Young Mr. Obama (15 page)

(Making those nasty remarks was Trotter's job. He wasn't trying to win. He was a hatchet man. Emil Jones had put him in the race to split the anti-Rush vote.)

Alderman Toni Preckwinkle tried to help Obama connect to the streets. Preckwinkle held a grudge against Rush, because he had run several candidates against her in the last aldermanic elections. When Obama came to Preckwinkle's office to talk about running for Congress, she told him, “Look, I've tried to stay out of Bobby's way. I don't do him any harm. He sent all these people after me this time. I'll be happy to help you, but you've got to decide right away what to do and get going.”

Obama didn't make up his mind until the summer. Preckwinkle thought that was awfully late, but she still loaned him her chief of staff, Al Kindle, a veteran fixer who had begun his career organizing wards for Harold Washington. Kindle had actually met Obama back in 1985, when he was 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 on the day of the flight, Obama's eighteen-month-old daughter, Malia, came down with the flu. He decided to stay in Hawaii one more day. If Malia seemed to be recovering, the Obamas would fly home together. If not, Barack would fly out alone. Governor Ryan's office was frantically trying to get Obama back to Springfield, even offering him a private plane from Chicago. Obama sensed the vote was symbolic. Unless Republican senate president Pate Philip agreed to a compromise, the bill was going to flunk out of the senate and go back to committee for further negotiations. Despite that, Obama's presence was important to his political career. If you supported a bill, you couldn't skip the vote. Especially not for a Hawaiian vacation.

On Wednesday, December 27, Malia was well enough to fly, and the family returned to Illinois. (If they hadn't made that flight, they wouldn't have been able to get out until January 8.) The bill came up for a vote that day and failed by three votes. Obama was missing from the tally. Governor Ryan, grumpy even when he was in a good mood, was especially unhappy.

“I'm angered, frankly, that the senate didn't do a better job,” he said.

Shomon wasn't happy, either. He taunted his candidate with this vision of a negative ad: a man in a beach chair sipping a mai tai as ukulele music played in the background and a deep-voiced narrator sneered, “While Chicago suffered the highest murder rate in its history, Barack Obama…”

Obama never apologized for putting his daughter's health above politics. Once he got back to Chicago, he called Abner Mikva, who supported his decision.

“Barack,” Mikva said, “when I was in Congress, there were times when you don't want to, but your family is an issue, and we put our families through so many things, so many sacrifices in this process, anyway, that every once in a while, we have to make decisions in terms of what you think is best for your family, and I think that this was one of those decisions.”

Even more than the murder of Bobby Rush's son, the Safe Neighborhoods Act vote convinced Obama that his campaign was a lost cause.

“Each morning from that point onward I awoke with a vague sense of dread,” he would write in
The Audacity of Hope
, “realizing that I would have to spend the day smiling and shaking hands and pretending that everything was going according to plan.”

Obama's opponents didn't need to run that Hawaiian ad. The callow state senator was castigated in the
Tribune
's “Inc.” column (the headline:
D-U-M
) and by callers to WVON. He had to answer for his missed vote during a candidates' forum with Trotter in the dank basement of a park field house.

“If you initiate a lot of ideas and at the time of a vote you're not there, how can we count on you?” a voter asked.

Obama answered curtly. “If you look at my record in Springfield, I don't miss votes. I missed one as a result of my daughter being sick. That's an exceptional situation that doesn't arise often.”

The man didn't buy Obama's excuse.

“If you tell me this is one of your issues, and then you miss the vote, that concerns me,” he said afterward. “With that in mind, I'm very reluctant to support him for anything. I think he's biting off a little more than he can chew. He's got some good issues, but he's too green.”

That was the debate where Obama finally lost his cool. Even his body language signaled it. He sat with his lanky legs crossed, chin cocked at a heroic angle. He wasn't even trying to conceal his impatience with Trotter, a mere state senate peer, or with this grungy necessity of campaigning.

