For Barack, it’s not a constant flow of glorious defeats. He has good attention to ideals and core principles, but a recognition that it is good to get things done from year to year.
—JOHN BOUMAN, ANTIPOVERTY ADVOCATE
For the first six of Barack Obama’s almost eight years in the Illinois General Assembly, he suffered from an aggressive legislator’s most debilitating affliction—membership in the minority party. In national politics today, Illinois is a pure blue state, considered an immediate loser for a Republican presidential candidate. But Illinois voters have a long history of electing moderate Republican governors, as well as turning over state legislative chambers to the Grand Old Party. Rural areas of Illinois are known for sending Republicans to the state legislature, as are the suburban counties that encapsulate Chicago. The Illinois House of Representatives has been dominated by Democrats for some time, but Republicans captured control of the Illinois Senate in 1992 and held on to it for a decade.
No red carpet unfurled for Obama when he arrived in the state capital of Springfield in January 1997. If anything, his fellow senators cast a cold eye. Many of his colleagues viewed him in the same visceral way that his aide, Dan Shomon, first reacted to him: Here comes an aloof Ivy League good-government type who too often mentions his years of sacrifice as a community organizer and his Harvard Law pedigree. “The fact that he had a Harvard Law degree and was a constitutional law professor—that made some eyes roll,” said Kirk Dillard, a Republican senator from suburban Chicago.
Despite his time organizing the poor on the city’s Far South Side, Obama’s ability to connect on a broad scale with urban blacks outside his collegial Hyde Park neighborhood was highly questionable. And even though he had spent several years as an organizer in the city’s economically depressed communities, he exhibited far more comfort in university-type settings where he could woo the white lakefront liberal set—environments that highlighted and celebrated his cerebral, mission-oriented, policy-wonk nature. His public speeches tended to be policy-heavy and overly intellectual—fine for Harvard Law students, but fairly dry for everyday people. Indeed, some of his senate colleagues, especially in the Legislative Black Caucus, saw in him an Ivy League elitist unwilling to sully himself with the unseemly universe of Chicago ward politics or the muck of the legislative process. “It wasn’t like Barack took Springfield by storm,” Shomon said. “The first few years he was thought of as intelligent, thoughtful, bright. But he certainly wasn’t considered to be a major player.” Rich Miller, the publisher of Capitol Fax, a statehouse newsletter, was less diplomatic. “Barack is a very intelligent man,” Miller said in 2000. “He hasn’t had a lot of success here, and it could be because he places himself above everybody. He likes people to know he went to Harvard.”
Miller’s characterization might be unduly harsh, but in charitable terms, Obama initially toiled in relative obscurity in the statehouse. His intellectualism initially did not translate well to Springfield, where most grunt legislative success is accomplished over spirits in a local tavern or between iron shots on the fifth fairway. In addition, Obama’s palpable disdain for some of the petty antics of his fellow legislators did not endear him to those colleagues. At the same time, Springfield had its share of self-absorbed, monosyllabic hacks with little use for an urbane sophisticate like Obama.
Nevertheless, with Shomon as his main tutor, Obama eventually adapted to this environment. He picked up golf. He established close working and personal friendships with a number of fellow legislators, and these associations would greatly assist him as his political career unfolded. By the time his tenure in Springfield ended, it could be argued that he had evolved into a very successful state lawmaker. Viewed warily by some of his fellow blacks, Obama primarily formed alliances with downstate Democrats and a handful of Republicans. These friendships would show that while some people, especially some blacks, regarded Obama as elitist, he could mix with other everyday legislators quite comfortably.
Perhaps most significantly, Obama joined a weekly poker game that included fellow senators Terry Link and Denny Jacobs, white Democrats who represented districts outside Obama’s home base of Chicago. The son of a man who studied economics at Harvard, Obama was not surprisingly a skilled poker player. As when playing board games at home, the highly competitive Obama took the game seriously. He played carefully and was adept at not revealing his hand. Senator Link joked that Obama took his money at the card table and Link won it back on the golf course, where Obama was still learning the game.
The loose poker atmosphere, however, did not always fit with Obama’s exceedingly strict sense of propriety and morality, traits instilled primarily by his mother. During one poker game, Obama was irked when a married lobbyist arrived with an inebriated woman companion who did not acquit herself in a particularly wholesome fashion. Without offending his buddies, Obama registered his displeasure with the situation. “He didn’t think much of that,” an Obama associate said. “He didn’t see the purpose of bringing her.”
