working for a gang prevention project that started an after-school program in Altgeld Gardens. Back then, Kindle had been a bigger deal on the South Side than this skinny organizer all the old ladies loved. They’d all said Obama was going places, but Kindle hadn’t seen the potential. Not at the time.
Now that he was working for Obama, Kindle saw it as his job to defend the man’s blackness. Kindle was a big blood: nearly a head over six feet tall, with the girth of a man who ate an entire plate of chicken wings as an appetizer. He’d worked with gangs for a dozen years, so he was cool walking into Stateway Gardens or the Robert Taylor Homes. Kindle thought of himself as the street heat, “Darth Vader,” the man who knew where the gangs hung out, where the drugs were sold, which cops were on the take. His job, as he saw it, was to make sure the word “defeat” wasn’t chiseled on a candidate’s tombstone.
When Obama marched in the Bud Billiken Parade—the largest African-American parade in the country and an essential appearance for any South Side politician—Kindle rounded up fifteen supporters to march alongside him. In the projects, he heard the questions that Rush and Trotter were trying to raise.
“Who is this African?”
“Does he live in the neighborhood?”
“Is he tough enough?”
“Is he controlled by the white man?”
“Can we trust him?”
Kindle had the same answer for every question.
“If you trust me, vote for him.”
Obama made Kindle’s job difficult. He was an inexperienced candidate who thought he could win by showing the voters his brilliance, as though he were still running for president of the Harvard Law Review. He just couldn’t—or wouldn’t—loosen up. The dignified demeanor that had won him a state senate seat in Hyde Park did not translate to the district’s inner-city precincts. His internal rhythm was set to “Pomp and Circumstance.” At a nightclub called Honeysuckle’s, Obama held an event for black teachers, where he defended his education.
“When Congressman Rush and his allies attack me for going to Harvard and teaching at the University of Chicago, they’re sending a signal to young black kids that if you’re well educated, somehow you’re not ‘keeping it real,’ ” he told his listeners.
The air quotes hung over the silent room.
Obama was simply too inhibited, too embarrassed, to force out phrases like “our community,” which rolled naturally off the tongues of Rush and Trotter. Al Kindle and Ron Davis got so fed up with Obama’s stiff public speaking they tried an intervention. You’re giving a lecture, they told him. The purpose of a lecture is to communicate information clearly so students can take notes. That’s not a campaign speech.
Obama brushed off the advice.
“Blackness is not based on what you say,” he told his advisers. “It’s based on what you do.”
Davis thought that was an arrogant statement.
“Motherfucker, you ain’t goin’ anywhere,” he taunted Obama. “You ain’t gonna get elected dogcatcher. You’re full of yourself. You have to let the air out.”
Obama was uptight for another reason. He knew he was going to lose.
Obama had sabotaged his campaign when he failed to come home from a Hawaiian vacation to vote on the Safe Neighborhoods Act, a bill that would have made unlawful possession of a loaded firearm a felony. Obama’s vote wouldn’t have made a difference, but he had been a strident supporter of gun control, so a lot of Chicagoans thought he was absent when his voice was needed most. Once a year, Obama took his family to Hawaii to visit his grandmother Toot. In 1999, he almost canceled the trip because the fight over the Safe Neighborhoods Act went on until December 22. The Obamas managed to get out of town on Thursday, December 23, and planned to fly back the following Tuesday, so Obama could be in Springfield when the legislature reconvened the next day.
Kindle, who didn’t understand that Obama’s grandmother was the only matriarchal figure in his life, had tried to talk him out of flying to Hawaii in the middle of a congressional primary. Michelle wanted to go, Obama insisted. That was a difference between Obama and Harold Washington, Kindle came to realize. Washington was a political automaton with no family, no personal life, and no friends outside Chicago.
On the Monday after Christmas, Obama called Dan Shomon to find out whether Governor Ryan was planning to call the legislature back into session. The governor was, Shomon said.
“We’re going to have to go back early,” Obama told Michelle.
But