY JUDGMENT

THIS CAUSE is before the Court upon Plaintiff Northfield Insurance Company's (“Northfield”) Motion for Summary Final Judgment [ECF Nos. 63] (the “Motion”), filed on February 26, 2026, seeking a declaratory judgment that Northfield has no duties to defend or indemnify Defendants Taff Management Corporation d/b/a Ocean Manor Resort (“Taff Management”) and/or David Brasher (“Brasher”). Taff Management has responded in opposition [ECF No. 67], and Plaintiff has replied [ECF No. 69]. Pro se Defendant Brasher failed to respond by the June 30, 2026, deadline, as ordered by the Court on April 27, 2026. [See ECF No. 70]. The Motion is, therefore, ripe for resolution. Upon due consideration of the Motion, the parties’ parties, the record and governing law, the Motion is GRANTED for the reasons discussed below.

I. PROCEDURAL HISTORY

Northfield filed a Complaint for declaratory relief on August 1, 2025. [Compl., ECF No. 1]. At that time, Northfield sought declaratory judgment against Defendants Taff Management, Brasher, Ocean Manor Condominium Association, and Carl Jordan Failla (as personal representative of the Estate of Carl Jospeh Failla and guardian of the property of Joan Failla). [See id. at 1]. On September 19, 2025, Taff Management answered the Complaint. [ECF No. 22].

On September 24, 2025, Northfield filed an Amended Complaint [FAC, ECF No. 25], seeking declaratory relief against Taff Management, Brasher, Galt Ocean Manor Condominium Association (“Galt”), and Carl Jordan Failla (as personal representative of the Estate of Carl Jospeh Failla and guardian of the property of Joan Failla). [See id. at 1]. Carl Jordan Failla and Galt each answered the Amended Complaint. [ECF Nos. 32, 35]. Jordan Failla and Galt were subsequently dismissed from this action by stipulation. [ECF No. 40, 47].

Taff Management did not respond to the Amended Complaint, and Brasher failed to plead or otherwise respond at all in this case. [See ECF No. 37 (Clerk's Entry of Default against Brasher)]. Those failures have consequences at summary judgment. Federal Rule of Civil Procedure 8 provides in relevant part:

A party that intends in good faith to deny all the allegations of a pleading—including the jurisdictional grounds—may do so by a general denial. A party that does not intend to deny all the allegations must either specifically deny designated allegations or generally deny all except those specifically admitted.

Fed. R. Civ. P. 8(b)(3). Additionally, Rule 8 provides that “[a] party that intends in good faith to deny only part of an allegation must admit the part that is true and deny the rest.” Fed. R. Civ. P. 8(b)(4). “An allegation—other than one relating to the amount of damages—is admitted if a responsive pleading is required and the allegation is not denied.” Fed. R. Civ. P. 8(b)(6). As a “general rule,” a party “is bound by the admissions in his pleadings.” Best Canvas Prods. & Supplies, Inc. v. Ploof Truck Lines, Inc., 713 F.2d 618, 621 (11th Cir. 1983) (affirming grant of summary judgment that bound non-moving party to admissions made in pleadings). Admissions in pleadings are judicially admitted facts that are “established not only beyond the need of evidence to prove them, but beyond the power of evidence to controvert them.” Cooper v. Meridian Yachts, Ltd., 575 F.3d 1151, 1178 (11th Cir. 2009) (quoting Hill v. Fed. Trade Comm'n, 124 F.2d 104, 106 (5th Cir. 1941)).

That means all well-pleaded allegations in the Amended Complaint are deemed admitted by Brasher. As for Taff Management, any additional allegations pleaded in the Amended Complaint not pleaded in the original complaint are deemed admitted against Taff Management. See LaGorga v. Kroger Co., 407 F.2d 671 (3rd Cir. 1969).

II. LEGAL STANDARD

Summary judgment is appropriate “if the movant shows that there is no genuine dispute as to any material fact and the movant is entitled to judgment as a matter of law.” Fed. R. Civ. P. 56(a). A properly supported motion for summary judgment is only defeated by the existence of a genuine issue of material fact. Anderson v. Liberty Lobby, Inc., 477 U.S. 242, 249, 106 S.Ct. 2505, 91 L.Ed.2d 202 (1986). The moving party bears the initial burden of showing that there are no genuine issues of material fact. Hickson Corp. v. N. Crossarm Co., 357 F.3d 1256, 1260 (11th Cir. 2004). When the moving party has discharged its burden, the nonmoving party must then designate specific facts showing the existence of genuine issues of material fact. Jeffery v. Sarasota White Sox, Inc., 64 F.3d 590, 593-94 (11th Cir. 1995). If there is a conflict between the parties’ allegations or evidence, the nonmoving party's evidence is presumed to be true and all reasonable inferences must be drawn in the nonmoving party's favor. Shotz v. City of Plantation, 344 F.3d 1161, 1164 (11th Cir. 2003). “Summary judgment is appropriate in declaratory judgment actions seeking a declaration of coverage when the insurer's duty, if any, rests solely on the applicability of the insurance policy, the construction and effect of which is a matter of law.” Joynt v. Star Ins. Co., 314 F. Supp. 3d 1233, 1237 (M.D. Fla. 2018) (citing Ernie Haire Ford, Inc. v. Universal Underwriters Ins. Co., 541 F. Supp. 2d 1295, 1297 (M.D. Fla. 2008)).