Legislatively, Obama managed to pass a decent number of laws for a first-term lawmaker in the minority party. His first major legislative accomplishment was shepherding a piece of campaign finance reform in May 1998. The measure prohibited lawmakers from soliciting campaign funds while on state property and from accepting gifts from state contractors, lobbyists or other interests. The senate’s Democratic leader, Emil Jones Jr., a veteran African-American legislator from the South Side, offered Obama the opportunity to push through the bill because it seemed like a good fit for the do-good persona projected by Obama. Obama was also recommended to Jones by two esteemed Chicago liberals who had taken a liking to him: former U.S. senator Paul Simon and former congressman and federal judge Abner Mikva. Working the bill was an eye-opening experience for the freshman senator. It was a tough assignment for a new lawmaker, since he was essentially sponsoring legislation that would strip away long-held privileges and perks from his colleagues. In one private session, a close colleague angrily denounced the bill, saying that it impinged on lawmakers’ inherent rights. But Obama worked the issue deliberately and delicately, and the measure passed the senate by an overwhelming 52–4 vote. “This sets the standard for us, and communicates to a public that is increasingly cynical about Springfield and the General Assembly that we in fact are willing to do the right thing,” Obama told reporters immediately after the bill’s passage. The bill was not a watershed event anywhere but Illinois. It essentially lifted Illinois, a state with a deep history of illicit, pay-to-play politics, into the modern world when it came to ethics restrictions. The bill gave Obama a legislative success, but his public criticism of Springfield’s old-school politics did not sit well with some of his colleagues, who already considered the Ivy League lawyer overly pious.
Furthermore, this highly publicized success stood rather alone. Obama was learning that, like the court system, the legislative branch of government could move at a snail’s pace. Indeed, as his time wore on in the minority party, he became increasingly frustrated by the workings of the Illinois legislature. He was especially irritated that too many grandstanding, feel-good measures seemed to go forward easily, while bills that offered structural change were bottled up in committee or never got off the ground. For instance, lawmakers easily passed a bill that strictly outlawed graffiti painting, but were reluctant to take on deeper juvenile justice issues. The graffiti bill garnered its sponsors a political gold mine of media attention.
IN SPRINGFIELD, OBAMA RAN INTO SOME OF THE SAME ISSUES WITH blacks that he experienced at Harvard. He was not shy about criticizing black leaders and their legislative strategy; also, he did not necessarily follow his caucus’s talking points. Moreover, he worked closely with white Democrats and even conservatives to pass his own bills. Obama, to be sure, had allies in the black caucus, but he had his share of critics as well. His chief antagonists were Rickey Hendon, who represented a district on the city’s West Side, and Donne Trotter, who would run against Obama for Congress.
Hendon and other African-American lawmakers from the West Side often found themselves at odds with their South Side brethren, but the rift between Hendon and Obama was particularly acute. Hendon and Trotter would “just give Barack hell,” said Senator Kimberly Lightford, an Obama ally in the black caucus. Hendon, nicknamed “Hollywood” because he once aspired to produce films, was a flamboyant personality in Springfield, known for his smart-aleck humor and occasionally inappropriate public manner. In one legislative session, the two nemeses nearly came to physical blows when Obama, apparently inadvertently, voted against a bill that included funding for a project that assisted Hendon’s district. Years later, details of the incident remain in the eye of the beholder. Obama supporters say that Obama had stepped away from his seat and asked someone else to vote for him, not an uncommon practice considering the thousands of votes cast each session. His proxy, however, accidentally voted against his wishes. When Obama asked that the record reflect that he voted the wrong way, Hendon publicly accused Obama of duplicity. Hendon has never been shy about holding back his feelings, and he had a special way of penetrating Obama’s usually smooth exterior. Soon, the two men were shouting at each other on the senate floor. They took their disagreement into a nearby room, and a witness said that Obama had to be physically restrained. Neither man cares to discuss the incident today, but Hendon remains unconvinced of Obama’s explanation that his vote was accidental. Individuals close to the situation say Hendon still believes that Obama voted against his project in order to pacify North Side fiscal conservatives who were leery of some West Side projects. For his part, the rarely reticent Hendon won’t discuss the altercation, except to confirm that it occurred. “I have been advised to leave Barack alone and that is what I am going to do,” Hendon said. “I am going to let things stay in the past. It happened. That’s all I can say. It happened.”
