updated 3/8/2007 3:28:42 PM ET 2007-03-08T20:28:42

Most state leaders would consider Illinois’ Democratic powerbrokers lucky to have two homegrown presidential candidates vying for the top of their party’s ticket.

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Now comes the hard part—choosing whether to back rising political star and local hero Barack Obama, or whether to get behind a trusted ally and political veteran with strong ties to the state, Hillary Rodham Clinton.

Obama and Clinton are heavily courting Prairie State insiders who can deliver money and votes for their presidential campaigns, especially in Chicago—one of a half dozen of the nation’s top locales for raising political money.

“A lot of people are having a real hard time trying to decide,” said Kevin O’Keefe, a Chicago attorney who has known Clinton for decades. “They love their homestate senator, but they know Senator Clinton has been around longer.”

An Illiniois senator, Obama was raised in Hawaii, but settled in Chicago after college and worked as a community organizer. He left to get a law degree from Harvard, but returned to practice civil rights law and launch a political career.

Clinton, now a New York senator, grew up in the Chicago suburb of Park Ridge, a largely Republican enclave where she was a Goldwater Girl. But her exposure to progressive politics goes back at least to her teens, when she attended a speech by Martin Luther King Jr. in Chicago. Her husband, Bill Clinton, was nominated for a second presidential term at Democrats’ 1996 convention in the Windy City.

Both candidates are exploiting their local ties as fully as possible.

Obama, Clinton and other 2008 contenders face huge pressure to prove their viability by raising money quickly. Political analysts estimate the candidates will have to raise $100 million each this year to be competitive in next year’s primaries and caucuses. That requires the aid of supporters with networks of friends and associates willing to make donations.

‘A desire, an intent’
Many of the state’s top Democratic officials and fundraisers had been expected to back Clinton, but Obama’s entry into the race changed that.

Mike Bauer, for example, decided to use his years of fundraising experience and contacts in Chicago’s gay community to raise money for Obama. He helped with Obama’s first fundraiser after the campaign’s official launch last month—a huge Chicago event that Bauer says was intended to make a statement.

“Clearly there was a desire, an intent, by the Obama campaign to hit the ground first in Barack’s hometown,” he said. “It was important, both for financial reasons and psychological reasons, to show that he has tremendous support from the people who know him the best.”

Bauer said he knows several of the presidential candidates and decided to help Obama after a personal request from the senator. Obama contacted him around Thanksgiving to discuss a possible run for president and seek Bauer’s support if he did run.

O’Keefe, however, praises Obama, but plans to back Clinton. That means she’ll have all the fundraising connections and political wisdom O’Keefe gained by putting together Bill Clinton’s 1992 campaign in Illinois and working in the Clinton White House.

On the other hand, Chicago Mayor Richard Daley, a longtime Bill Clinton ally, has endorsed Obama. Illinois House Speaker Michael Madigan, despite occasional digs at Obama in the past, has proposed moving up the Illinois primary to give him a big early victory.

‘He’s hiding under his desk’
U.S. Rep. Rahm Emanuel, however, is conspicuously avoiding any public comment on whether he’ll stick by his plans, announced before Obama was considering a run, to back Clinton.

“He’s hiding under his desk,” Emanuel’s spokeswoman, Kathleen Connery, joked.

He would be a valuable asset for any campaign. Emanuel was one of Bill Clinton’s key campaign strategists and is regarded as one of the country’s sharpest political minds. Plenty of people around the country owe him favors for his key role last year in Democrats winning control of the U.S. House.

Of course, Obama and Clinton aren’t the only players in the Illinois fundraising game. Former North Carolina Sen. John Edwards, for one, is trying to take advantage of his years as a trial lawyer by courting the state’s legal community.

Despite past support of Obama, prominent Bloomington lawyer David Dorris is enthusiastically supporting Edwards. Dorris said he got a friendly call from Obama after a newspaper story mentioned he was an Edwards backer.

“He said, ‘Dave, you underestimate me.’ I said, ‘No, I don’t, Barack. The problem is, you underestimate the difficulty of what’s waiting for you.’ “

While Clinton is trying to mine political contributions in Chicago, Obama and other candidates aren’t about to give her a free pass on New York.

New York attorney Jeh Johnson, for example, a top Air Force official under Bill Clinton and an adviser to the Kerry presidential campaign, had decided to stay on the sidelines of the 2008 campaign until Obama emerged as a potential candidate.

“Of course, I have reservations and misgivings about not being with the Clintons in 2008,” Johnson said. “I don’t think Senator Clinton would be a bad president, but Barack is somebody who I find particularly appealing.”

© 2013 The Associated Press. All rights reserved. This material may not be published, broadcast, rewritten or redistributed.

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