In March of 2000, an ambitious Illinois state Senator didn’t need to see his latest fundraising report to know that his long-shot bid to oust an entrenched Chicago Congressman was on life support. But three weeks before the primary it was there in black and white: He had just $18,000 left in his campaign account and was $35,000 in debt.

Seven years later, as now-Sen. Barack Obama launches a presidential bid amid estimates that he will raise upward of $30 million in the first quarter of the year, the Illinois Democrat’s unsuccessful first Congressional campaign couldn’t appear more distant.

By most accounts, Obama was never able to fully gain his footing in his 2000 primary race against Rep. Bobby Rush. In his second book, “Audacity of Hope,” Obama wrote: “It was a race in which everything that could go wrong did go wrong, in which my own mistakes were compounded by tragedy and farce.”

But Obama’s close associates agree that the 31-point thrashing provided valuable lessons and set the course for his future political path.

“It came out very badly as far as the results are concerned, but it was a great learning experience for him,” said former Rep. Abner Mikva (D-Ill.), one of Obama’s political mentors and among those who encouraged his 2008 White House run.

Mikva said that while Obama knew that the race would be an uphill battle, it was the right time for him to try.

Getting In
Obama filed paperwork to run against Rush in early August 1999, less than six months after Rush had been trounced in his challenge to Chicago Mayor Richard Daley (D) in the February mayoral primary.

Rush’s poor showing against Daley — he garnered just 28 percent of the vote and even lost his home ward to the mayor — made the four-term Congressman look vulnerable.

Rush had risen to political prominence in the city as a leader of the Black Panther Party in the 1960s, and Daley’s ability to win 45 percent of the black vote in the primary had given rise to a belief that Rush’s loyal base was fractured.

As Obama soon would learn, that assessment turned out to be bogus.

The official kickoff for Obama’s campaign came on Labor Day 1999, the beginning of a seven-month sprint to the March 21 primary. A colleague of Obama’s in the Legislature, state Sen. Donne Trotter (D), also was running in the primary.

“We got in too late, we should have been in much earlier,” conceded Dan Shomon, a longtime Obama adviser who managed his 2000 race.

After all — this being Obama’s first real campaign — he was far from a household name and had never had to raise even the money to be competitive in a state Senate race, much less a Congressional contest. An early benchmark poll wasn’t promising, and the anecdotal evidence wasn’t much better.

Chris Sautter, Obama’s media consultant for the 2000 campaign, recalled walking around the South Side with Obama in October 1999. “Nobody knew who he was,” Sautter said.

Sautter was recommended to Obama by Chicago-based media consultant David Axelrod, who had a personal relationship with Obama but declined to work on his 2000 race. Axelrod is a top adviser to Daley, and his willingness to take on Obama as a client just months after the mayoral race would have appeared to be an act of retaliation against Rush.

However, Axelrod did serve as Obama’s top consultant for his 2004 Senate race, and he is playing a leading role in his presidential run.

Sautter also did the campaign’s direct mail after the original mail consultant Obama hired quit under pressure from the Democratic Congressional Campaign Committee, which supported the incumbent. By the end of 1999, Obama’s campaign had produced three mail pieces and done a month’s worth of radio ads.

But two events that fall and early winter cast a shadow over the campaign that was too large for any radio or mail messages to break through.

Tragedy and a Missed Vote
On Oct. 18, 1999, Rush’s son, Huey Rich, was gunned down on a South Side street. He died four days later at age 29, and news related to the tragedy saturated the Chicago airwaves for weeks.

Still grieving, Rush announced his run for another term on Nov. 1, 1999. A poll taken around the same time for Rush’s campaign showed the Congressman with 68 percent in the primary, compared to 10 percent for Trotter and 9 percent for Obama.

“There had been some negative feelings towards Congressman Rush because of the mayoral race,” Shomon said. “A lot of those went away when the public became very saddened and supportive of him when he lost his son.”

But Obama didn’t help his own cause when he missed an important vote on an anti-crime package during a special session of the Legislature in late December. Obama was in Hawaii for an annual visit to his grandmother during which his daughter became ill and was unable to fly. He chose to stay with her, and the package fell five votes short of passage.

Obama ardently defended his decision to remain with his family, but, politically, it gave Rush the upper hand.

“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,” Rush told the Chicago Tribune at the time.

Battle Over Credentials
Although the primary remained relatively cordial on its surface — none of the candidates ran campaign ads attacking the others — there were undercurrents that exposed socioeconomic and generational rifts between Obama and the constituency he sought to represent.

Obama, who first moved to Chicago as a community organizer in 1985, had first ruffled feathers among elders in Chicago’s black establishment during his 1996 state Senate race.

Then-state Sen. Alice Palmer (D) backed Obama as her successor when she announced she would vacate the seat to run in a 1995 special Congressional election. But after losing that contest she decided to run for re-election. She asked Obama to step aside, and he refused.

So when the 38-year-old Harvard-trained lawyer announced he would challenge the 53-year-old Congressman, many in the old guard had a wait-your-turn attitude.

They saw Obama as a young aggressor unschooled in the city’s machine politics trying to knock out a statesman of the black community — one who had earned his credentials on the street, not in an Ivy League classroom.

“Bobby Rush was a popular incumbent and who the hell was Barack Obama to run against him?” said Kitty Kurth, a Chicago-based Democratic consultant.

In a recent interview, Rush recalled he was surprised at Obama’s decision to run and said that it had been encouraged by “elitists in my district who were not satisfied because I represent the grass roots.”

Rush said that Obama’s Harvard credentials and gift for smooth talking — attributes that made him attractive to those who encouraged him to run — where no match for his history in the black community.

