That would pay as well as the foundation and offer more freedom to keep his hand in politics.
Obama spent the first few months after the primary stewing over his defeat. Once he got over it, he realized that if he was going to have a political future, he would have to repair his relationship with the black community. Bobby Rush’s crowd—the nationalists, the militants, the folks who wanted to rail against the white man—would never embrace him now. During the campaign, Obama had made it clear he considered their brand of politics self-defeating.
“On issues of job creation, education, health care, we have more in common with the Latino community and the white community than we have differences,” he’d said. “And we have to work with them, just from a practical political perspective. It may give us psychic satisfaction to curse out people outside the community and blame them for our plight, but the truth of the matter is if we want to get things accomplished politically, then we’ve got to be able to work with them.”
There was a segment of black Chicago that was ready to hear Obama’s vision of pan-racial politics: the business community. Although Obama was not wealthy—at best, the family was upper-middle-class—he already socialized with members of the city’s black bourgeoisie. John Rogers was a close friend, as was Marty Nesbitt, a vice president of the Pritzker Realty Group. (Nesbitt’s wife, an obstetrician, delivered both of Obama’s daughters.) Obama was also a member of the East Bank Club, a downtown gym/networking salon popular with Chicago’s professional class. He played pickup basketball with Jim Reynolds, CEO of Loop Capital Markets, an investment banking firm. Reynolds knew only that Obama was a state senator, which wasn’t enough to impress him. Then, one day, he was browsing at Borders and found Dreams from My Father in the discount bin. Surprised that one of his basketball partners had written a book, Reynolds bought a copy. The next time he saw Obama on the court, Reynolds mentioned Dreams.
“Hey, you know, I read your book,” he told Obama. “You’re a pretty good writer. You had an interesting background.”
“Well, I know I’m a good writer!” Obama shouted back.
After that, Obama and Reynolds became regular teammates. They also met up for golf at the South Shore Country Club, where Obama always won by keeping the ball in the fairway and hitting no errant shots. When Reynolds was in Springfield, he used Obama’s state senate office as his own.
Reynolds, who was one of the buppies on the Obama for Congress finance committee, also helped Obama plot his next political move: a run for the U.S. Senate. On the night Obama lost to Rush, Reynolds tried to buck up his friend by assuring him there would be other races, for bigger offices.
“Hey, man, don’t feel bad,” he told Obama. “Let’s figure out what we’re going to do next.”
It wasn’t long before they did. Obama and Reynolds sat down with Marty Nesbitt and ran through the list of statewide offices. Attorney general would be open in 2002, but Obama’s fellow state senator Lisa Madigan had her eye on it. And Madigan was the daughter of the state’s most powerful Democrat, House Speaker Michael Madigan. The Senate looked more promising. The Republican incumbent, Peter Fitzgerald, was seen as a one-term fluke. Fitzgerald had not so much beaten Carol Moseley Braun (herself a one-term fluke) as been in the right place to benefit from her missteps. Once in office, he alienated his party by appointing a U.S. attorney from out of state. Unfamiliar with the Chicago Way, Patrick Fitzgerald (no relation) prosecuted corrupt Republicans and Democrats with equal ardor. Senator Fitzgerald had even tried to block funding for a new Lincoln museum in Springfield, figuring it was just pork for Governor George Ryan and his lobbyist pals. As a result, he had no friends in the Illinois GOP, and the word was he would either step down or face a primary challenge from a Republican more willing to play the game.
Reynolds began bringing Obama to meetings of the Alliance of Business Leaders and Entrepreneurs, an all-black business group that met for a monthly luncheon at the Chicago Club. Obama was one of the few politicians among a crowd of investors, bankers, publishers, and attorneys. Whenever anyone questioned his presence, Reynolds made one thing clear: “If you want to be a friend of mine, you have to be a friend of his.” While Obama never gave a speech at the ABLE