III. BACKGROUND FACTS

Northfield seeks a declaration that it has no obligation to defend or indemnify Taff Management and/or Brasher in an underlying lawsuit filed by Carl Jordan Failla (“Jordan”) as Personal Representative of the Estate of Carl Joseph Failla (“Joseph”) and as Guardian of the Property of Joan Failla (“Joan”). [See Compl., ECF No. 1-1, Failla v. Brasher and Taff Mgmt., Case No. CACE-25-002641 (03) (11th Jud. Cir., Broward Cnty., Fla.)]. In the state-court lawsuit, Jordan alleges his father Joseph was walking across a pedestrian crosswalk at the intersection of A1A North Ocean Blvd. and N.E. 36th Street in Fort Lauderdale, Florida when he was struck and killed by a motor vehicle (2020 Jeep) driven by Brasher, who was acting within the course of his employment with Taff Management at the time. [FAC, ECF No. 25 ¶¶ 13–21]. According to the traffic homicide investigation, Taff Management had directed Brasher to move his vehicle from a hotel parking lot to another location to accommodate hotel guests at the time Joseph was struck and killed. [PSOMF ¶ 7]. On those allegations, Jordan asserted a wrongful death claim against Brasher and a vicarious liability claim against Taff Management, seeking the recovery of damages and costs from both defendants. [ECF No. 1-1 at 4–7, Failla v. Brasher and Taff Mgmt., Case No. CACE-25-002641 (03) (11th Jud. Cir., Broward Cnty., Fla.)].

Relevant to this litigation, Taff Management was insured by Northfield under Commercial Insurance Policy WS553866 (the “Policy”) at the time Brasher struck Joseph with his Jeep, killing him. [See FAC, ECF No. 25 ¶ 22–26; ECF No. 25-2]. The Policy provides for general bodily injury and property damage which states, in relevant part, as follows:

We will pay those sums that the insured becomes legally obligated to pay as damages because of “bodily injury” or “property damage” to which this insurance policy applies. We will have the right and duty to defend the insured against any “suit” seeking those damages. However, we will have no duty to defend the insured against any “suit” seeking damages for “bodily injury” or “property damage” to which this insurance does not apply․

[ECF No. 25-2 at 24, Policy Sec. 1.1.a. (Coverages)].

The Policy covers Taff Management employees like Brasher “for acts within the scope of their employment․ while performing duties related to the conduct of [Taff Management's] business.” [ECF No. 25-2 at 32, Policy Sec. 2.a. (Who Is An Insured).]. The Policy also contains an endorsement that specifically excludes coverage for “ ‘bodily injury’ or ‘property damage’ arising out of the ․use ․ of any ‘auto’ ․ owned or operated by ․ any insured․ This exclusion applies even if the claims against any insured allege negligence or other wrongdoing in the supervision, hiring, employment, training or monitoring of others by that insured, if the ‘occurrence’ which caused the ‘bodily injury’ or ‘property damage’ involved the ․ use․ of any ‘auto’․ that is owned or operated by ․ any insured.” [ECF No. 25-2 at 24, Policy Sec. 1.2.g. (Exclusions)].

IV. DISCUSSION

At summary judgment, Northfield argues entitlement to judgment as a matter of law on its obligations to defend and indemnify Taff Management and/or Brasher for the claims asserted against them in the underlying lawsuit because those claims are expressly excluded under the Policy's “auto” endorsement. [ECF No. 63]. Taff Management opposes summary judgment on the grounds that, if Taff Management's pending state-court motion for summary judgment is resolved in Taff Management's favor, the Northfield's Motion in this case will be rendered moot. [ECF No. 67]. Apart from the irrelevance of this argument, the outstanding issue at summary judgment in the underlying lawsuit is whether Brasher was acting within the scope of his employment at the time of the fatal accident. See Failla v. Brasher and Taff Mgmt., Case No. CACE-25-002641 (03) (11th Jud. Cir., Broward Cnty., Fla.). Whether that issue is resolved in Taff Management's favor or not, the claims asserted in the underlying case are clearly not covered under the express terms of the Policy, which is what matters here.