Trotter was a traditional Chicago politician, a cloakroom operator who knew how to pass a bill. He liked to brag about the pork he brought home to his district—$26 million for a library at Chicago State University, $75 million for resurfacing Lake Shore Drive. He'd been an architect of the state's child health care system. Like many senators, Trotter thought Obama considered himself too cool for the chamber and disdained the hard work of digging up votes. That evening, he shared his perception with the voters in the folding chairs. Trotter hunched over his microphone, taking digs at his increasingly irritated rival. When he needled Obama for failing to corral enough votes to override Ryan's veto of the child support bill, Obama's calm finally dissolved.

“Senator, that's a distortion!” Obama snapped. His baritone went full fathom five, but he never unbent from his patrician pose.

When I interviewed Obama at his downtown law office, in early February, his answers only reinforced the accusation that he was arrogant. Obama had always seen himself as a special figure, bound for a bigger destiny than the people around him. In
Dreams from My Father
, even the portraits of his family members—a dreamy, hippie-ish mother, an ineffectual grandfather—were a little patronizing. He
was
bound for a big destiny, but that's no way to portray yourself to the voters, especially in one of the nation's poorest congressional districts.

Obama had been a golden boy for so long: embraced by the Ivy League, profiled in the
New York Times
, a published author at thirty-four, a state senator a year later. For the first time in his life, his ambitions were being blocked. The world was pushing back. His impatience showed in a condescension to his surroundings.

Why, I asked him, should the voters choose a newcomer to the South Side over two men who had grown up in Chicago?

Obama struggled for an answer, then joked that his willingness to move from Balmy Hawaii to frozen Chicago showed he was more committed to the city than many natives.

“I really have to want to be here,” he said. “I'm like a salmon swimming upstream in the South Side of Chicago. At every juncture in my life, I could have taken the path of least resistance but much higher pay. Being the president of the
Harvard Law Review
is a big deal. The typical path for someone like myself is to clerk for the Supreme Court, and then basically you have your pick of any law firm in the country.”

Didn't the people appreciate the sacrifices he'd made? To grind out a voter registration drive when he could have been earning $200K a year at a white-shoe firm? To pick his way over an ice-glazed Chicago sidewalk when he could have been bodysurfing back home in Honolulu?

Bobby Rush understood the struggles and aspirations of the high school dropout or the hotel maid trying to raise three children in a way that was impossible for Obama. Obama's blackness had been an advantage with his
Law Review
colleagues and his New York publisher. Rush's blackness had been another handicap to overcome, like his stutter or his poverty.

When Rush was invited to speak from the pulpit of Southwestern Baptist Church, on South Michigan Avenue, he urged the congregation to buy computers and hook up to the Internet, so knowledge would flow into their homes. Using his seminary training, he made a religious connection for his audience, comparing the Web to the Gutenberg Bible, which allowed all Christians to read what only the “high-class, super-elite” priests had seen.

“At one time, the Bible was only read and understood by a very few people,” Rush told his listeners. “These folks intimidated those that didn't have access to the Bible. God in his wisdom created the printing press. Then the Bible was mass-produced, so common ordinary folk snatched the power from the elite. I look at the Internet the same way. If we are computer literate, we are on the same level as Bill Gates, the richest man in the world. We are on common ground with the wealthy and powerful. You can bring the libraries of the world to your living room, whether your living room is on South Michigan Avenue or in the richest suburbs.”

Obama had gotten some good press for a proposal to spend $50 million on computers for South Side schools, but he'd never expressed the need that eloquently, in the language of black empowerment.

Rush's success in the churches—he held a “Clergy for Rush” rally at which over a hundred ministers gathered in front of a
WE ARE STICKING WITH BOBBY!
banner—revealed another of Obama's miscalculations. He had assumed that Rush's mayoral defeat meant he was vulnerable in his congressional district. But Rush was clobbering Obama for the same reason he'd lost the mayoral race—he was a South Sider to his bones. Rush had flopped as a citywide candidate because he couldn't see beyond the needs of his community. As a congressman, he didn't have to.