“I’m a fighter for my community and my community’s interests,” he said. “You had a style that came into collision with a legacy.”

Indeed, Obama’s Harvard law degree, coupled with the fact that he was not a native Chicagoan, ended up being among his biggest impediments. “This guy’s from Hawaii,” Trotter recalled the sentiment at the time. “He doesn’t know anything about 63rd Street.”

Trotter said Obama’s ethnicity — his mother is a white Kansan and his father is from Kenya — played little role in the 2000 race. He also said the idea that Obama was hurt because he was viewed as insufficiently black among district voters has been blown out of proportion.

Obama loyalists also point to his 2004 Senate primary win — where he captured the majority of the black vote — as evidence that the question of whether he is “black enough” to represent that community is null.

Rush’s 1st district seat has been held by a black Representative longer than any other Congressional district in the country. It includes some well-to-do white liberal enclaves, impoverished portions of the city’s South Side and working-class southwestern suburbs. The electorate is about 30 percent white.

Trotter and others familiar with Obama’s campaign said there wasn’t any doubt that Obama was more comfortable speaking to white audiences than to black audiences.

“He wasn’t talking the homeboy language, and there’s nothing wrong with that,” Trotter said. “There just was that comfort zone.”

Mikva, who was among Obama’s early supporters, said that the lessons Obama took away from the 2000 campaign were visible.

“The difference in how he used to speak in African-American churches before the Rush campaign and after the race was as different as night and day,” he said — adding that the changes were more in style than substance.

The Clinton Factor
While Obama sought to make the contest about the need for new leadership and tried to paint Rush as ineffective, the Congressman touted his seniority and his deep roots in the community, while suggesting that Obama had yet to sufficiently pay his dues in political service.

“My experience is African-American voters tend to be loyal, maybe more loyal than other voters, and they were certainly loyal to Bobby Rush,” Sautter said.

Not surprisingly, Rush garnered the backing of virtually all of Chicago’s machine establishment — save for Daley, who remained publicly neutral.

The Rev. Jesse Jackson, then-Cook County Board President John Stroger (D) and Sen. Dick Durbin (D), whom Rush had backed early in the 1996 open Senate race, all endorsed the incumbent, as did fellow Illinois Democratic Reps. Jesse Jackson Jr. and Danny Davis. Rep. Charlie Rangel (D-N.Y.) served on Rush’s finance committee.

But the biggest endorsement Rush got came from then-President Bill Clinton (D), who campaigned for him in Chicago and cut a 30-second radio spot. Rush was the first elected official in the state to endorse Clinton in the 1992 presidential election.

“Bobby Rush has been an active leader in the effort to keep guns away from kids and criminals long before his own family was the victim of senseless gun violence,” Clinton said in the ad.

Last week, Rush conceded that Clinton’s support in that race made it difficult to back Obama over Sen. Hillary Rodham Clinton (D-N.Y.) in the 2008 presidential contest. But home-state ties won him over.

“That campaign is over,” he said, referring to the 2000 primary. “I think that he would be an outstanding nominee for our party and an exceptional president.”

Although Rush and Obama have put away their differences now, the wounds left from the primary still were evident as recently as Obama’s 2004 race for Senate.

While the other two black Congressmen from Chicago served as co-chairmen of Obama’s campaign, Rush endorsed white millionaire Blair Hull in the primary. Despite spending more than $30 million, Hull’s candidacy eventually unraveled due to damaging allegations of spousal abuse.

Results Weren’t Pretty
While Daley remained publicly neutral in the 2000 race, many viewed the mayor as tacitly behind Obama.

Obama did have the backing of four ward organizations, including 17th ward Alderman Terry Peterson (D), one of the mayor’s top lieutenants. But in the end Obama never got close, garnering 30 percent of the vote to Rush’s 61 percent. “He never gave any reason for Bobby Rush’s black constituents to vote for him,” Mikva said.

Rush won huge vote tallies in the district’s 14 predominately black wards, including 74 percent in his home ward, which he had narrowly lost to Daley in 1999.

Obama got 64 percent of the suburban vote and his strongest showing was in the 19th ward, a white ethnic area on the city’s far southwest side, despite the fact that the head of the ward’s political machine worked against him. But the working-class neighborhoods were heavily populated by police officers and former police officers who embraced Obama in part out of their distaste for Rush and his Black Panther past.

Trotter recalled the unwritten message on the green and white signs in certain neighborhoods that promoted Obama and then-state Rep. Tom Dart (D), who was seeking re-election.

“If you were in that campaign you would have thought that his name was O’Bama,” he said. “There was too much of a space between the O and bama. You gotta love Chicago politics.”

Lessons Learned
Even with his resounding defeat, no one was writing off Obama’s political future.

“Sometimes you need to lose in order to learn how to win,” Rush said.

Trotter said that after the loss, Obama came back to the state Senate and began to build the type of legislative record he lacked in the 2000 race, which he would later use to build his 2004 statewide run.

“He’s a competitor,” he said. “By losing, I think it just made him want to try harder to achieve something down the road.”

Shomon said that most importantly, Obama used that first race to build the donor base that he would also rely on early in the 2004 contest.“What we also learned was that Barack had tremendous vote-getting power among white voters,” Shomon said. “It laid down his liberal progressive and African-American fundraising base.”

But Trotter recalls that perhaps it was Rush who learned the most important lesson from the contest — don’t take anything for granted.

“He remapped both of us out of the ward,” Trotter said, referring to the redrawing of district lines after the 2000 Census. “We both now live in the honorable Jesse Jackson’s Congressional district.”