happened to be a Chicago police officer. The state’s attorney set up a phone-sex sting. While sitting in a prosecutor’s office, the girl called Reynolds and told him she couldn’t make their tryst because she had to babysit.
“What you gonna wear?” Reynolds asked.
“Well, my peach underwear, like you told me to. I was hoping we could do something really special but I see that’s not going to happen, I guess.”
“I was definitely gonna fuck,” Reynolds said.
“Really?”
“Right in my office. I was gonna masturbate too.”
At the panting congressman’s urging, the girl spun a story of sex with a lesbian lover. When Reynolds asked if the other woman would be willing to do a threesome, the girl said no—but she knew a fifteen-year-old girl who might. A fifteen-year-old Catholic schoolgirl.
“Did I win the lotto?” Reynolds exclaimed.
There was no fifteen-year-old schoolgirl. But Reynolds’s declaration of his lust for teenagers turned into a catchphrase. Jay Leno joked about it on The Tonight Show. The case was so salacious it made headlines in Chicago for more than a year. Reynolds won reelection in his heavily Democratic district, but by 1995, he was facing a trial that threatened to cost him his seat in Congress.
Reynolds’s downfall was so distressing because he wasn’t supposed to be another Chicago pol. His election had represented the same sort of postracial promise and generational change that Obama’s would a dozen years later. Born in Mississippi, raised in a housing project, Reynolds had attended Harvard and won a Rhodes Scholarship. After two failed primary runs, he finally unseated Representative Gus Savage, a crude black nationalist who campaigned by reading aloud lists of Reynolds’s contributors, lingering over the names of Jews.
Reynolds protested that he was only guilty of phone sex and erotic fantasies, but as his trial approached, a challenger stepped forward. State Senator Alice Palmer announced she would run against Reynolds in the Democratic primary the following March. Palmer’s seat was up for reelection in 1996, so, win or lose, she would be leaving the legislature. As a middle-aged woman, Palmer figured to be an appealing candidate against a congressman caught in a sex scandal. She immediately won the support of EMILY’s List, which donates to female politicians around the country.
Palmer’s state senate district included Hyde Park, so this was Obama’s chance.
“If Alice decides she wants to run, I want to run for her state senate seat,” he told his alderman, Toni Preckwinkle.
Obama also discussed his ambitions with Jesse Ruiz, his old law school student. The two were now friends, sharing an annual summer luncheon. In 1995, Ruiz brought a copy of Dreams from My Father for Obama to sign.
“You’re the only guy I know who wrote a book,” Ruiz said. “Who knows? You might make something of yourself someday.”
That day was now, Obama told Ruiz. He laid out a plan for a political career that would begin in the state senate and culminate with his election to Harold Washington’s old job.
“I’m going to need help from you,” Obama said earnestly.
“Barack, Mayor Daley is going to be there forever,” Ruiz said, scoffing. But he agreed to work on Obama’s senate campaign. A state senate seat seemed achievable. Ruiz held a small fund-raiser in the apartment of his then-girlfriend (now his wife), raising $1,000.
Around this time, Obama had dinner with Douglas Baird. Now dean of the law school, Baird took Obama to the Park Avenue Café, a fancy downtown restaurant. The dean had woo on his mind. He wanted Obama to become a full-time assistant professor and dedicate himself to law teaching and academic writing.
During the meal, Baird asked Obama about his law school grades. Obama, who took his intellectual image seriously, shot Baird an irritated look. Wasn’t a Harvard degree proof enough that he knew the law?
“Douglas,” he said, “I graduated magna.”
So Baird offered him a job.
“Barack, I’d like you to become a full-time academic,” Baird said, “but you have to understand, if you become a full-time academic, you have to seriously commit yourself to academic scholarship. There’s no sense getting into something if you don’t have relatively clear expectations.”
“Douglas, that’s not me,” Obama said.
Obama enjoyed teaching, but he didn’t see himself as someone who wrote academic papers or attended conferences where scholars critiqued the works of Richard Posner. It was too far removed from real life. He was going into politics, he told Baird. He was running for the state senate. Obama even asked Baird for a donation. Baird wrote him a check but found it amusing that at one