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Rep. Chris Shays (search) has made campaign finance reform a priority during his tenure in Congress but now he faces a well-financed Democrat who is taking on Shays for his support of the war with Iraq.

Shays, a Republican who represents Connecticut's 4th Congressional District, is facing one of the toughest re-election challenges in his 17-year career, according to political analysts.

"This is probably Chris Shays' most difficult battle," said Nathan Gonzales, analyst for the Rothenberg Political Report. "I think this is a case of a strong challenger facing a strong incumbent."

Shays, one of the few moderate members of the Republican House who could find it detrimental to invoke the president's name too often while on the campaign trail, faces Westport First Selectwoman Diane Farrell (search) , who has raised an unexpected $721,000, mostly from individuals in the 4th District.

"His stridency on the war has disenfranchised a lot of the voters," Farrell told FOXNews.com. "People are unhappy. People feel he's changed."

While Shays, a member of the House Select Committee on Homeland Security, has been a strong proponent of the war, he says he does not feel his position has been entirely out of sync with his constituents, who range from the wealthy elite of Connecticut's coastal towns like Fairfield and Greenwich to the blue-collar service and factory workers of Bridgeport and Norwalk.

"Chris is very sensitive, he does listen to the constituents in the district; he has a conscience, and I think those are the things that make him a very special congressman," said Republican state Sen. Judy Freedman, who represents several towns in his district.

Shays Blasts Both Sides in 527 Flap

Talk of rampant 527 fund-raising groups harvesting tens of millions of dollars for attack advertisements in this year's presidential election has not made Shays (search) very happy.

As co-drafter of the House campaign finance reform bill, along with Rep. Marty Meehan, D-Mass., Shays was one of the chief proponents of taking "soft money," or unregulated and unlimited cash, out of federal party coffers. And in 2002, they were successful, as their bill was joined with Senate legislation penned by Sens. John McCain, R-Ariz, and Russ Feingold, D-Wis., and became law, signaling the most dramatic shift in federal election financing in decades.

But as their opponents had warned, the unlimited soft money squeezed out of the parties is now going to so-called "527" groups – independent political action groups that are impacted only marginally by the campaign finance law. Most of the 527s (search) that have emerged are pro-Democratic groups, according to the Center for Responsive Politics (search).

"It's an outrage," Shays said in a recent interview with FOXNews.com. "I'm seeing both sides conduct themselves in a way that is contrary to the spirit of the law."

Like McCain, Shays is blaming the bipartisan Federal Election Commission (search) for not clarifying the role of 527s when they interpreted the law into new rules last year. Unfortunately for Shays and others, the FEC said it won't consider restricting 527s until after the November election.

Shays said it's "ironic" that while Republicans generally opposed the reforms, the Democrats who supported them are benefiting most from the nearly $200 million in soft money raised through 527s this year.

So far, Shays himself has not been the target of a 527 ad campaign like the now-famous MoveOn.org ads against President Bush, or the Swift Boat Veterans for Truth (search) campaign questioning Democratic candidate John Kerry's Vietnam War service.

Soldier For, Maverick Against GOP

Depending on the topic, Shays has also been either a loyal soldier or a maverick within the GOP party structure. For example, he voted against impeaching President Bill Clinton in 1998. As vice chairman of the House Government Reform Committee, he spent many years battling the government over its handling of Gulf War illnesses (search) and the anthrax vaccines given to U.S. soldiers.

He is pro-choice and fiscally conservative. "He's one of our most independent members of Congress," said Chris Paulitz, National Republican Congressional Campaign (search) spokesman. "He embodies the 4th District."

But Farrell and her supporters say Shays has moved increasingly to the right over the years and his re-election ensures continued control of the House by conservative Republicans like House Majority Leader Tom DeLay (search), a lightning rod among liberals and moderates.

"I tell people a vote for Chris Shays is a vote for Tom DeLay," said Farrell, who is serving her second term as First Selectwoman, which is akin to a strong mayor or town manager. She counts Connecticut Democratic Sens. Joe Lieberman and Christopher Dodd among her supporters.

"In the past everyone said, ‘Shays is going to win.' Now they are saying, ‘Can Farrell win?'" said Walter Marcus, chairman of the Weston Democratic Party. "Clearly there is much more doubt (about Shays) than ever before."

Farrell says she can do better to help resolve some of the region's transportation issues, and has a finger on the pulse of what first responders in this area – much of the district is within an hour of New York City – need in the way of resources.

"I have had the good fortune to be here for the last seven years managing the town of Westport," she said. "I have the energy and I have the knowledge of what really needs to be done."

Martha Aason, chairwoman of the Westport Democratic Party, calls her "dynamic, thoughtful, experienced, conscientious. I couldn't say enough of Diane's qualifications."

But not everyone is charmed. "Diane has been one of the most charming and successful people in Westport, but she hasn't been a great administrator for Westport," said Pete Wolgast, chairman of the Westport Republican Party. He also accused Farrell of neglecting town duties while running for higher office.

"The fact is, she's lost it with me because she goes after Chris, trying to paint him as being in league with Tom DeLay … he's clearly not the same," said Wolgast.

Wolgast pointed to the work Shays has done on women's issues and the environment and on bringing home millions in transportation funding.

Shays said Farrell purposely misinterprets his record and wrongly paints him as a member of the "vast right-wing conspiracy," but is preparing for a tough contest nonetheless. Analysts say he is running a strong campaign and has raised over $1 million.

"Do I think I have a formidable opponent? Absolutely," he said. "If you are asking me if I keep two speeches in mind on election night, I always do."