Though Obama alienated some colleagues like Hendon and gained scant public attention, he nevertheless accrued a rather impressive record as a first-term legislator for the out-of-power Democrats. Much of it was like his community-organizing success—low-key and behind the scenes. In his first two years, Obama introduced or was chief cosponsor of fifty-six bills, with fourteen of them becoming law—not bad rookie and sophomore seasons. Besides the campaign finance and ethics bill, other Obama-led legislation that became law included measures that compensated crime victims for certain property losses, prevented early probation for gun-running felons, streamlined administrative processes when municipalities adjudicated ordinances and increased penalties for offenders who used date-rape drugs on victims.
In his third year, 1999, Obama was even more successful. He cosponsored almost sixty bills and eleven became law. They included measures that established a state-funded screening program for prostate cancer (a disease that disproportionately afflicts blacks), provided a training program in the use of heart defibrillators, strengthened hospital testing and reporting of sexual assaults, increased funds for after-school programming, increased investigation of nursing home abuses and hiked funding for lead abatement programs (another large issue in the black community).
Most of Obama’s legislative efforts were rooted in his discussions with special interest groups, and he was particularly attentive to activists who sought his help for a cause he supported, such as fighting poverty or protecting civil liberties. Yet he declined to take up issues simply for the sake of garnering attention. He was highly results-oriented. “Obama is interested in sponsoring bills that will pass and is [uninterested] in symbolic legislation,” Don Wiener, an opposition researcher hired by two later campaign opponents, wrote in a report assessing Obama’s early senate career. “He does not seem to sponsor legislation just because he is encouraged to do so.” Obama concentrated his efforts on pursuing legislation that reflected his basic sense of social justice. “He is idealistic but practical,” said John Bouman, a director of the Chicago-based National Center on Poverty Law. “For Barack, it’s not a constant flow of glorious defeats. He has good attention to ideals and core principles, but a recognition that it is good to get things done from year to year. He is willing to hammer out a good compromise, but he doesn’t compromise for the sake of it.”
A major reason for his high rate of bill passage was his deftness in reaching across the aisle to Republicans. After working in peace with conservatives on the Harvard Law Review, Obama was not the least bit uncomfortable taking the concerns of Illinois conservatives into account and placating their fears. His relentlessly polite, inoffensive manner was key to his success in this regard. “I always found him to be a true gentleman in all the negotiations and dealings that I had with him,” said Joe Birkett, a hard-nosed Republican prosecutor in conservative DuPage County who was Obama’s ideological opposite.
In the course of his legislative career, Obama persuaded Republicans to go along with an array of initiatives, winning bipartisan support on potentially polarizing legislation like reforming welfare and battling racial profiling by police. “The most important thing that you do in Springfield is you bring all sides of an issue to the table and you make them feel they are being listened to,” said Obama, hearkening back to lessons learned as a community organizer. This reasonable tone and genuine attentiveness to Republican concerns made Obama a key swing legislator for both Republicans and Democrats, even if his voting record was decidedly liberal. “Members of both parties listened closely to him,” said Dillard, the Republican senator from suburban Chicago who frequently cosponsored legislation with Obama.
AS OBAMA’S FIRST TERM WOUND DOWN, HE MADE HIS FIRST MAJOR political miscalculation. The cause of this misjudgment: unbridled ambition.
Obama had returned to Chicago from Harvard Law with an eye on the mayor’s office after witnessing Harold Washington’s historic tenure at city hall. But while Obama was away, Richard M. Daley, the son of iron-fisted longtime mayor Richard J. Daley, had brokered a peace with the black community and won the city hall job. By 2000, Daley had built a massive political army and held such a firm grip on the city council that unseating him looked akin to dethroning a king.