Taff Management advances two very weak reasons for denying summary judgment considering the clear exclusion under the terms of the Policy. [See ECF No. 67]. First, Taff Management contends the Court cannot grant summary final judgment on Northfield's declaratory judgment claims without Northfield's having addressed Defendants’ affirmative defenses. [Id. at 2–3 (citing Stillman v. Travelers Ins. Co., 88 F.3d 911, 913 (11th Cir. 1996)) (reversing summary judgment for plaintiff in insurance coverage dispute because the plaintiff's “motion for summary judgment did not address [affirmative defenses] raised by [the insured], nor did [the plaintiff] offer any evidence of undisputed facts as to these defenses, as required by Fed R. Civ. P. 56(c)”); State Farm Mut. Aut. Ins. Co. v. Physicians Injury Care Center, Inc., No. 6:06-cv-1757-Orl-GJK, 2008 WL 11337326, at *3 (M.D.Fla. Dec. 18, 2008) (“[a] plaintiff must address the undisputed facts regarding affirmative defenses asserted in the defendant's answer, and a failure to do so should result in denial of the motion for summary judgment.”)]. Second, Taff Management attempts to invoke the doctrine of equitable estoppel, contending the doctrine prevents Northfield from withdrawing its defense of the state-court action before that court resolves Taff Management's pending motion for summary judgment. [Id. at 3–5]. Although hard to follow, Taff Management says this Court's adjudicating the Northfield's Motion for Summary Judgment would be “tantamount to an advisory opinion” were this Court to rule before the state court resolves Taff's Management's motion for summary judgment (which if resolved in Taff's favor, would “moot” the Motion before this Court). [Id.].

Northfield's reply is three-fold. First, Northfield argues Taff Management is really seeking a stay of this action without making the requisite showing. [ECF No. 69 at 3–4]. Second, with respect to Defendants’ affirmative-defenses argument, Northfield contends it has either addressed Northfield's defenses, or the defenses themselves are legally insufficient. [ECF No. 69 at 5–6]. Third, as for collateral estoppel, Northfield maintains that argument fails as a matter of law. [Id. at 6–7 (citing Scottsdale Ins. Co. v. Outrigger Beach Club Condo. Ass'n, 304 F. Supp. 3d 1208, 1215 (M.D. Fla. 2018)) (citing Doe v. Allstate Ins. Co., 653 So. 2d 371, 373 (Fla. 1995))]. Northfield points out that Taff's estoppel argument is

premised on a legally incorrect proposition, that Northfield's provision of a defense precludes it from seeking a declaration regarding coverage. Florida law is clear that the opposite is true. Because Northfield issued a reservation of rights and has at all times acted within its rights under the policy and applicable law, estoppel does not apply and does not bar the relief sought by Northfield in its Motion for Final Summary Judgment.

[ECF No. 69 at 7].

The Court first addresses the elephant in the room—Taff Management's utter failure to address the substance of Northfield's Motion.

A. Defendants’ failure to address the merits of Northfield's Motion.

For starters, Defendants waived opposition to the enforcement of the Policy's “auto” endorsement by failing to respond to Northfield's motion on the merits. See Wilkerson v. Grinnell Corp., 270 F.3d 1314, 1322 (11th Cir. 2001) (finding opposition abandoned when argument not presented in response to motion for summary judgment). In its Motion, Northfield carefully explained why, under each of the applicable Policy provisions, summary judgment is appropriate in its favor. [See ECF No. 63]. In opposition, Taff Management does not contest that the Policy provisions cited by Northfield apply, nor does it cite to any other Policy provision which provides coverage notwithstanding the “auto” endorsement. [See generally, ECF No. 67]. Brasher has not responded at all.

Tellingly, Taff Management also concedes it “is not arguing that Northfield is not entitled to declaratory relief at all.” [Id. at 5]. Instead, Taff Management merely posits that ruling on Northfield's Motion prior to the state court's resolution of Taff Management's motion for summary judgment would waste the parties’ and the Court's resources. [Id.]. Taff Management cites no authority for this proposition, however. And, the law is quite clear the other way around. “[A]llowing ‘a declaratory action by an insurer to establish nonliability under casualty insurance was one of the prime purposes of the Declaratory Judgment Act.’ ” James River Ins. Co. v. Rich Bon Corp., 34 F.4th 1054, 1062 (11th Cir. 2022) (Brasher, J., concurring) (quoting Nat'l Trust Ins. Co. v. S. Heating & Cooling, Inc., 12 F.4th 1278 (11th Cir. 2021) (Brasher, J., concurrence)).

In sum, Defendants’ failures to (1) address the merits of the instant Motion or (2) cite any legal basis whereby the Court must delay its declaration of the rights and obligations of the parties as authorized by Congress and requested by Northfield, are fatal to its opposition.

B. The claims asserted in the underlying action are not covered by the Policy.

Additionally, Northfield is entitled to judgment as a matter of law on the merits. A court may grant summary judgment “ ‘in declaratory judgment actions seeking a declaration [as to insurance coverage] when the insurer's duty, if any, rests solely on the applicability of the insurance policy, the construction and effect of which is a matter of law.’ ” TIG Ins. Co. v. Smart Sch., 401 F. Supp. 2d 1334, 1337 (S.D. Fla. 2005) (quoting Northland Cas. Co. v. HBE Corp., 160 F. Supp. 2d 1348, 1358 (M.D. Fla. 2001)). “In a declaratory judgment action, ‘if the allegations in the complaint alleging a claim against the insured either are acts not covered by the policy or are excluded from the policy's coverage, the insurer is not obligated to defend or indemnify.’ ” Id. (quoting Northland, 160 F. Supp. 2d at 1357–58).

