Kagan joined the staff there in 1991 and won tenure in 1995. Obama was a part-time lecturer there between 1992 and 2004, when he was elected to the U.S. Senate, but according to reports she tried to convice him to pursue a tenure track.
Obviously Obama had more grandiose ideas about where his career would lead him, but what a perfect bookend now that he's poised to nominate her to become the next Supreme Court Justice.
If she'd gotten her way, she may have never ascended to the top eschelon of the legal profession.
Kagan clerked for legendary Chicago federal Appellate Judge Abner Mikva, who is one of Obama’s political mentors. She went on to have a brilliant scholarly career.
"Her credentials were just incredible. She was one of the brightest kids in the class. The professors I talked to said she's smart, she's hard-working, she understands what the law is about, and they were right -- she was one of the best clerks I ever had," Mikva said on MSNBC Monday afternoon.
Kagan laid the groundwork for many of her political beliefs while at the University of Chicago, and perhaps provided fodder for Republicans to interrogate her.
Before winning tenure at the University of Chicago she published Confirmation Messes, Old and New a review of a book about the judicial confirmation process.
Kagan lamented the lack of "seriousness and substance" in confirmation hearings for Stephen Breyer and Ruth Bader Ginsburg. "When the Senate ceases to engage nominees in meaningful discussion of legal issues, the confirmation process takes on an air of vacuity and farce," she wrote in the University of Chicago Law Review in 1995.
Asked about this by senators when her nomination as solicitor general was pending, Kagan replied that she is "less convinced than I was in 1995 that substantive discussions of legal issues and views, in the context of nomination hearings, provide the great public benefits I suggested."
But Supreme Court hearings are a different beast, and because she has a limited paper trail with which to judge her substance her words may come back to haunt her. Kagan has never served as a judge.
She would be the first person in 38 years to join the Supreme Court without first serving as a judge.
Then again, Kagan is used to firsts.
She was the first female dean of Harvard Law School, where she made a reputation for bringing together liberals and conservatives on Harvard's notoriously fractious law school faculty.
She’s the first female Solicitor General and would be only the fourth woman to serve on the Supreme Court.
Last year, the Senate confirmed Kagan by a vote of 61-31, with only 7 Republicans supporting her. The relatively large number of votes against her cheered some conservative activists, although the margin suggested Kagan would again prevail in a confirmation vote for the Supreme Court.
Kagan's fate will be up to a Senate dominated by Democrats, who with 59 votes have more than enough to confirm her, even though they are one shy of being able to halt any Republican stalling effort.
For the second straight summer, the nation can expected an intense Supreme Court confirmation debate even though, barring a surprise, Kagan is likely to emerge as a justice.
Supreme Court justices wield enormous power over the daily life of Americans. Any one of them can cast the deciding vote on matters of life and death, individual freedoms and government power. Presidents serve four-year terms; justices have tenure for life.
Republicans have shown no signs in advance that they would try to prevent a vote on Kagan, but they are certain to grill her in confirmation hearings over her experience, her thin record of legal writings and her objections to the military's policy about gays.
Being old-time Chicago-friends with Obama might not sway Republicans to her side either.
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