GREENWICH, Conn. — Just before noon on a gloomy, gray day last week, Speaker Dennis Hastert (R-Ill.) joined the most outspoken leadership critic in the GOP Conference at a yacht club here and respectfully agreed to disagree.

The occasion was a $1,000-a-plate luncheon for 4th district Rep. Christopher Shays, a vocal, occasionally quirky moderate who perennially appears on Democratic target lists. Hastert accepted Shays’ invitation to join him and about 90 affluent donors at the Belle Haven Club despite the fact that Shays regularly makes the Speaker’s life difficult.

“It is not easy to be Speaker of the House, and there will be some of you who say, ‘And you don’t make his job any easier,’” Shays said in his introduction of Hastert, drawing knowing laughter from the audience. “I wanted to say that before he did.”

But Hastert said nothing of the sort, despite the fact that Shays often withholds his support for key party-backed bills such as the Medicare prescription drug measure and the annual budget.

Most notably, Shays is the only GOP lawmaker who has called on Majority Leader Tom DeLay (R-Texas) to relinquish his title amid ethical troubles. And when Republicans pushed through a controversial set of ethics rules changes in January, Shays called the move “stupid” and symptomatic of a lack of ideological diversity at the leadership table, even though the decision to change the rules was essentially made by his friend Hastert alone.

None of those issues were on the agenda last Wednesday, when residents of one of the nation’s wealthiest Congressional districts gathered on a deck overlooking Long Island Sound to eat chicken and hear a few words from the Speaker.

“Chris is a person who sometimes leads with his heart, and he should,” Hastert said. “I don’t always agree with Chris, but he’s part of our system. He’s part of our team.”

Shays had earlier catalogued all of the senior committee positions he holds, and Hastert picked up that theme. “Chris deserves to be a leader on a lot of those committees that he’s on because he understands them,” he said.

Of course, the Hastert-led Republican Steering Committee has frustrated Shays’ gavel ambitions in the past.

In 2003, Shays was passed over for the Government Reform Committee chairmanship despite his active campaigning for it and the fact that the winner of the post, Rep. Tom Davis (R-Va.), was less senior than Shays.

And earlier this year, Shays was booted off the Budget Committee, a panel on which he had served as vice chairman and where he had hoped to one day become chairman.

‘An Olive Branch’

Hastert began with his usual stump speech, comparing his current job with his previous experience as a teacher, coach and school bus driver.

Hastert said one of his chief duties was seeking “consensus” from his Members.

“I don’t like to use the word compromise, people think you’re soft and squishy,” Hastert said, drawing laughter as he gestured toward Shays. “That’s all right, Chris.”

Hastert then went into an extended riff on economic matters, and the GOP’s record on bankruptcy, class-action reform and other business issues.

The message was well-suited to the audience, since in his own remarks Shays called the financial services industry “the machine that has made our district so important to the rest of the country” and many of the attendees made their fortunes on Wall Street.

Hastert steered clear of discussing social issues such as stem-cell research, an area on which many Greenwich residents would disagree with the national Republican leadership, despite their affinity with the party on other topics.

At a pre-luncheon photo reception inside the elegant, mariner-themed club, Greenwich First Selectman Jim Lash said, “This is one of the few sections of Connecticut that voted for [President Bush in 2004], so the climate in Greenwich is good.”

Lash, the town’s top elected official, described it as economically conservative but “very divided” on social issues like abortion.

As for the day’s featured guest, Lash said, “I don’t think there are strong feelings here about Mr. Hastert. I think people separate him as a person from the positions of the Republican leadership.”

Lash said that opinions among the town’s Republicans of DeLay were “very split. Nobody is neutral about Tom DeLay.”

After a brief chat with Hastert at the reception, Jay Walker, chairman of Walker Digital Laboratories who is best known as the founder of priceline.com, said he had met Hastert before and always found him open to hearing new ideas.

“I think the Speaker is broad in that he is always talking to the different constituencies,” Walker said.

Shays’ donors are aware that he needs electoral help. In 2004 he beat Westport First Selectwoman Diane Farrell (D) 52 percent to 48 percent, and Farrell is now weighing whether to run again.

Eunice Hanson, who helped organize for the Shays campaign in Easton in 2004, said she thought next year’s election might be even tougher.

“There are a lot of Democrats [in this district] and they think they should own it,” she said. “They’re better organized this time.”

