11/03/2008 07:34 am ET Updated May 25, 2011

Bridgeport and Greenwich Could Thwart New England's Chance to Maintain Lone Republican Seat

Down the street from Sol Supermarket, across from Sandro's Rubber Company and J&H Auto Body, Mark Florentino sips coffee with five friends at New Colony Diner, in Bridgeport, Conn. The men, all over 70, are discussing the Southwestern Connecticut Congressional race between Republican incumbent Christopher Shays, who has served the House of Representatives since 1987, and his Democratic challenger, Jim Himes, a former executive for Goldman Sachs. The candidates are embattled in one of the closest races in the country.

"It's time for a change," says Florentino, who has voted for Shays in the past but this year will vote for Himes. Half the men nod in approval, but the others aren't sure. Shays, the only House Republican from New England, is well-liked in his state, even by Democrats, who appreciate his moderate views.

The men might not realize it, but their working-class city will likely have more to do with the outcome of the election than any other region in their district.

Bridgeport sits on the eastern-most fringe of District 4, 30 miles up the coast from Westchester County, N.Y. Once an industrial boomtown, Bridgeport is now mired in drug, education and unemployment problems. It is one of the few blue-collar enclaves in a Congressional district widely considered the richest in the country. Nicknamed the "Gold Coast," the region is home to lavish Wall Street bedroom communities like Greenwich, New Canaan and Darien. It houses a wide swath of moderate Republicans and Libertarian-minded Independents who are fiscally conservative and socially liberal. Residents here are generally against the war, but don't like government oversight. No Democratic has been elected to the House in District 4 since 1966.

But because of Bridgeport, that could change tomorrow.

With its heavy ranks of African-Americans, Hispanics and other minorities, the Democrat-leaning Bridgeport is now an epicenter of the Barack Obama movement. The city has witnessed a record-setting surge in voter registrations: since January, 9,068 new Democrats have signed up - 20 percent of total Democrats in the city. Only 625 new Republicans have registered during that time. Tomorrow, the new Bridgeport Democrats are expected to vote the party line, even if they have little concern for any politician not named Barack Obama.

Mike Brown, a 36-year-old barber and first-time voter, says he will select all the Democrats listed on the ballot. But when asked about the Congressional race, he responded, "To be honest with you, I don't even know who Himes is. I just like Obama. I'm not into politics."

Because of new voter registrations, "Bridgeport could hold the key to the whole Congressional election," says John Orman, a political scientist at Fairfield University.

For more than 20 years, Shays, 63, has embodied the District 4 ethos. One of the most moderate Republicans in Congress, Shays has reached across party lines and sponsored progressive bills promoting clean energy and the environment. He supports gay rights and women's rights. For his willingness to buck his party, he has picked up endorsements from New York City Mayor Michael Bloomberg, The New York Times and most of Connecticut's major newspapers.

Nevertheless, polls indicate that Shays is locked in a virtual dead-heat with Himes, 42, a fresh-faced newcomer from Greenwich, who served as vice president at Goldman Sachs before leaving the investment firm in 2002 to work on housing-development initiatives for a non-profit group in Hartford. With a campaign message of fixing the economy, he has raised nearly as much money as Shays and earned an Obama endorsement.

Republicans here are prepared for the worst.

"It's possible that this city could tip the scales," says Ward Thrasher, the campaign treasurer for State Senate Republican nominee Rob Russo.

Anti-War Sentiment Along the "Gold Coast"
Twenty-eight miles down Interstate 95 from Bridgeport, life is more comfortable in the town of Greenwich, home to one of the wealthiest communities in the world, populated by investment bankers and hedge-fund managers who make millions, if not billions. The town anchors a country-club corner of the state that contributed more than 40 percent of its federal taxes last year.

Like its wealthy coastal neighbors, Greenwich has been a GOP stronghold. But unlike party members in other sections of the country, Greenwich Republicans never fully embraced the Iraq war and its $10 billion-a-month price tag. Thanks in part to the foreign policies of the George W. Bush administration, the town has seen its number of registered Republicans shrink in the last decade from 15,573 to 13,604. In contrast, the number of Democrats has risen from 6,636 to 9,081.

That shift poses another threat to Shays, an early supporter of the war.

In 2004, Democratic Senate nominee and Greenwich native Ned Lamont was able to capitalize on the shift by running an effective anti-war campaign. He ousted incumbent Sen. Joe Lieberman in the Democratic primary but wasn't able to defeat him in the general election after Lieberman switched his party affiliation to Independent. Several Greenwich Republicans voted that year for Democratic presidential nominee John Kerry, and many more are expected to vote for Obama.

In an odd similarity, the race between Himes and Shays mimics the presidential contest; in each case, the older, non-traditional Republican is trying to fend off the younger, articulate Democrat with a long list of donors and a message of change. Like Obama, Himes has gained traction by linking his opponent to Bush, thereby pushing him to the right. Shays, in turn, tries to appear centrist by pointing to his maverick credentials.

"Shays is trying to say, 'I'm the John McCain of 2000,' but Himes is saying, 'No, you're the John McCain of 2008,' " says Orman.

In a coffee shop on Greenwich Avenue, just past the dressed-up windows of Brooks Brothers and Saks Fifth Avenue, investment banker Jim Chapman takes a break from thumbing his BlackBerry and making deals on his cell phone to rail against Himes.

"He's a pompous, arrogant phony," says Chapman, 46, who sits on the Board of Trustees for Chrysler. Chapman and Himes sent their children to the same prestigious private school before the candidate pulled his children out this year in favor of public school. Chapman views that move as a fruitless appeal to populism. "He's a former Goldman Sachs executive worth millions, and he's supposed to be a normal person? People will cut through the bullshit," he says.

A fiscal-hawk Republican, Chapman gravitates toward Independent-minded politicians and backed Joe Lieberman during his Democratic years in the Senate. He is a fierce supporter of Shays. "Chris is a pragmatic, cross-party politician," says Chapman.

But Himes has his own following of Greenwich investment bankers, many of whom have taken a hit during the economic crisis this fall. Anne Beaty lives in a large house on upscale Patterson Avenue. Her husband works in Manhattan's Financial District, and her two children attend Ivy League schools. Once a Republican, Beaty now displays a Himes sign in her lawn and wears a sparkling "Obama 2008" brooch on her dress.

"The parties have evolved," says Beaty, a video producer, in the foyer of her house, with her Labrador, JJ, lying on the plush red carpet beside her. "Shays is a perfectly charming individual, but he has voted wrong on the war all along."

For his part, Shays is trying to win voters like Beaty back, aligning himself with Obama in campaign ads and going as far as to suggest that the Democrat will win the presidency. "One thing I'll say about Chris Shays," says Orman: "Never count him out."

But because of trends running through Bridgeport and Greenwich, his time might finally be up.