With ever more frequency, insurers have started to raise affirmative defenses in extra-contractual cases focusing on the insured/claimant’s mindset during the settlement process. Generally, these defenses argue the insured/claimant “set-up” the insurer for bad faith and/or had no intention of settling the underlying insurance claim. These are generally followed by overbroad requests for the file of the insured/claimant’s attorney as well as requests to depose the attorney that handled the underlying claim.
These types of requests risk infringing on materials protected by the attorney-client privilege and work-product doctrine. Those privileges belong to the insured/claimant and can only be waived affirmatively or through implication by the insured/claimant. An opposing party’s actions or defenses are meaningless when evaluating whether privileges have been waived as Progressive recently learned.
Kesler v. Progressive Select Ins. Co., 2026 WL 885992 (Fla. Ct. App. Apr. 1, 2026)
Bridgette Kesler was injured in a wreck with an individual driving a stolen vehicle. Unsurprisingly, the other driver did not have insurance coverage and Bridgette was left with an uninsured motorist claim against Progressive, her insurer. The parties apparently agreed that Kesler’s policy with Progressive provided $200,000 in uninsured motorist coverage.
Claims Made to Progressive
Progressive was quickly notified of the loss. In addition, Kesler retained Amy Catledge at the Ruth Law Firm to represent her for claims arising out of the wreck with the drunk driver. Five months after the wreck, Catledge sent a demand to Progressive for the UM limits. Included in the demand were Kesler’s medical records and bills. Instead of paying the UM limits, Progressive offered $43,000 to settle Kesler’s claims. Kesler rejected that offer and filed a lawsuit seeking to recover the UM benefits.
Early Stages of UM Lawsuit
Initially, Kesler’s lawsuit against Progressive only involved a claim to recover the UM benefits. During this initial period, Kesler followed a Florida statutory procedure to give Progressive another opportunity to pay her the UM limits. Progressive chose not to do so during the statutory time period permitted by Florida law.
Kesler then moved to amend her lawsuit to include a claim for bad faith against Progressive. The Court allowed Kesler to amend but stayed the bad faith claim until the resolution of her claim for UM benefits.
Kesler’s UM claim proceeded to a jury trial and the jury determined Kesler was entitled to UM benefits and had sustained roughly $1.7 million in damages. The trial court entered a judgment finding Progressive liable for $200,000 in UM benefits. Additionally, the court authorized Kesler’s bad faith claim against Progressive to go forward.
Bad Faith Claim and Discovery Dispute
During the Bad Faith litigation, Progressive sought to depose Catledge. At the deposition, Progressive asked Catledge several questions regarding “whether and Kesler was willing to negotiate for or accept less than policy limits.” Catledge refused to answer on attorney-client privilege grounds. Progressive also asked Catledge whether “she always demands policy limits,” how she calculates intangible damages and questions regarding how Catledge’s law firm communicates settlement offers between employees of the law firm. Catledge refused to answer these questions on work-product grounds.
Progressive filed a motion to compel Catledge to answer the above questions. Progressive argued the questions were relevant to Kesler’s motives for filing the bad faith claim and whether Progressive had acted in bad faith by failing to settle when Kesler had no intention of settling. Progressive further argued any attorney-client privilege had been waived as a result of Kesler filing the bad faith claim. Progressive also took the position that work product protections for information generated in an underlying claim could not apply in a bad faith case. Progressive also argued it had a substantial need for the information so it could present its defense that Kesler never intended to settle her UM claim.
The trial court granted Progressive’s motion to compel and ordered that Catledge sit for a second deposition and provide answers to Progressive’s questions. The trial court did not provide any factual or legal analysis for its decision or explain why it was overruling the attorney-client and work product privileges.
Appellate Decision
Kesler immediately challenged the trial court’s court order requiring a second deposition of Catledge and again argued the order would require the disclosure of information protected by attorney-client and work product privileges. Progressive countered that even if Catledge’s information was protected by attorney-client privilege, it was relevant and discoverable and reiterated that it believed the privilege had been waived by the filing of the bad faith claim. Progressive also reiterated its arguments concerning the inapplicability of the work-product protection after the filing of a bad faith claim.
The appellate court took issue with Progressive’s positions and ruled in favor of Kesler. Concerning applicability of the attorney-client privilege, the Court outright rejected Progressive’s claims that because Kesler’s willingness to settle for the policy was relevant, it was discoverable regardless of whether it was privileged. Additionally, the court determined that Kesler had not waived any privilege by filing the bad faith claim or put conversations with her attorneys at issue. Instead, Progressive raised the issue of Kesler’s unwillingness to settle as an affirmative defense. Only Kesler could waive privileges and Progressive pursuing an affirmative defense could not waive Kesler’s privileges.
The court also rejected Progressive’s attempts to defeat the work-product objections. First, the court declared outright that Progressive’s assertion that the work product protections could not be applied in a bad faith claim as to information generated during the underlying insurance claim. Further, the court noted that Progressive had failed to make a sufficient showing that it had a substantial need for the information it sought to obtain from Catledge.
Kesler shouldn’t come as a surprise as Progressive’s position on the inapplicability of privileges in bad faith cases was extreme. The fundamental protections afforded by the work-product doctrine and attorney-client privilege cannot change depending on the nature of the claims being brought. Just because the information might be helpful to the insurer’s defenses does not make it discoverable and the assertion of a certain defense cannot waive the insured’s or claimant’s valid claim of privilege.
While not directly discussed in Kesler, Progressive’s insistence on breaching attorney-client privilege and work product protections to discover Kesler’s “willingness to settle” was unnecessary and nearly laughable. Kesler and her attorney had submitted a policy limits demand to Progressive. Common sense would indicate that she was willing to settle, just not at Progressive’s misguided and undervalued offers.
Need Assistance with a Bad Faith Situation?
Kirk Presley enjoys helping individuals and other lawyers with bad faith cases. If you would like to speak with him about a bad faith case email him at kirk@presleyandpresley.com or call him at (816) 931-4611.