So Obama looked at Congress instead, deciding to challenge Representative Bobby Rush in the 2000 Democratic Primary. To Obama, Rush looked vulnerable in his South Side district. Rush, in fact, had tried to oust Daley in 1998—but he was stomped by the mayor. For this reason, Obama saw Rush as an aging politician ready to be replaced by a younger man with a fresh vision and new enthusiasm for tackling the ills of the black community. Obama figured that if he could spread his message of community empowerment and social justice, he could upend Rush. This was a circle-of-life philosophy, since Rush had won his seat in Congress in 1992 in exactly that fashion. Rush had alienated some Democrats by unseating a well-regarded black congressman, Charles Hayes, who needed just one more term to earn a comfortable pension. Despite this political history, Rush was not the least bit understanding of Obama’s challenge.
Through the 1990s, Rush had been neither a stellar success nor a failure in Congress—he had just sort of existed comfortably inside the Beltway. This was a bit surprising considering his somewhat radical past, which had gained him star status with black voters. Rush was a 1960s civil rights veteran, having been a member of the Student Non-Violent Coordinating Committee and an acolyte of the outspoken Black Power advocate Stokely Carmichael. After coming under the influence of Carmichael, Rush left SNCC and served as head of the Illinois Black Panther Party, whose mantra was “Power to the People.” The Panthers’ philosophy was in direct contradiction to the nonviolent tenets of SNCC, and they derived power from fiery eye-for-an-eye rhetoric and from arming themselves to defend against white-led urban police forces, most notably in Chicago and Los Angeles. After the Panthers faded from the public scene, Rush became a Chicago alderman in the Harold Washington era, and he served as one of Washington’s lieutenants on the city council.
With this history, Bobby Rush had the consummate résumé for a black politician representing a black congressional district. Indeed, the most enduring image of Rush remains a photograph of him as a Black Panther, clad in a black leather jacket and clutching a rifle.
So when thirty-eight-year-old Obama made a run at fifty-three-year-old Rush, the black political world did not embrace him. For the most part, blacks wondered what Obama was doing trying to unseat this black elder statesman; and some African Americans privately began to question not only Obama’s motives but his black credentials.
This questioning of Obama’s blackness gained some resonance for several reasons. Primarily, this came about because Obama had not been brought up in a traditional African-American setting. He had been active in Chicago’s poor black neighborhoods for a few years, sure, and that had gained him some street credibility. But that was nothing compared to being a former Black Panther and one of Harold Washington’s trusted foot soldiers. Obama was a beneficiary of the work by Rush and others to advance the black cause. And his running against Rush raised questions that perhaps this young upstart was an ungrateful beneficiary of that labor.
Much of this sentiment percolated beneath the surface or among Chicago’s black nationalist crowd. That group largely consisted of an aging generation that vividly recalled the civil rights struggle, but it was still an influential voice in Chicago’s black community. The charge that Obama lacked black authenticity appeared in its sharpest form in a March 2000 story in Chicago’s alternative weekly tabloid, the Chicago Reader. Another candidate in the Rush contest, State Senator Trotter, viciously accused Obama of being secretly controlled by powerful white interests. Before long, that doubt was reverberating through segments of Chicago’s South Side black community. Feeding into this perception were Obama’s personal résumé, which included ties to two institutions of white power (Harvard and the University of Chicago), his lack of connection to the broader black community while growing up in Hawaii and his campaign’s substantial financial support from wealthy white liberals—people like Abner Mikva, a former federal judge, and Bettylu Saltzman, a former aide to Illinois senator Paul Simon.
In addition, Obama’s state senate district on Chicago’s South Side was undergoing a demographic and socioeconomic shift during this period, a trend that has continued into the 2000s. Once blighted areas just south of downtown were experiencing the first waves of gentrification. Obama had formed a political alliance with the local alderman, Toni Preckwinkle, and both politicians were the beneficiaries of substantial campaign donations from developers eyeing these suddenly attractive South Side areas. These financial donations were both a boon and a detriment to Obama. The campaign cash from developers helped him remain independent of the Daley political machine, but they also caused him problems with the older African-American nationalists. (One developer who actively courted Obama, Antoin “Tony” Rezko, would cause Obama significant problems in later years when Rezko was indicted amid a federal investigation of pay-to-play politics.) There was considerable tension among these new developers, some of whom were white, and longtime black activists in the area. And there was virtually no way to reconcile their interests. Trotter not too subtly raised these concerns when he told the Chicago Reader, “Barack is viewed in part to be the white man in blackface in our community. You just have to look at his supporters. Who pushed him to get where he is so fast? It’s these individuals in Hyde Park, who don’t always have the best interests of the community in mind.”