Under Florida law, an insurance policy is treated like a contract, and as such, ordinary contract construction and interpretation principles apply. See id. at 1342. The language and terms of the insurance policy define the scope and extent of coverage. See id. If the language is unambiguous, the policy must be enforced as written. See Siegle v. Progressive Consumers Ins. Co., 819 So. 2d 732, 734–35 (Fla. 2002). If a policy is “ ‘susceptible to more than one reasonable interpretation, one providing coverage and the other limiting coverage,’ ” ambiguities should be resolved in favor of the insured. Travelers Indem. Co. v. PCR Inc., 889 So. 2d 779, 785–86 (Fla. 2004) (quoting Swire Pac. Holdings, Inc. v. Zurich Ins. Co., 845 So. 2d 161, 165 (Fla. 2003)). Clauses providing coverage are interpreted broadly to effect the greatest amount of coverage within the policy's limits. Westmoreland v. Lumbermens Mut. Cas. Ins. Co., 704 So. 2d 176, 179 (Fla. Dist. Ct. App. 1997). On the other hand, exclusionary clauses are strictly construed. See State Farm Fire & Cas. Co. v. CTC Dev. Corp., 720 So. 2d 1072, 1076 (Fla. 1998). While exclusionary clauses cannot be relied on to create coverage, an insurance policy should be read in “the entirety of its terms and conditions.” Id. at 1075; see also Fla. Stat. § 627.419(1). But, the “terms of an insurance policy should be taken and understood in their ordinary sense and the policy should receive a reasonable, practical and sensible interpretation consistent with the intent of the parties—not a strained, forced or unrealistic construction.” Siegle, 819 So. 2d at 736 (citation and internal quotation marks omitted).

This case involves straightforward contract interpretation. The Policy excludes coverage for bodily injury or property damage arising out of an insured's use of an automobile. It is undisputed that Joseph Failla's fatal injuries arose from Brasher's use of an automobile and that Brasher is considered an insured under the Policy. Thus, for purposes of this case, it does not matter whether Brasher was acting within (or outside of) the scope of his employment with Taff Management at the time he struck and killed Joseph. See, e.g., First Mercury Ins. Co. v. Sudderth, 620 F. App'x 826, 828–30 (11th Cir. 2015); Burlington Ins. Co. v. Normandy Gen. Ptnrs., 560 F. App'x 844, 848 (11th Cir. 2014); Hudson Excess Ins. Co. v. Sudo Bar & Grill, LLC, No. 1:23-CV-00462-ELR, 2025 WL 2889205, at *6 (N.D. Ga. Apr. 30, 2025) (concluding “as a matter of law, the underlying suits’ allegations do not constitute a covered loss under the Policy, and thus neither the duty to defend nor the duty to indemnify is triggered”) (citing Nat'l Cas. Co. v. Pickens, 582 F. App'x 839, 841 (11th Cir. 2014)) (“If there is no duty to defend, there is no duty to indemnify.”). Accordingly, Northfield has no duty to defend or indemnify Taff Management or Brasher under the Policy. See, e.g., Trailer Bridge, Inc. v. Illinois Nat'l Ins. Co., 657 F.3d 1135, 1139, 1146 (11th Cir. 2011).

Having concluded the claims asserted in the underlying action are not covered under the plain terms of the Policy, the Court addresses Taff Management's other unavailing arguments: (1) that summary final judgment is not allowed because Taff Management's affirmative defenses were not addressed by Northfield in its Motion; and (2) Northfield is collaterally estopped from obtaining summary judgment on its declaratory judgment claims because Taff Management has relied on Northfield's defense for more than one year.

C. Affirmative defenses and summary judgment.

Taff Management contends that granting summary final judgment on Northfield's declaratory judgment claims would be error because Northfield's Motion did not address Taff Management's affirmative defenses, citing Stillman, supra. [ECF No. 67 at 2–3]. In Stillman, the Eleventh Circuit reversed the district court's final judgment because “[t]he summary judgment did not purport to adjudicate [the defendant's]․ other affirmative defenses” thereby rendering the final judgment “not final as to all the parties or as to any party or as to the whole subject matter of the litigation.” 88 F.3d at 913–14. Northfield counters: “Taff's reliance on its Affirmative Defenses, which either have been addressed or lack merit, does not preclude the entry of summary judgment in Northfield's favor.” [ECF No. 69 at 6].

While Taff Management is correct that, under Stillman, final judgment would not be appropriate if the resolution of Northfield's Motion did not resolve all claims and affirmative defenses asserted in this action, Taff Management never responded to Northfield's Amended Complaint so there are no affirmative defenses for this Court to consider. See Fed. R. Civ. P. 8(c); See Trasco Wellness, LLC v. Tampa Bay Spine & Sports Med., LLC, 806 F. Supp. 3d 1288, 1298 (M.D. Fla. 2025) (finding defendant abandoned affirmative defenses by failing to assert them in response to amended complaint). Yet, even if the Court considered Taff Management's answer and affirmative defenses asserted in response to the original complaint [ECF No. 22], only one of those defenses is actually an affirmative defense, and it can be resolved by way of this Order.

