Among prominent federal appeals court judges in the 1990s, Barack Obama was known as "the one who got away."
In 1990, Obama had been elected the first African-American president of Harvard Law Review, which made him a blazingly hot prospect as a law clerk for one of the top federal appeals judges, who in turn would almost certainly send him on to the Supreme Court as a clerk.
But with a remarkable certitude that still amazes his friends and elders, Obama said no to all that, preferring to return to Chicago after graduating in 1991 to resume community and civil rights work and to write a memoir that turned into a best-seller, "Dreams from My Father." Now, only 16 years later, the junior Democratic senator from Illinois is a top contender for the presidency of the United States.
Eschewing a possible Supreme Court clerkship could stand as Obama's biggest "road not taken," a decision that would have taken him on a path toward a top law firm, law school faculty, or judgeship.
Instead, Obama plunged into Illinois politics, charting a trajectory that could put him in the position of appointing Supreme Court justices as president -- or, in an alternative scenario floated recently by The New Yorker's Jeffrey Toobin and the Chicago Tribune's Clarence Page, serving on the Supreme Court as Hillary Clinton's first appointee.
"He had a lot of chutzpah, doing what he did," recalled Abner Mikva, who actively pursued Obama as a possible clerk when he was chief judge of the U.S. Court of Appeals for the D.C. Circuit.
Mikva, a former Democratic congressman with his own Chicago roots, ended up a good friend and mentor to Obama and is an active supporter of his presidential bid. "I often tease him about how he could have been a clerk for me," says Mikva, now 81 and on the University of Chicago Law School faculty. Of Obama, Mikva says, "I have not been this impressed by a political talent since the day I saw FDR in a parade as a boy."
REJECTING THE OBVIOUS PATH
Obama's election to the top spot at Harvard Law Review was intensely competitive, and some profiles portray him as reluctant to join the race precisely because it was viewed as a ticket to clerkships followed by a career at a big law firm, which he did not want. Once he decided to take the plunge, Obama campaigned with gusto against 19 other candidates. His win garnered national headlines and a book deal.
Apart from the hoopla, Obama's professors saw in him a talented legal mind and an ability to unify students.
Harvard law professor Laurence Tribe, who counts Obama as one of his best students in his career on Harvard's faculty and is an adviser to Obama's campaign, says Obama would have been a great law clerk for the high court. "But I knew he was committed to public service in Chicago," Tribe says. That commitment was pulling him away from the clerkship path.
Word of Obama's talents spread fast among the "feeder" judges who supplied the high court with its elite clerks. Attention had not yet been drawn to the dearth of minorities among Supreme Court clerks, but at least some of the appellate judges were on the lookout. "I was always trying to get more minority clerks," says Mikva.
So Mikva asked Sheryll Cashin, one of his clerks at the time, to invite Obama for an interview in 1990. Cashin, now a Georgetown University Law Center professor, had met Obama while she was in her final year at Harvard and Obama was in his first.
She remembers attending a Black Law Student Association reception for new students, where, she says, "a lot of first-year females were hanging on his every word, and I was, too." Obama was 27 when he entered law school, and though he was "shabbily dressed," in Cashin's words, "he was charismatic. People were just drawn to him."
When Cashin called Obama on Mikva's behalf, she expected to snag him for a clerkship with relative ease. "Judge Mikva had one of the highest batting averages for sending his clerks to the Supreme Court the following year."
But when she reached Obama by phone, it turned into "a call I will never forget," says Cashin. He said no, telling her about his plans to return to Chicago. "I was blown away," says Cashin. "This was unheard of." He was turning down money as well as prestige, she notes. "Back then, there was a hiring bonus at firms for clerks of about $35,000." (Now that bonus for Supreme Court clerks tops $200,000.)
"I don't know anyone with the fiber not to take that opportunity," says Cashin admiringly. "He had a clear vision of what he wanted to do. That's an incredible testament to his character."
Bruce Spiva of Washington, D.C.'s Spiva & Hartnett, a second-year student on the law review when Obama was president, also recalls the reaction when word spread that Obama had rejected clerkship opportunities. "That was the great ambition of so many of our cohorts, and he could have had his pick," says Spiva. "It might have been hard for some to understand."
But people respected his choice, Spiva recalls. "He wanted to do politics. He had other things on his mind."
(Obama could not be reached for comment for this article.)
Tribe also recalls when Obama came to him and said, "Professor Tribe, I've decided pretty much not to take a clerkship." Other professors had urged Obama to pursue a clerkship, but Tribe says he was not among them. "Given Barack's maturity and aspirations, I thought the benefits of progressing straight toward his goals without making a detour for two years of clerkships outweighed the costs."
Tribe has campaigned for Obama this fall, making appearances in Iowa and New Hampshire. "I've never done this before in my life. It's been terrific."
Reflecting on what might have happened if Obama had gone the clerkship route, Tribe says Obama might well have returned to Chicago anyway and taken a similar path -- but two years later.
And that, says Tribe, might have made all the difference in the world.
"He would be on a different cycle," says Tribe. "But this moment, right now, is so exquisitely right for him and for the nation -- not two years from now."