Nonetheless, the not-so-subtle pressure to land clients and keep generating millions in revenue was evident in the email from Mr. DiCarmine. Much of Mr. Altorelli’s revenue came from one client — Capmark Financial Group, the former commercial mortgage business owned by General Motors that was sold to a private equity group in 2006. In its numerous corporate maneuvers, including a trip through bankruptcy court, Capmark was a veritable Mount Vesuvius of legal fees. Thomas Fairfield, then its general counsel, was a close friend of Mr. Altorelli’s and had worked with him years earlier in the LeBoeuf firm’s Hartford office. Mr. Altorelli landed the coveted role of debtor’s counsel to Capmark during its bankruptcy, which kept numerous Dewey & LeBoeuf lawyers occupied for years.

But Mr. DiCarmine noted in the 2011 email that without Capmark, “Your revenue production would not be in the range it has been and there is no ‘insurance’ that it will be at those levels in the future.” He went on, “But, we believe you will continue to hustle business, and deliver it, and are prepared to offer you the $5 million guarantee (for three years.)”

Mr. Altorelli replied in an email: “It is not just money. I have bigger concerns with the firm, and a two-page piece of paper that says I should make x over the next 3 years if I bring in around 100 million sort of tells me that I am expected to keep the firm afloat.” He added, “I am pretty sure I will deliver as I have every single year of my career.”

Mr. Altorelli never signed the proffered multimillion-dollar contract. He did stay until nearly the end, and former partners credit him with valiant efforts to save the firm, including forgoing much of his compensation in 2012. He left for what he surely thought would be a comfortable future at DLA Piper.

He soon realized otherwise. Just days later, on April 8, 2012, The New York Post ran an article with the headline, “Anna: The Spy Who Loved Me,” disclosing their previous relationship. (The timing, nearly two years after Ms. Chapman was deported, suggests someone at Dewey leaked the story.) It couldn’t have come at a worse time, just as he was recruiting clients to his new firm. Whether it had any impact, his billings at DLA Piper haven’t nearly reached the levels they had been at Dewey & LeBoeuf. Although he still represents Capmark, all the deals listed on his profile at DLA Piper date from his time at Dewey & LeBoeuf.

Worse, from a financial perspective, Dewey & LeBoeuf’s bankruptcy trustee announced that he would seek to claw back partner compensation from the years 2011 and 2012. This was especially onerous for Mr. Altorelli. At the firm’s request, he had agreed to be paid the $2 million in compensation due him in 2010 early in 2011, which pushed it into the clawback period. The trustee offered to settle with Mr. Altorelli for about $1.4 million, but wouldn’t exempt the $2 million. Mr. Altorelli refused to settle. The trustee subsequently sued him for $12.9 million.

Then there’s the Internal Revenue Service. As part of the bankruptcy proceeding, many of the firm’s creditors waived or reduced their claims. All canceled debt is treated as income to the firm for tax purposes, even though no money changed hands. Because Mr. Altorelli earned so much from the firm, his share of this so-called phantom income was correspondingly high. The I.R.S. is seeking tax on $8.9 million of income in 2011 alone.