Plaintiff-Appellant Timothy Daileader was the independent director and manager of an affiliated group of companies (together, “Oaktree”) in distress. Defendants-Appellees Certain Underwriters at Lloyds London Syndicate 1861, along with the other Defendants- Appellees, provided Oaktree with directors and officers liability insurance. Daileader is now defending himself in litigation involving 2  No. 23-690 Oaktree and seeks coverage from Syndicate 1861 for his defense. Syndicate 1861 denied Daileader’s insurance claim. Daileader then sought a preliminary injunction to enforce Syndicate 1861’s duty to defend. The district court (Gardephe, J.) denied Daileader’s motion, and Daileader appealed. We hold that the district court did not abuse its discretion in doing so. We therefore AFFIRM the district court’s order.

BACKGROUND Daileader’s dispute began with Oaktree’s troubles. Oaktree’s three affiliated healthcare companies were owned by Daniel McCollum. Starting in 2015, the United States and several qui tam relators brought suit against McCollum and Oaktree, alleging that Oaktree had been fraudulently mismanaged. McCollum eventually admitted in a civil proceeding to violating the Anti-Kickback Statute, 42 U.S.C. § 1320a-7b. App’x 176, 208. He also entered a plea agreement in a criminal prosecution for conspiracy to pay illegal kickbacks and to defraud government healthcare programs. App’x 210. In January 2018, with litigation against Oaktree pending, Oaktree defaulted on multiple loans. Between July and December 2018, Oaktree’s lenders appointed Daileader as the independent director and/or manager of the various Oaktree entities. 1 Daileader assumed these roles through his employer, Drivetrain, LLC, which 1 In July 2018, Daileader was appointed as sole director and sole manager of Oaktree Medical Centre, PC and LabSource, LLC. In December 2018, he was appointed as co-manager with McCollum of Oaktree Medical Center, LLC. In June 2019, he became Oaktree Medical Center’s sole manager, when the lenders removed McCollum as a co-manager.

3  No. 23-690 places investment professionals as independent directors of financially distressed companies.

Oaktree’s distress soon put Daileader at risk of personal liability. In September 2019, each of the Oaktree entities filed for Chapter 7 bankruptcy. In April 2021, the Chapter 7 Trustee sent a demand letter to Daileader alleging, among other things, that Daileader had breached his fiduciary duties to Oaktree by failing to file for Chapter 11 restructuring. The demand letter alleged damages ranging from $38 million to $925 million. In September 2021, the Trustee initiated adversary proceedings against Daileader and others in the U.S. Bankruptcy Court for the District of South Carolina, where Oaktree’s Chapter 7 bankruptcy case was pending. 2 Oaktree had purchased insurance protecting its directors and officers against some litigation expenses. Non-party Landmark American Insurance Company sold Oaktree a $1 million primary directors and officers (“D&O”) policy. Defendants-Appellees each sold Oaktree a “follow form” excess policy adopting the primary policy’s terms. Syndicate 1861 provided a first layer of excess coverage up to $1 million; the other excess insurers cumulatively provided another $8 million in coverage. Each of these policies includes a “duty to defend.” This means, among other things, that the insurance covered certain litigation costs arising from suits against Oaktree’s directors and officers. The parties do not dispute that Daileader is among those insured by Oaktree’s D&O policies.

2The Trustee filed three substantively identical adversary complaints, one for e