“An affirmative defense is one that admits to the complaint, but avoids liability, wholly or partly, by new allegations of excuse, justification or other negating matter.” Royal Palm Sav. Ass'n v. Pine Trace Corp., 716 F. Supp. 1416, 1420 (M.D. Fla. 1989) (citing Fla. East Coast Ry. Co. v. Peters, 72 Fla. 311, 73 So. 151 (1916)). A defense which simply points out a defect or lack of evidence in a plaintiff's case is not an affirmative defense. See In re Rawson Food Service, Inc., 846 F.2d 1343, 1349 (11th Cir. 1988). Furthermore, a court must not tolerate shotgun pleading of affirmative defenses and should not countenance vague and ambiguous defenses which do not respond to any particular count, allegation, or legal basis of a complaint. See Byrne v. Nezhat, 261 F.3d 1075, 1129 (11th Cir. 2001); Anderson v. Dist. Bd. of Trs. of Cent. Fla. Comm. Coll., 77 F.3d 364, 366–67 (11th Cir. 1996).

In its answer to the original complaint, Taff Management asserted the following eight “affirmative defenses” to Northfield's declaratory judgment claims: (1) failure to state a cause of action for declaratory relief; (2) the Policy is unambiguous such that no declaration is required by the court; (3) Northfield conflates the “auto” endorsement with the state-court allegations; (4) there is no actual controversy; (5) lack of ripeness; (6) court's discretion to decline to issue a declaratory judgment; (7) retaliatory filing of this case by Northfield (bad faith action); and (8) entitlement to attorney's fees. [Ans., ECF No. 22 at 5–9]. Upon review, only Affirmative Defense No. 5 (ripeness) qualifies as an affirmative defense, as explained below.

1. Affirmative Defense No. 1 “failure to state a claim”

Affirmative Defense No. 1 asserts “Plaintiff fails to state a cause of action for declaratory relief.” [ECF No. 22 at 5]. Specifically, the defense maintains “Plaintiff only alleges the first two elements [of such a claim] and fails to allege” the remaining three elements. [Id. at 6]. “Failure to state a claim” is an improper affirmative defense, and, as such, it is inappropriately asserted by Taff Management as an affirmative defense in this case. See Spiegel & Utrera, P.A. v. Stevens & Lee, P.C., No. 10-23451-CIV, 2011 WL 13223501, at *1 (S.D. Fla. Apr. 21, 2011) (King, J.); Lopez v. Leg.A.Sea Distr. Servs., LLC, No. 10-21847, 2010 WL 3767171, at *2 (S.D. Fla. Sept. 24, 2010) (King, J.) (noting “failure to state a claim” is improper basis for affirmative defense). The alleged insufficient pleading of the elements of Northfield's declaratory judgment claims constitutes a general denial, not an affirmative defense. See McLendon v. Carnival Corp., No. 20-cv-24939-BLOOM/Otazo-Reyes, 2021 WL 848945, at *3 (S.D. Fla. Mar. 5, 2021) (citing Flav-O-Rich, Inc. v. Rawson Food Serv., Inc., 846 F.2d 1343, 1349 (11th Cir. 1988) (“A defense that simply points out a defect or lack of evidence in the plaintiff's case is not an affirmative defense.”)). Accordingly, Affirmative Defense No. 1 is not an affirmative defense.

2. Affirmative Defense No. 2 “unambiguous” policy language

Affirmative Defendants No. 2 asserts: “Northfield erroneously claims that the auto exclusion of the policy limits or bars coverage in the State court action. However, Northfield grossly misinterprets the subject auto exclusion.” [ECF No. 22 at 6]. Whether Northfield has properly construed the Policy language neither admits the allegations of the Complaint nor responds to Northfield's claim for declaratory judgment “by new allegations of excuse, justification or other negating matter.” Royal Palm Sav. Ass'n, 716 F. Supp. at 1420. Accordingly, Affirmative Defense No. 2 is not an affirmative defense.

3. Affirmative Defense No. 3 “conflation” of the “auto” endorsement with the state-court allegations

Affirmative Defense No. 3 challenges the factual basis upon which Northfield invokes the “auto” endorsement. [ECF No. 22 at 7]. This defense alleges Brasher was not acting within the scope of his employment at the time of the fatal accident because he was on his way to work, had not yet punched the timeclock, and had not been instructed by Taff Management to move his car as alleged in the state-court complaint. [Id.]. This defense fails on two fronts. First, the defense is a general denial as it merely points out an alleged defect in Northfield's case. Second and more importantly, for purposes of Northfield's declaratory judgment claims, it does not matter whether Brasher was acting within the scope of his employment at the time of the fatal accident. As already stated above, if the trial court finds Brasher was acting within the scope of his employment, the claims are excluded from coverage under the “auto” endorsement. If the trial court finds Brasher was not acting within the scope of his employment, then Brasher would not be an “insured” under the Policy. Accordingly, summary final judgment of no coverage under either scenario does not run contrary to Stillman.