THE ACCUSATIONS OF BEING LESS THAN BLACK TOOK HOLD IN CIRCLES that were open to such talk. With this political history working against Obama in the black community, some of his advocates began wondering in earnest about his political strength among Chicago’s blacks. Said the Reader during Obama’s 2000 challenge of Rush: “There are whispers that Obama is being funded by a ‘Hyde Park mafia,’ a cabal of University of Chicago types, and that there’s an ‘Obama Project’ masterminded by whites who want to push him up the political ladder.”
Contributing to this perception was his loving treatment by the Chicago Tribune, the region’s most influential newspaper. The Tribune has historic ties to the Republican Party, and its readership is still disproportionately white compared with the diverse population it serves in the Chicago region. The Tribune, gushing that Obama was “a rising star in the Democratic Party,” endorsed Obama over Rush and Trotter in the 2000 primary race. Any black leader with the imprimatur of the editorially conservative Tribune had to be viewed with wary eyes on the South Side, where home-delivered Tribunes can go untouched for days while copies of the rival Sun-Times must be picked up from doorsteps early in the morning, lest they be swiped. “What was interesting,” observed Jerry Kellman, the Chicago community activist who brought Obama to Chicago, “Barack is in the black community and he is being attacked for not being black enough, not because he is half-white, but because he went to Harvard, and because he talks like he could be white and he moves like he does. There are thousands of black people who move and talk like he does, but they are not running for Congress from the South Side of Chicago.”
For his part, Obama maintains that the charge of not being black enough was little more than a canard drummed up by his political foes. “What’s fascinating is it’s never been an issue among regular folks on the street,” he said. “You know, it’s never an issue with the bus drivers or the teachers or the guys on the street corner who I’m talking to. This is always an issue that’s been brought up in the context of a political situation by professional politicians. And it’s a handy shorthand to try to create some separation between me and what’s a strong part of my base. But it really is not something that has ended up being a problem for me with respect to the voters.” Privately, however, Obama told me that he has encountered blacks who question his commitment to the black cause and his self-identified status as an African American. “What I’ve found,” he said, “is they are usually going through identity issues themselves and they project those issues onto me.”
The issue of Obama’s black authenticity would follow him from this time forward—rearing its head again in his race for the U.S. Senate and then again in his presidential bid. But it was in this congressional contest that it was first broached.
OBAMA’S CAMPAIGN FOR CONGRESS WAS STAR-CROSSED ALMOST from the very beginning.
On October 18, 1999, five months before the primary, Rush’s twenty-nine-year-old son, Huey Rich, was gunned down on a South Side street. For days, the Chicago media overflowed with the story of Rush’s son fighting for his life, spurred in no small part by public appearances of a solemn-looking Rush in which he talked about the incident. By the time Rich died four days later, the congressman had been transformed in the public eye from the 1998 mayoral candidate who had been thrashed by Mayor Daley into a grieving parent who had suffered the tragic loss of his son.
The death all but silenced Obama’s campaign. As he was trailing Rush badly in the polls (one survey found that Obama had only 9 percent name recognition in the district compared with the incumbent’s 90 percent), Obama’s only hope was to go negative on Rush. This was a strategy Obama had been considering before the shooting. Opposition researchers for Obama’s campaign had found that Rush’s relations with his grown son had been strained. Rush had fathered Huey in the late 1960s with Saundra Rich, another member of the Black Panthers. Rush, in fact, had named his son after Panther founder Huey Newton. But Obama’s research showed that Rush had touch-and-go involvement in his son’s upbringing, with Huey being raised primarily by an aunt. One of the men convicted of the shooting told police investigators that he sought out Huey because he believed the congressman’s son was carrying cash for a drug dealer.
If Obama were to unseat Rush, he would have to use something along these lines to portray Rush in a negative light. Now that Huey Rich had died tragically, that morsel of potentially negative information was off the table. Attacking Rush for being an absent parent now was completely out of the question. In fact, attacking Rush with any ferocity would now look in bad taste.
“I’ll never forget getting a phone call from Reverend [Jesse] Jackson,” Obama said. “He said to me, ‘You realize, Barack, the dynamics of this race have changed.’” Added Shomon, who was managing Obama’s campaign: “There was just no way to beat Bobby after his son was shot.”
