Why Michelle Obama Disliked Working at Sidley—and the Lessons That Still Apply

Her buffed walnut desk. Her view from the 47th floor overlooking Lake Michigan. Recruiting law students. The money.

I’ve been reading Obama’s autobiography “Becoming,” and have been struck by her dismal depiction of the three years she spent as an associate at the firm from 1988 to 1991.

The National Association for Law Placement puts out a periodic report it calls “Keeping the Keepers” about associate retention. Sidley for a brief time employed two of the keeping-est keepers you could imagine: Michelle Robinson and Barack Obama, who met in 1989 when he was a summer associate at the firm.

In hindsight, it seems clear that no matter how nice, how appreciative, how flattering Sidley leaders were to Barack (and according to Michelle, they were very), the 44th president was never going to pursue a career in Big Law. That was not his path.

But the future first lady? The way she tells it in her autobiography, practicing law simply wasn’t for her.

“I hated being a lawyer. I wasn’t suited to the work. I felt empty doing it, even if I was plenty good at it,” Obama wrote.

When the Obamas were based in Illinois, they quickly jumped ship from private law firms (where one is expected to work and produce earnings for the law office) to the public sector where “no show” six figure jobs exist for the politically anointed. During most of their “careers,” Michelle was the primary earner in their household. Her salaries were greater than her husband’s primarily because his work as a state legislator and an adjunct law professor were part-time positions. Barack even rejected an offer to teach law as a full-time faculty member at the University of Chicago. He was not interested in real employment, he wanted to manufacture a fake resume’ for politics.

Michelle’s important position with the City of Chicago allowed her time to complete crossword puzzles and read romance novels while at City Hall (Jesse Jackson was her sponsor who helped secure her job under Mayor Richard M. Daley). No one knows what she did at the University of Chicago Hospital. The hospital eliminated her position as soon as she moved to the White House.

Sidley must not have gotten the memo that she was diversity window dressing for the clients who care about such things (as opposed to clients who want the best lawyers available doing their work). “What do you mean you want me to bill a minimum of 2,000 hours a year at a 95% realization rate?!? I’m here to aid your optics, not to actually WORK!”

The story of her entire adult life.

Actually, we do have an idea what she did at the University of Chicago Medical Center (It isn't so far in the past that archeology was required!) from this Washington Post article from August 22, 2008: Obama Camp Has Many Ties to Wife's Employer

Here is an excerpt of the hagiographic article:

"...A few years ago, executives at the prestigious University of Chicago Medical Center were concerned that an increasing number of patients were arriving at their emergency room with what the executives considered to be non-urgent complaints. The visits were costly to the hospital, and many of the patients, coming from the surrounding South Side neighborhood, were poor and uninsured.

Michelle Obama, an executive at the medical center, launched an innovative program to steer the patients to existing neighborhood clinics to deal with their health needs. (In the medical community, this is called "patient dumping". But when someone with the last name of "Obama" does it, it is called an "innovative program"...)

That effort, in time, inspired a broader program the hospital now calls its Urban Health Initiative. To ensure community support, Michelle Obama and others in late 2006 recommended that the hospital hire the firm of David Axelrod, who a few months later became the chief strategist for Barack Obama's presidential campaign.

Axelrod's firm recommended an aggressive promotional effort modeled on a political campaign -- appoint a campaign manager, conduct focus groups, target messages to specific constituencies, then recruit religious leaders and other third-party "validators." They, in turn, would write and submit opinion pieces to Chicago publications.

One key recommendation from Axelrod's firm: "Respond quickly to opposition activity..."

You get the idea.

Bingo. Most big law firms expect their associates and partners to produce. Zero and his wife were world-class grifters, anxious to get as much as they could for minimal effort. Had they remained at the firm, Mr. and Mrs. Obama would have been told (eventually) to shape up or ship out, unless they wanted to retain them as affirmative action window dressing. But even that was more work than they wanted.

And, unfortunately for all of us, they hit the jackpot.

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