“Every part of him was cool and wet moving swiftly through the water, nothing, nothing in his way.”

That's a quote from the yearbook page of ex-Willkie Farr & Gallagher co-chairman Gordon Caplan, who graduated from Trinity, an elite private school in Manhattan, in 1984. It turns out I know several of his classmates, who shared the yearbook.

I have reservations about mining high school yearbooks a la Brett Kavanaugh for insight into a man 35 years later. But this particular quote—a standalone sentence on his page that's attributed to “G.R.C”—Caplan's initials— is so striking in its imagery. His exact reference is unclear, but it suggests a slippery, stealthy person racing ahead without obstacles.

Not anymore.

Caplan's attorneys on Friday said he plans to plead guilty to conspiracy to commit mail fraud and honest services mail fraud—charges which carry a maximum of 20 years in prison—in connection with the college admissions scandal.

It's a spectacular downfall, from The American Lawyer's “Dealmaker of the Year” in 2018 to being fired last week by Willkie Farr and facing certain disbarment as an admitted felon.

Caplan is certainly not the first Big Law partner to find himself on the wrong side of the law, but this is not your average, stole-from-an-IOLTA-account, bad lawyer story.

It's headline news: A heady mix of celebrities—other defendants include actresses Lori Loughlin and Felicity Huffman—plus wealth and privilege, all laid bare to confirm our worst suspicions that elites are gaming the system. The story, as they say in the news business, has legs. It's not going away, and people won't quickly forget it. Moreover, Caplan has the misfortune of having been recorded delivering one of the most damning and widely quoted lines in the 204-page affidavit: “It's just, to be honest, I'm not worried about the moral issue here.”

Ouch.

So what will become of him now?

His attorney Joshua Levy at Ropes & Gray did not respond to a request for comment, but I think it's safe to assume Caplan will not be getting anything close to 20 years behind bars. It's even conceivable he won't get any time at all, maybe just supervised release, community service and a fine.

Because as much as we the nation are collectively disgusted and angry, Caplan has one of the more sympathetic criminal motives: He wanted to help his daughter get into a good college.

Yes, he demonstrated the ethical compass of shark (“Cool and wet, moving swiftly through the water”?), but still. Who doesn't want to help their kid?

By comparison, other ex-Big Law partners currently doing time share a far less laudable motive: Greed.

For example, former Akin Gump Strauss Hauer & Feld partner Jeffrey Wertkin is currently incarcerated at a minimum security prison camp in Talladega, Alabama, where he's slated for release on January 24, 2020, according to the Federal Bureau of Prisons.

Wertkin pleaded guilty in late 2017 to stealing sealed whistleblower complaints from the Justice Department before he left his job there to join Akin Gump. He then attempted to sell one of the complaints for $310,000 to an undercover FBI agent.

Gordon Caplan in the yearbook of Trinity School in New York, 1984.

Or take Evan Greebel, Martin Shkreli's former attorney and co-defendant. The former partner at Katten Muchin Rosenman and Kaye Scholer is doing time at FCI Otisville in New York (named one of America's 10 cushiest prisons by Forbes), where he's slated for release on Feb. 5, 2020. He was convicted of conspiracy to commit wire fraud and conspiracy to commit securities fraud, working with Shkreli on what prosecutors called an elaborate Ponzi scheme.

Keila Ravelo, a former partner at Hunton & Williams and Willkie Farr, admitted to cheating the firms and a former corporate client, Mastercard Inc., in a $7.8 million fraud involving dummy litigation support companies. She's at FPC Alderson in West Virginia (the same prison camp where Martha Stewart did her time), scheduled for release on May 23, 2023.

There's also Walter “Chet” Little, an ex-partner at Foley & Lardner and Bradley Arant Boult Cummings. He pleaded guilty in late 2017 to one count of conspiring to commit securities fraud, using confidential client information about mergers, earnings and other events to make stock trades. Little is doing his time at FCP Montgomery in Alabama (also on the cushy prison list), due to get out this year on December 13.

And then what happens? What do once high-flying ex-lawyers do with themselves after they've served their time?

There's no common answer.

Plaintiffs giant Melvyn Weiss, who pleaded guilty to one count of racketeering conspiracy, retired to Florida and did a lot of fishing. He died last year.

His former partner William Lerach, who also went to prison, is mounting a comeback of sorts. The Financial Times reported in September that Lerach and his company, Pension Forensics, “are acting as consultants to his lawyer wife, Michelle Ciccarelli Lerach, in a lawsuit against Blackstone and KKR in Kentucky state court over losses in one of the state's largest pension plans.” The FT reports that the suit “is already being blamed for private equity and hedge fund managers pulling their business from Kentucky.”

Likewise, former Greenburg Traurig lawyer/ lobbyist Jack Abramoff, who served 43 months in prison in connection with a bribery scandal, is back working as a political operative. EE news reported in February that Abramoff is now the honorary chairman of the Protect American Values political action committee and has been sending out fundraising emails attacking efforts to combat climate change.

Former DOJ official Robert Coughlin II, who was caught up in the Abramoff scandal for accepting meals and gifts in exchange for favors, was sentenced in 2008 to three years of supervised release. In 2016, he had his law license restored by the D.C. Bar.

But the most feel-good post-prison story is that of Dickie Scruggs, the legendary plaintiffs lawyer who made a fortune suing the tobacco and asbestos industries. In 2008, he pleaded guilty to attempting to bribe a judge and was sentenced to five years in prison.

Mississippi-based Oxford Magazine in 2017 ran a lengthy profile of Scruggs, where he spoke of his time behind bars.

Because of his wealth and the fact that he had a home in the Bahamas, he was considered a flight risk. No cushy minimum security prison for him—he did the first portion of his sentence with hardened criminals. “It was like a casting call of 'The Walking Dead,'” he told David Magee writing for Oxford.

Eventually he was transferred to a lower-security facility and landed one of the most coveted prison jobs—as a teacher, helping fellow inmates earn high school equivalency degrees.

The experience inspired in him a crusade to improve adult education. After Scruggs was released from prison in 2013, he founded a nonprofit dedicated to adult basic education called Second Chance Mississippi. It now has a formal relationship with Mississippi's community colleges system and focuses on education and job training for adults.

Magee described dining out with Scruggs, who is now 72, in Oxford. “[I]t feels at times like being at the table with Archie Manning or Robert Khayat, since most everybody knows him and showers him with adoring affection.”

Scruggs described himself as “happier today than I have ever been before.” And he quoted Rhett Butler (one of the books he had time to read in prison was “Gone with the Wind”): “Until you've lost your reputation, you never realize what a burden it was or what freedom really is.”

Whether Caplan will come out on the other side a changed man is unknown, but at least there's the hope of finding something better in the end.

Read more: 

Willkie Cuts Ties as Gordon Caplan Plans Guilty Plea in College Cheating Case

Willkie's Gordon Caplan Appears in Court to Face College Admissions Charges

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