But that was not the only misfortune to beset Obama’s congressional campaign.
Throughout Obama’s tenure as a state lawmaker, Shomon would stress nothing more vigorously to Obama than the importance of not missing votes in the General Assembly. This continual preaching from Shomon could irritate—and sometimes infuriate—Obama. On many of his three-hour commutes from Chicago to Springfield, an impatient Obama would phone Shomon and complain that he was making another pointless trip to the state capitol when it was clear that little would be accomplished in that particular session. Shomon would explain that it didn’t matter whether Obama’s presence made any difference to the capitol debate or to pending legislation, it was crucial to Obama’s future political career to have a high-percentage voting record so that a political opponent down the road could not accuse him of shirking his public duties. “You gotta show up for work,” Shomon told him. Obama, who loathed having his time wasted, balked and rebelled verbally—but he heeded Shomon’s advice and missed few votes during his time in Springfield.
There was, however, one instance in which Obama did not follow this plan—and it cost him dearly. As he did every holiday season, in December 1999 Obama gathered up Michelle and Malia, now eighteen months old, to visit his grandmother in Honolulu. These annual trips to his childhood home have served as a respite for the hardworking Obama, who looks forward all year to spending a couple of weeks decompressing in the serene tropical environment of his youth. But the 1999 trip was not stress-free, by any means. That holiday season, a showdown was brewing in the state capitol in Illinois. Governor George Ryan was pushing for reenactment of a gun control law known as the Safe Neighborhoods Act, and the General Assembly was locked in a heated debate over the bill. The legislation, among other things, would have raised the penalty for illegally transporting a firearm from a misdemeanor to a felony. Obama, a staunch gun control advocate who represented a district containing neighborhoods ravaged by gun violence, wholeheartedly supported the legislation. Opposition mostly came from rural conservatives, who argued that hunters and other law-abiding gun owners could be hit with felony counts for accidentally carrying a rifle or other firearm from place to place.
As Obama vacationed in the Pacific, the bill moved closer to a vote in a special session of the senate called the week between Christmas and New Year’s. Shomon jumped on the phone with Obama during that week, advising his boss that he ought to seriously consider returning to Illinois for a possible vote. Obama, however, had been spending a good deal of time away from Michelle and their young daughter in recent months, as he had two jobs—state senator and college law lecturer—in addition to campaigning. In fact, he had already truncated his usual two-week Hawaii trip to just five days because of his hectic campaign schedule. So at this point, leaving the family vacation early for the sake of work, especially during the holidays, would put him in a bad spot with Michelle. She was already displeased with her husband’s prolonged absences for the sake of his political career and, according to Obama, was barely on speaking terms with him. Moreover, Obama said, his daughter had come down with a bad cold, which worried Michelle. Obama was torn between his duty as a public official and his duty as a father and husband. In the end, he chose to remain in Hawaii.
Back in Illinois, Shomon was left to defuse a potential public relations bomb. The governor’s office and reporters were calling asking the whereabouts of Obama and if he could be counted on to vote should the bill come before the senate. Ryan, desperate for every vote, even offered to fly Obama from Chicago to Springfield. Shomon was in a no-win situation—and he stonewalled. For a day or two, he quit returning calls, hoping the issue would go away. How could he tell the governor and the media that his boss was on vacation in Hawaii as this important matter was debated? Shomon crossed his fingers that the bill would not come up for a vote. Unfortunately, that strategy failed, as no compromise was brokered in the waning hours. On December 29, the bill came to the floor and fell just three votes short of the thirty-six needed for passage. Obama was among three lawmakers Governor Ryan had relied on but who had missed the vote. “I’m angered, frankly, that the senate didn’t do a better job,” Ryan told reporters tersely.
As Obama’s plane touched down in Chicago the following week, he took another phone call from Shomon, who was not shy about letting him know of the political disaster awaiting him upon his return to Illinois. He warned Obama that this political ad was in his future: an image of Obama sipping a tropical drink on the Waikiki Beach while legislators fell just a few votes short of passing a tough anticrime bill, all of this transpiring as Chicago was suffering the highest murder rate in its history. Besides Governor Ryan, criticism came from various segments of the media. The Tribune, which, despite its conservative leanings, was a staunch advocate of strict gun laws, took Obama to task on its editorial page: “Sen. Barack Obama (D-Chicago), who has—had?—aspirations to be a member of Congress, chose a trip to Hawaii over public safety in Illinois.” Bobby Rush also piled on, telling the Tribune, “This vote was probably the most pivotal vote, one of the most important votes in memory before the General Assembly, and I just can’t see any excuse that Mr. Obama could use for missing this vote.”