4. Affirmative Defense No. 4 “no actual controversy”

Affirmative Defense No. 4 states only: “Based on affirmative defenses 2 and 3 above, there is not a bona fide dispute between the parties with adverse legal interests that is of immediacy and existence to warrant a declaratory judgment.” [ECF No. 22 at 8]. This defense is deficient as it generally denies Northfield can meet the “actual controversy” requirement for asserting a claim under the Declaratory Judgment Act. Thus, it is a general denial and not an affirmative defense. In re Rawson Food Service, 846 F.2d at 1349.

5. Affirmative Defense No. 5 “lack of ripeness”

Affirmative Defense No. 5 states: “Based on affirmative defenses 2 and 3 above, this case is not yet ripe for adjudication because the dispute, if any, has not developed to a point where it can be properly decided by this Court.” [ECF No. 22 at 8]. “[R]ipeness is an appropriate ground for an affirmative defense.” Penn-Am. Ins. Co. v. Pavillion Foods, Inc., No. 18-62656-CIV, 2019 WL 2105880, at *2 (S.D. Fla. Mar. 20, 2019) (citing Advocate Commc'ns, Inc. v. Town Found., Inc., No. 04-61408-CIV, 2005 WL 8155323, at *2 (S.D. Fla. Aug. 10, 2005)). That said, Taff Management has made no showing as to why Northfield's declaratory judgment claims are not ripe—beyond its preference that this Court wait to resolve Northfield's claims until after the state court resolves Taff Management's motion for summary judgment. That is not part of a ripeness inquiry. A ripeness inquiry consists of two determinations: (a) the hardship to the parties of withholding court consideration; and (b) the fitness of the issues for judicial decision. Nat'l Park Hosp. Ass'n v. Dep't of Interior, 538 U.S. 803, 808, 123 S.Ct. 2026, 155 L.Ed.2d 1017 (2003). Supreme Court decisions implicitly require both elements to classify a case as “ripe” for judicial decision-making. Compare Poe v. Ullman, 367 U.S. 497, 81 S.Ct. 1752, 6 L.Ed.2d 989 (1961) (denying that the case was ripe despite an extensive factual background with no future contingencies affecting justiciability), with Socialist Labor Party v. Gilligan, 406 U.S. 583, 588, 92 S.Ct. 1716, 32 L.Ed.2d 317 (1972) (acknowledging hardship but finding the case unripe for want of an adequate record).

The Declaratory Judgment Act grants to the federal district courts the power to “declare the rights and other legal relations of any interested party seeking such declaration, whether or not further relief is or could be sought.” 28 U.S.C. § 2201. An essential element for every declaratory judgment action is the existence of an “actual controversy” between the parties. Aetna Life Ins. Co. of Hartford, Conn. v. Haworth, 300 U.S. 227, 239–40, 57 S.Ct. 461, 81 L.Ed. 617 (1937). An actual controversy exists when “there is a substantial controversy, between parties having adverse legal interests, of sufficient immediacy and reality to warrant the issuance of a declaratory judgment.” Md. Cas. Co. v. Pac. Coal & Oil Co., 312 U.S. 270, 273, 61 S.Ct. 510, 85 L.Ed. 826 (1941). Ordinarily, a controversy is not sufficiently immediate or real where the parties’ dispute is only hypothetical and not yet ripe, has been rendered moot, or where the court's resolution of the matter would be purely academic. See Texas v. United States, 523 U.S. 296, 300–01, 118 S.Ct. 1257, 140 L.Ed.2d 406 (1998); Aetna Life Ins. Co., 300 U.S. at 240–41, 57 S.Ct. 461. On the other hand, a court should permit a claim for declaratory judgment to proceed where declaratory relief would (1) “serve a useful purpose in clarifying and settling the legal relations in issue,” and (2) “terminate and afford relief from the uncertainty, insecurity, and controversy giving rise to the proceeding.” Volvo Constr. Equip. N. Am., Inc. v. CLM Equip. Co., 386 F.3d 581, 594 (4th Cir. 2004); accord Allstate Ins. Co. v. Emp'rs Liab. Assurance Corp., 445 F.2d 1278, 1280 (5th Cir. 1971).

“[I]n the context of an insurance-coverage dispute, when the facts and circumstances indicate that a claim is likely to be brought, the claim has sufficiently ripened to warrant declaratory judgment.” Nat'l Gen. Ins. Online, Inc. v. Black, No. 5:15-cv-111-Oc-30PRL, 2015 WL 5009703, at *3 (M.D. Fla. Aug. 24, 2015) (emphasis in original). Here, the claims have been brought and are now being litigated in state court. Thus, a declaratory judgment will serve the useful purpose in settling the parties’ legal obligations and will afford relief from the uncertainty, insecurity, and controversy giving rise to the proceedings. See Mt. Hawley Ins. Co. v. Tactic Sec. Enf't, Inc., 252 F. Supp. 3d 1307, 1310 (M.D. Fla. 2017) (citing Mid–Continental Cas. Co. v. Devonshire Props., Inc., No. 8:15-cv-1049-T-17JSS, 2015 WL 12831311, at *2 (M.D. Fla. Nov. 12, 2015)) (finding insurance coverage dispute sufficiently ripe where declaration would settle the parties’ legal obligations and “help to facilitate an early resolution of the parties’ coverage issues”).

