The story of the tangled relationship between Casey Greenfield, a rising star in New York legal circles, and Jeffrey Toobin, arguably the nation’s leading legal journalist, has gone mainstream. Over the long weekend, the New York Times wrote an 1,800-word story on their affair.

Actually, to be fair, the story was mainly about Casey Greenfield and her law partner, Scott Labby, launching their boutique law firm, Greenfield Labby (which has a beautifully designed website, by the way). The firm specializes in what the Times describes as “high-stakes family law,” which includes not just divorce and custody litigation, but “[c]risis management, strategic planning and contract resolution.”

The story of Greenfield and Labby launching a new small law firm is both interesting and inspiring. But, at the same time, it’s one that we’ve seen — and written — before. You can read our earlier write-up of Greenfield Labby’s launch over here.

The most interesting parts of the NYT piece concern Casey Greenfield’s affair with the then-married (and still-married) Jeff Toobin, a long-running relationship that produced a baby boy. The writer, Times reporter Robin Finn, unearthed several juicy, previously unreported details….

Finn’s article can be read in full here. I found it immensely enjoyable and elegantly written, but apparently not everyone shares my view — there are over 100 reader comments on the piece, and many of them are negative. Some of them go something like this: “Why is this in the pages of the New York Times? Why is this newsworthy? Don’t new law firms launch every week in New York City?”

Yes, they do. But how many new firms have this kind of backstory, and launch with this big a splash?

Empowerment is a major theme in Ms. Greenfield’s personal and professional lives, which have neatly dovetailed since she emerged from her own heavyweight and highly public bout of custody litigation — she shares an out-of-wedlock child with the married legal journalist Jeffrey Toobin — to form the boutique firm Greenfield Labby. On Wednesday, it will celebrate its [launch] with a party at the Modern, the Danny Meyer restaurant at the Museum of Modern Art. Nearly 200 people, many in the boldface category, have received invitations. It will not be a typical law firm fete.

(I’m planning to attend. Please come up and say hello if you see me there tomorrow night.)

The firm, which Ms. Greenfield formed with Scott Labby, 39, a Yale Law School classmate and a former boyfriend, has roughly two dozen well-heeled clients and employs five lawyers, in Manhattan and in Boston. It sees itself as an elite group of “country lawyers” for glittering urban professionals with lots to gain — or lose.

Considering that the firm launched just a few months ago, it’s impressive that Greenfield Labby already has this many clients and lawyers. In addition to the name partners, the firm has three other attorneys: of counsel Courtney Clark, a Yale Law School graduate who previously practiced at Goodwin Procter and Sherin and Lodgen; of counsel Kyle Pasewark, also a Yale Law grad, who joined the firm from Debevoise & Plimpton; and Shanna Giora-Gorfajn, a Columbia Law School graduate with extensive experience in family law.

Here’s another reason why the Greenfield Labby launch is newsworthy:

[Casey Greenfield is the] self-described “product of a modern splintered and re-glued family” — her father, the political pundit and television commentator Jeff Greenfield, is thrice-married, and after a privileged upbringing on the Upper West Side, Ms. Greenfield left for boarding school at Andover when her parents divorced. (Her mother, Carrie Carmichael, was Mr. Greenfield’s first wife.)

Yes, that’s right: another celebrity connection. Casey’s father, prominent political commentator Jeff Greenfield, is a familiar face to the well-read, well-heeled types who watch the Sunday shows and ride the Acela train between New York and D.C. They’re also the type of people who read articles in the New Yorker by Jeff Toobin (who is, awkwardly enough, a former CNN colleague of Jeff Greenfield).

Speaking of Toobin, let’s get into the nitty-gritty of the Greenfield/Toobin relationship. The Times reports:

[In 2008,] as a first-year associate at Gibson Dunn, a strait-laced corporate law firm, [Greenfield] found herself single and pregnant at 35.

The presumptive father was Mr. Toobin, a senior political analyst for CNN, staff writer for The New Yorker, best-selling author, married father of two teenagers and a close friend of Justice Elena Kagan of the Supreme Court, a classmate of his from Harvard Law. Ms. Greenfield met Mr. Toobin in the Condé Nast cafeteria when, while taking a breather from law school in her mid-20s, she worked as a fact-checker for Glamour magazine. They fell into a secretive off-and-on relationship spanning nearly a decade.

Reading this, my reaction was, “Wow, I didn’t know the affair lasted for almost ten years!” And I didn’t know that they met in the famous Condé Nast cafeteria — the basis for this hilarious scene in The Devil Wears Prada.

(I also didn’t know that Glamour employs fact-checkers. How do you verify the veracity of 5 Kinky Things Men Are Craving? I sincerely hope that Jeffrey Toobin was not involved in any such “fact-checking” by Casey Greenfield.)

When Ms. Greenfield first informed him of her pregnancy, she said, Mr. Toobin questioned the paternity, balked at submitting to a test and vowed to take no responsibility for a baby he wasn’t sure was his. Both hired lawyers. Inevitably, the tabloids and gossip sites took notice of the scandal, dropping increasingly detailed hints about the behind-the-scenes drama.

Considering how long the affair allegedly lasted, I think Toobin’s reaction to the pregnancy news becomes more understandable. If this truly was an on-again, off-again relationship that spanned almost a decade, a time during which Greenfield presumably had other paramours as well, it’s not unreasonable for Toobin to question whether the baby was actually his.

“The one time you really don’t want to get pregnant is when you’re single and the other person is married and you’re working as a first-year junior associate at a law firm in a hard-core phase of trying to prove yourself to them,” Ms. Greenfield recalled last week. She said she ruled out an abortion. She did not delude herself that the emotional nadir of her life would qualify for much external sympathy. “I had a job at a prestigious firm,” she said, “a law degree from Yale that was paid for, a wonderful support group of friends.” But when she informed her parents that she was pregnant, she did not say by whom.

In March 2009, Ms. Greenfield had a baby boy and named him Roderick Henry Greenfield: Roderick is Mr. Labby’s middle name, and Henry is her father’s actual first name. She went on maternity leave for four months and then returned to Gibson Dunn until January 2011. She also sued Mr. Toobin for child support and custody of the baby, while being officially represented by Heidi Harris of Aronson, Mayefsky & Sloan, a preeminent matrimonial firm, and unofficially assisted by Mr. Labby, whom she calls her “fixer.”

Speaking for myself, I did find Greenfield sympathetic at the time of these events. Being a pregnant single mother, while working at a demanding law firm like Gibson Dunn and litigating child support issues on the side, couldn’t have been easy. As one of Greenfield’s friends told ATL at the time, “Casey has been through a lot, and is kind of a superhero. She’s been a full-time single mom while working at Biglaw, all while fighting a rather ugly battle with [Toobin], and so the last 20 months or so have been pretty hard on her. Casey’s an amazing person and an amazing mom, and she deserves better.”

Where do things stand now in the Greenfield v. Toobin litigation? And what does Toobin have to say about these matters?


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