It was during this episode that I first encountered Obama. About two weeks after the holidays, I was assigned a weekend reporting shift at the Tribune. And that Sunday afternoon, Obama assembled a group of senior citizens in his Hyde Park neighborhood to tout a proposal instituting price controls on prescription drugs. But with Obama’s missed vote still fresh in the public consciousness, reporters covering the event had little interest in the health care proposal and instead focused on seeking an explanation directly from Obama for the missed vote. Instead of fielding questions about health care, Obama found himself explaining how his daughter had become ill and how he felt duty-bound to stay with the family in Hawaii. He handled the questioning with a confident demeanor, but it was obvious that he felt chastened by the experience. Before a spread of news photographers and television cameras, he shifted from one leg to the other and maintained that he had put his family’s interests above his own political career. He cited his high-percentage voting record and said this occurrence was not the norm, but there were extenuating circumstances. “I cannot sacrifice the health or well-being of my daughter for politics,” Obama told reporters. “I had to make a decision based on what I felt was appropriate for my daughter and for my wife. . . . If the press takes my absence as the reason for the failure of the Safe Neighborhoods bill, then that’s how the press is going to report it. . . . I have the track record of someone in Springfield who takes his legislative duties seriously.”
Most of the roughly fifty seniors who listened to Obama seemed to buy his explanation of a sick child. When Obama maintained that the real culprit for the botched legislation was a feud between the governor and the senate president, many seniors nodded in support. I, however, was more cynical. Using the excuse of a sick toddler while vacationing in Hawaii seemed a bit hard to swallow. Thus, I began my story the next day in the Tribune this way: “Proving the political principle that one memorable public decision can define a politician for some time, state Sen. Barack Obama called reporters to a senior citizens’ home Sunday to unveil a health care proposal but soon found himself explaining his controversial Christmastime vacation.”
Rather than a rising star, Obama looked like a withering candidate. His performance reminded me of a comedian dying onstage.
The incident was indicative of Obama’s almost uncanny run of bad luck in the Rush contest. The missed vote, the questioning of his racial authenticity, the death of the incumbent’s son—Obama’s first major campaign in the public eye had become an utter disaster. Obama would later say that this period was one of the low points of his life. “Less than halfway into the campaign, I knew in my bones that I was going to lose,” Obama wrote in his book The Audacity of Hope. “Each morning I awoke with a vague sense of dread, realizing that I would have to spend the day smiling and shaking hands and pretending that everything was going according to plan.”
Over the next couple of months, Obama fared only slightly better. He managed to pick up the Tribune’s endorsement, after all. And he won a few high marks for his performance in public debates, although the major news media largely ignored them. The candidates’ only televised appearance, perhaps fittingly, went poorly for Obama. He resembled a fighter struggling on the ropes, desperately trying to prove he belonged in the ring in the first place. The rather informal panel discussion was hosted by Chicago’s public television station and featured a single moderator, Phil Ponce, asking questions of the candidates. By now, the three men had been rivals for some time, and the discourse tended to be combative. Obama and Rush’s other main challenger, Donne Trotter, accused Rush of failing to lead in Washington, and both argued that the district needed fresh, aggressive leadership. Rush, meanwhile, portrayed Obama as an overly ambitious young state lawmaker with modest accomplishments who had the gall to ask voters to send him to Washington. When Obama impatiently tried to interrupt Rush and plead his case, moderator Ponce cut him off and asked him to give Rush his time to speak—an unpleasant exchange that only furthered Obama’s growing image as a self-centered young upstart. To make matters worse, Rush batted away the interruption by averting his eyes from Obama and attacking Obama’s newcomer status: “Just what’s he done? I mean, what’s he done?” Obama responded by citing his history of organizing voters and poor residents, but Rush’s line cut through Obama’s message like a steak knife through butter. Obama’s candidacy was in tatters, and he lost the election by 30 percentage points.