Accordingly, Northfield's claims asserted under the Declaratory Judgment Act are ripe for resolution.

6. Affirmative Defense No. 6 “court's discretion”

Affirmative Defense No. 6 states: “[T]his action is inappropriate because Northfield is seeking declaratory judgment based upon an illusory controversy, to wit: the auto exclusion Northfield relies upon to justify this action, by its plain terms, does not even apply to the facts of the underlying State court case.” [ECF No. 22 at 8]. Once again, Defendants’ taking issue with the merits of Northfield's claims is not an affirmative defense. In re Rawson Food Service, 846 F.2d at 1349.

7. Affirmative Defense No. 7 “retaliatory filing”

Affirmative Defense No. 7 alleges: “On July 25, 2025, Northfield offered TAFF a renewal of its insurance policy with a substantial increase in premiums, which TAFF rejected. Notably, less than a week later on August 1, 2025 (and after defending TAFF for many months), Northfield filed this action against TAFF in retaliation for its non-renewal of its insurance policy with an increase in premiums, which would have offset Northfield's indemnification in the State court case.” [ECF No. 22 at 9]. Affirmative Defense No. 7, therefore, improperly attempts to assert a bad faith claim against Northfield in the form of an affirmative defense. However, “ ‘bad faith’ actions do not arise by way of an affirmative defense․ They arise as a separate and divisible action once a court has determined the issue of coverage in favor of the insured or the injured third-party.” Cont'l Cas. Co. v. City of Jacksonville, 550 F. Supp. 2d 1312, 1336 (M.D. Fla. 2007), aff'd, 283 F. App'x 686 (11th Cir. 2008) (citing Blanchard v. State Farm Mut. Auto. Ins. Co., 575 So. 2d 1289, 1291 (Fla. 1991)). The Court notes that Taff Management did not assert a bad faith counterclaim in this action. [See ECF No. 22]. Thus, Taff Management cannot assert a bad faith claim against Northfield as an affirmative defense, especially where, as here, there is no coverage under the Policy.

8. Affirmative Defense No. 8 “entitlement to attorney's fees”

Affirmative Defense No. 8 is one sentence that reads: “TAFF is entitled to the recovery of its attorney's fees herein pursuant to Fla. Stat. §§ 627.428, 624.155, and the Northfield insurance policy vis-à-vis Fla. Stat. § 57.105 (7).” [ECF No. 22 at 9]. This affirmative defense

is inadequate because it merely states an entitlement to attorneys’ fees and then references several statutes without any explanation as to how fees are appropriate. The ․ defense is also only one sentence long and fails to describe how any of the statutes apply to an entitlement of attorneys’ fees. This means that the defense lacks the necessary factual support to comply with Rule 8, and fails to explain or give notice to Plaintiff as to how it applies to the facts of this case. This alone renders the ․ affirmative defense defective as a matter of law. See Perlman v. Wells Fargo Bank, N.A., 2014 WL 4449602, at *2 (S.D. Fla. Sept. 10, 2014) (striking affirmative defense that “state legal doctrines or terms, but neither state how or why such defenses might apply to Plaintiff's claims, nor state facts in support of their application.”).

Tokio Marine Specialty Ins. Co. v. Ramos, No. 19-22069-CIV, 2019 WL 4573258, at *4 (S.D. Fla. Sept. 20, 2019) (granting motion to strike affirmative defense seeking attorney's fees without meeting Rule 8’s pleading requirements). Accordingly, Affirmative Defense No. 8 is not a viable defense.

In sum, none of Taff Management's “affirmative defenses” forecloses the entry of summary final judgment in Northfield's favor.

Finally, the Court rejects Taff Management's contention that Northfield's assumption of the defense of the underlying litigation (under a reservation of rights) estops it from obtaining summary judgment until after the state court resolves Taff Management's own motion for summary judgment.

D. Equitable estoppel and the undertaking of a defense.

As a last-ditch effort, Taff Management looks to equitable principles to avoid summary judgment. Taff Management contends Northfield is equitably estopped from withdrawing from the underlying representation because Taff Management has relied on Northfield's assumption of the undertaking “for well over a year.” [ECF No. 67 at 4]. Taff Management, however, cites no case holding that an insurer is estopped from obtaining a “no coverage” declaration from a federal court because the insurer has defended a state-court tort action against an insured for a certain period of time. [See id.]. Furthermore, Taff Management never asserted waiver and estoppel as an affirmative defense in this action. [See Ans., ECF No. 22 at 5–9].

