Gabe MacConaill was working on a life-defining case. The 42-year-old junior partner at global law firm Sidley Austin had been put on the bankruptcy of a company called Mattress Firm. The process was complicated and multipronged, taking 41 subsidiaries down with it.

In the months leading up to the bankruptcy filing in October 2018, many people surrounding MacConaill noticed he was isolating himself. He closed his office door more often. His friends rarely saw him. He worried aloud to his wife, Joanna Litt, that he didn’t have enough debtor experience and would be sued for malpractice.

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