A Florida federal court ruled Thursday that a unit of American International Group Inc. does not have to cover a Jacksonville maritime company that reportedly spent over $2.5 million defending an executive from antitrust charges.

In Crowley Maritime Corp. vs. National Union Fire Insurance Co. of Pittsburgh, Pa., Judge Timothy Corrigan of the U.S. District Court for the Middle District of Florida ruled that Crowley was in a “Catch-22” situation in its attempt to receive payment.

National Union issued an executive and organization liability policy to Crowley in November 2007, according to court records. The policy provides that the “criminal . . . investigation of an insured person” triggers coverage once the “insured person is identified in writing” by an “investigating authority as a person against whom” a criminal proceeding has commenced.

On April 17, 2008, the U.S. Department of Justice served a search warrant at Crowley Liner Services, a Crowley subsidiary, seeking various documents from the company and four Crowley Liner employees, including Tom Farmer, a vice president of Crowley Liner. He was also issued a subpoena on April 17, 2008.

The affidavit listed Mr. Farmer as a “subject” of the investigation; the affidavit was sealed until 2015.

On April 25, 2008, Crowley provided National Union notice of a claim under the policy, sent copies of the search warrant and Mr. Farmer’s subpoena and told National Union that the affidavit was sealed. Crowley requested that National Union advance Mr. Farmer’s defense costs.

National Union maintained that “based on the documentation currently available,” the policy did not provide coverage for Mr. Farmer because it did not identify Mr. Farmer “in writing as a target of any investigation.”

During this time, the U.S. Justice Department investigation continued, and in February 2013 the government offered Mr. Farmer a plea deal, which identified him in writing as a target of an investigation. National Union agreed to cover Mr. Farmer’s subsequent defense costs because the plea deal materialized before the end of the discovery period.

Mr. Farmer did not accept the plea deal, and a jury acquitted him of price-fixing and bid-rigging charges related to a charge he conspired with competitors to fix prices in the U.S. mainland-Puerto Rico trade. Following the acquittal, Crowley obtained a copy of the unsealed affidavit and asked National Union to cover Mr. Farmer’s defense costs from the original notice of a potential claim in 2008 until February 2013 because in 2008 the affidavit identified him as the subject of an investigation.

Crowley began an arbitration action on March 7, 2012, to recover Farmer’s defense costs, the ruling said. The parties did not obtain the affidavit during the arbitration, and the arbitrators determined that everything Crowley had submitted to National Union through 2012 did not amount to a claim.

“The answer is a Catch- 22 for Crowley,” Judge Corrigan wrote in his decision. “If it was in 2008, then Crowley is precluded from re-litigating the issue; if it was in 2015, Crowley’s demand is barred by the plain text of the policy’s discovery period.”

The policy has a limited period in which claims can be reported, Judge Corrigan said, and claims reported outside of that period — regardless of the circumstances — are not covered. Although the affidavit existed in 2008, its content was unknown and unattainable until 2015, and it was at that time that Crowley demanded coverage based upon the affidavit.

But at that time, the decision said, the discovery period had expired, so Crowley’s reporting of the claim was untimely. If, contrary to the court’s decision, the claim based on the affidavit is deemed reported in 2008, Crowley is precluded from bringing this action because of the intervening arbitration decision.

“Either way, Judge Corrigan wrote, “Crowley cannot recover.”

A Crowley representative had no comment.