In addition to being moderate Republicans in the Shays mold, Hanson and her husband, Lee, have a more personal reason to admire their Congressman. On Sept. 11, 2001, their son, daughter-in-law and two-year-old granddaughter were on United Airlines flight 175 from Boston, which crashed into the World Trade Center.

Lee Hanson said that in the aftermath of the tragedy Shays had been a “huge help,” talking with them on the phone and frequently relaying updated information to them and other victims’ families.

While the Hansons have a personal reason to back Shays, other Republicans at Wednesday’s fundraiser had more strategic political concerns.

Jennifer Stockman, national co-chairwoman of the group Republican Majority for Choice, said she had been a longtime Shays ally, helping to raise money for him and other like-minded GOP moderates.

In addition to showing her support for Shays, Stockman also had some business to conduct. Before the luncheon began she approached Hastert in hopes of securing his support for a bill that would provide emergency contraception for rape victims.

Stockman said Hastert told her he would “take a very close look at it.” She described the measure as one the mostly conservative GOP leadership could use to reach out to centrists.

Moderates “need an olive branch from the Republican Party,” Stockman said.

‘Chris Is a Target’

The neighborhood of Belle Haven is perhaps best-known as the site of the infamous 1975 murder of 15-year-old Martha Moxley, a crime for which Kennedy cousin Michael Skakel was later convicted.

Following the frenzy that surrounded that case, Belle Haven instituted very strict laws about what the media could and couldn’t do in the private community.

Because of those restrictions, Hastert and Shays couldn’t hold a press conference at the yacht club, so instead Hastert’s small motorcade sped over to a waiting group of local reporters at the Greenwich Town Hall following the luncheon.

Aside from some regional issues such as the possible closing of the submarine base in Groton, the questions mostly focused on Shays’ electoral prospects and the controversy surrounding DeLay.

Hastert said he had come to help Shays because “Chris is a target” and “people in this district and in this area need to understand that we support Chris.”

Hastert was asked about Shays’ calls for DeLay to step down, and the Speaker reiterated his support for his fellow leader.

“Until he is actually brought up before the ethics committee and actually accused of something, I’ll support him,” Hastert said.

Shays, meanwhile, criticized Farrell for the tone of her 2004 campaign and acknowledged that his unwillingness to go negative on his opponents in the past had made winning more difficult.

“I’ve never run against someone, and that may have made my race a little closer,” he said.

National Democrats and their aligned groups have already begun trying to lay the groundwork for a Shays’ loss in 2006, sending automated telephone calls into the 4th district on Social Security and a variety of other issues.

Shays said at the press conference that he had already received several automated calls at his home “telling me to call myself.”

‘Playing Offense’

Hastert’s trip to Greenwich was just one brief stop on a typically packed recess travel schedule. The Speaker had already visited two districts in Pennsylvania that week and was set to fly to Vermont and Boston for more Republican gatherings.

Following the press conference, Hastert slipped into a back room at the town hall for a brief interview, during which he extolled the benefits for the GOP of expanding the electoral playing field to places like New England.

“I’m an old coach,” Hastert said. “If you’re not playing offense, you’re probably not playing ball.”

While the 2006 election remains 17 months away, Hastert said that these early campaign swings would pay future dividends.

“The way I view it is an ounce of prevention is worth a pound of cure, and if we’re out there early, especially in districts that could be targeted, and helping these people get some momentum early on, it’s a lot better than trying to do it a month before the election,” Hastert said.

During his luncheon speech, Hastert said that he used his trips home to his Illinois farm as an opportunity to relax and think without all the distractions of modern life.

“I don’t have a cell phone,” he said. “I don’t have one of those pagers … blueberries, blackberries, whatever they are. I don’t wear those.”

But his frequent road trips provide less time for introspection, and Hastert said that he had visited about 200 districts per cycle in the past four years. In April, Hastert spent several days in the hospital after suffering from kidney stones.

Despite the health scare, Hastert hasn’t cut back on his travel and has made only minor changes to his lifestyle.

“I haven’t changed my style. I’ve probably changed my diet a little bit. I drink more water and less of anything else,” Hastert said, adding that he has cut back on coffee. “I’ve always been pretty disciplined. I don’t drink a lot of pop.”

While the schedule is grueling, the 63-year-old Speaker says the constant travel doesn’t tire him out.

On the contrary, Hastert said, “I think you build up a head of steam doing this.”