U.S. Bankruptcy Judge John K. Olson will hang up his robe on Feb. 9, 2020, after a 14-year term on the Southern District of Florida bench in Fort Lauderdale.

Admitted to the bar in 1975, Olson practiced at Stearns Weaver Miller's Tampa office for 18 years before rising to his post in February 2006.

Olson did not respond to a request for comment about his retirement, but had sought reappointment from the U.S. Court of Appeals for the Eleventh Circuit in July. But he appears to have changed direction, because the appellate court has said it's seeking applicants until Dec. 2 to fill the vacancy.

Olson has acquired a reputation for brilliance and wit among both his advocates and critics — some of whom have raised questions about his temperament, and pointed to 10 occasions in which he's jailed lawyers and litigants.

Discrimination

Olson, who is in a same-sex marriage, has been the subject of whispered courthouse gossip for years—some of which malign his sexual orientation and his work for LGBTQ rights.

In a 2013 amicus brief to the U.S. Supreme Court, Olson wrote in support of Edith Windsor, whose legal fight for federal benefits for same-sex couples resulted in a landmark ruling.

The judge's brief detailed how he received a letter from the Administrative Office of the United States Courts terminating his enrollment in the Judicial Survivors' Annuities System because of his same-sex marriage. The benefits system was set up to provide financial security for the family of deceased federal judges, but it denied his husband that benefit.

But other rumors—and judicial misconduct complaints—have stemmed from allegations the judge has favored his spouse's employer, when that law firm has appeared before him in court.

Olson is married to bankruptcy attorney George Steven Fender, who has a solo practice in Fort Lauderdale. Their union has been the catalyst of multiple complaints from attorneys who sought Olson's removal from cases over alleged preferential treatment of Fender's former employer, Ruden McClosky Smith Schuster & Russell.

In one of those cases, a federal judge nullified a final judgment from Olson in favor of a bankruptcy trustee whose lawyers had hired Fender—then Olson's fiancée—while the litigation was pending.

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'Knowledge, fantastic wit'

U.S. Bankruptcy Judge Erik Kimball said he'll miss his colleague, who he said had "an encyclopedic knowledge of commercial and bankruptcy law" even before becoming a judge.

"Equally important for success as a professional and on the bench, he is one of those people who can quickly digest a mountain of detail and grasp the true kernel of a matter," Kimball said. "He also has an amazingly broad knowledge of history and culture, and employs that knowledge with fantastic wit."

U.S. Bankruptcy Judge Paul Hyman said he'll also miss Olson around the courthouse, calling him "a great colleague and friend."

Bankruptcy attorney Jacqueline Calderin said practicing before Olson is a privilege—which is sometimes even fun, thanks to his wit and engagement.

"He always took the bench well-prepared and brought with him a knowledge base that exceeded the bounds of the briefs before him. Even if I was on the losing side of a case, I knew that my argument and my client had received the utmost measure of attention, fairness and justice," Calderin said. "Our bar and our clients have suffered a material loss with his departure from the bench and I will miss him."

Olson's retirement, in Calderin's view, is like an athlete stopping at the top of his game, as "he definitely has more game in him."

Olson holds a bachelor's degree in history from Harvard University, where he graduated magna cum laude, and a law degree from Boston College of Law. He's chaired the Florida Bar's Business Law Section of the Florida Bar and the American Bar Association's Abuse of the Bankruptcy Subcommittee of the Business Bankruptcy Committee. His next move was unclear at press time.

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