In response, Northfield cites Scottsdale Ins. Co. v. Outrigger Beach Club Condo. Ass'n, 304 F. Supp. 3d 1208, 1214 (M.D. Fla. 2018) (citing Doe v. Allstate Ins. Co., 653 So. 2d 371, 373 (Fla. 1995)) for the “well-established” principle that “an insurer's coverage or restrictions on the coverage cannot be extended by the doctrine of waiver and estoppel.” In Scottsdale Ins. Co., the district court noted “[a]n exception to the rule [which] provides that when an insurance company assumes the defense of an action, with knowledge, actual or presumed, of facts which would have permitted it to deny coverage, it may be estopped from subsequently raising the defense of non-coverage.” 304 F. Supp. 3d at 1214. (quoting Cigarette Racing Team, Inc. v. Parliament Ins. Co., 395 So. 2d 1238, 1239–1240 (Fla. Dist. Ct. App. 1981)) (internal quotations omitted). The court further explained that estoppel theories typically arise in situations where an insurer fails to issue reservation of rights letters to the insured, noting that “[r]eservation of rights letters diminish the likelihood that insureds will experience a ‘false sense of security’ or fail to investigate a potential lack of coverage on its own.” Id. (citing Hannover Ins. Co. v. Dolly Trans Freight, Inc., No. 6:05–cv–576–Orl–19DAB, 2006 WL 1169496, at *7 (M.D. Fla. May 2, 2006)). Consequently, the doctrine of waiver and estoppel “applies when the insured proves prejudice and the insurer fails to issue a reservation of rights letter to the insured.” Id. (first citing Doe, 653 So. 2d at 372, then citing Coregis Ins. Co. v. McCollum, 961 F. Supp. 1572, 1578 (M.D. Fla. 1997) (emphasis in original)).

Taff Management's invocation of equitable estoppel at this stage of the litigation comes too late and brings too little with it. First and foremost, equitable estoppel was not pleaded in Taff Management's initial Answer and no affirmative defenses whatsoever were pleaded in response to the Amended Complaint. Consequently, the claim is not properly before the Court. See Britt v. IEC Corp., No. 20-60814-CIV, 2021 WL 4147714, at *5 n.2 (S.D. Fla. Sept. 13, 2021) (rejecting plaintiffs’ assertion of promissory estoppel in their opposition brief where plaintiffs did not assert a promissory estoppel cause of action in their complaint); Burger King Corp. v. Lumbermens Mut. Cas. Co., 410 F. Supp. 2d 1249, 1259 (S.D. Fla. 2005) (rejecting party's argument premised on a theory of promissory estoppel because the party never raised it in its complaint or answer and explaining “a court cannot create coverage by equitable estoppel”) (citations omitted).

And, even if Taff Management had asserted equitable estoppel as an affirmative defense, Florida law is clear that the doctrine cannot be used to expand coverage under the Policy. See 6 L's Packing Co. v. Fla. Farm Bureau Mut. Ins. Co., 268 So. 2d 560, 563–64 (Fla. Dist. Ct. App. 1972) (finding that under Florida law, “the insurer's [c]overage or restrictions on the [c]overage [as stated in the policy] cannot be extended by the doctrine of waiver and estoppel”); U.S. Fire Ins. Co. v. Morejon, 338 So. 2d 223, 225 (Fla. Dist. Ct. App. 1976) (“[A] court should not rewrite a contract of insurance extending the coverage afforded beyond that plainly set forth in the insurance contract.”) (citations omitted).

This Court has concluded there is no coverage under the Policy for the claims asserted in the underlying state-court action. The Court will not rewrite the Policy to require Northfield to continue to defend claims excluded by the parties’ insurance contract under an equitable theory. Additionally, Taff Management's dependence upon a heretofore free defense for more than one year does not establish prejudice. Prejudice requires a detrimental change in position. See United Contractors, Inc. v. United Construction Corp., 187 So. 2d 695, 701–02 (Fla. Dist. Ct. App. 1966). Taff Management could not have a change in position where Northfield provided a defense under a reservation of rights letter, which Taff Management does not dispute. Accordingly, Taff Management cannot survive summary judgment on Northfield's declaratory judgement claims under a theory of equitable estoppel.

V. CONCLUSION

For all of the foregoing reasons, it is hereby ORDERED AND ADJUDGED as follows:

1. Plaintiff Northfield Insurance Company's Motion for Summary Judgment [ECF No. 63] is GRANTED.

2. The Clerk is directed to enter a declaratory judgment in favor of Plaintiff Northfield Insurance Company, and against Defendants Taff Management Corporation and David Brasher, reflecting that Plaintiff owes no duty to furnish a defense or to indemnify them under Policy No. WS553866 in Failla v. Brasher and Taff Mgmt., Case No. CACE-25-002641 (03) (11th Jud. Cir., Broward Cnty., Fla.).

3. The Clerk is DIRECTED to CLOSE this case.

4. All deadlines are TERMINATED and any other pending motions are DENIED AS MOOT.

DONE AND ORDERED in the Southern District of Florida on July 6, 2026.

DAVID S. LEIBOWITZ UNITED STATES DISTRICT JUDGE