His first foray into Fairfield politics wasn't all that successful. Kenneth Flatto, who officially stepped down as first selectman Tuesday after serving in the post 12 of the last 14 years, first ran for local political office in 1993 as a candidate for a seat on the Representative Town Meeting.

He lost.

"It was myself, Salina Strong and Fred Miller," Flatto recalled during a recent interview in his Sullivan-Independence Hall office with not only a reporter and photographer, but two Girl Scouts on hand as part of the annual "Scouts in Government" program. "The Democrats only ran three candidates. The Republicans ran five, including, I think Penny Hug." (He later went on to defeat Hug for first selectman in 2003.)

Those five candidates in the district included, for the first time, three Fairfield University students. "We lost partly because the students at Fairfield U. got about 400 student votes," Flatto said. "They were pretty aggressive."

Despite the outcome, Flatto, now 58, said he enjoyed running for office. "I worked hard going door-to-door and I took a liking to it."

Newcomer to Fairfield, but not to politics

But he wasn't exactly a newcomer to politics. While living in New York City, Flatto was a Democratic district leader from 1985 to 1989.

"We were in the Gramercy Park/Stuyvesant district," Flatto said. "I was kind of a community leader and had been active in politics as a neighborhood leader in Gramercy Park/Union Square. I founded a community group, the Union Square Community Coalition, in an effort to clean up Union Square Park. It was a dive, a real mess."

Flatto and his wife, Liz, moved out of the city to Westchester. There, he was working as the deputy commissioner of finance for city of Yonkers, and doing financial consulting on the side. But they'd been visiting Fairfield for about five years.

"Friends of my wife's from college lived here," Flatto said. "We were visiting on a regular basis and took a liking to the community. I vividly remember one thing we noticed and really liked was the friendliness of the merchants."

In the fall of 1990, they pulled up stakes in Westchester and headed east to Fairfield.

Before testing his own fortunes as a candidate in Fairfield, Flatto worked on Jim Fox's campaign for first selectman in 1991. During his unsuccessful run for the RTM in 1993, he also was active in Christine Neidermeier's first selectman campaign.

Ice rink furor fuels political fortunes

In 1995, then-First Selectman Paul Audley, a Republican, was under fire for his support of a municipal skating rink, that was to be built and managed by a private developer on town property behind the Carolton Convalescent Hospital.

"I think the biggest thing was the big community issue -- the skating rink saga," Flatto said. "The neighbors got very upset." Some, like Flatto, thought the property would be needed to build a second high school in town.

"I think I was the first to come out against it," he recalled. "I made it one of my platform issues" as he launched his own campaign for first selectman.

Some of his first supporters, he said, were from the Mill Plain Road area nearby the rink site -- and they were not all Democrats.

"Truth was, I honestly did not expect to win that election," Flatto said. "I was a very new face to the community. I knew it was an uphill battle."

But, he thought, it would be a great learning experience, although at the time he was more interested in running for the Board of Finance. But Democrats were having trouble finding a candidate to challenge Audley for the top job, so Flatto got the nod.

"Toward the end of the campaign I started to believe I had a chance because of the controversy of the skating rink," he said, adding, however, that he felt he was "very much on his own" with many of the active members of the party getting older. "They'd `been there, done that,' " he said.

He didn't win, but did garner enough votes for a seat on the Board of Selectmen.

But two years later, when Audley decided not to seek re-election, Flatto ran for first selectman and defeated the GOP standard-bearer, Jack McCarthy.

Comeuppance: `I was a little hurt'

But Flatto's tenure in the top job was short-lived. Two years later, he was challenged by veteran state Rep. John Metsopoulos -- and lost.

"I was shocked when I lost to Metsopolous in 1999," Flatto said. "I thought by the end of my first term I really had grown into the job. It did take six to nine months to feel like I really had a good grasp on it. I felt very comfortable with the budget process." The hardest part, he said, was "getting to know all the players."

That election, according to Flatto, marked a turning point in local campaigns, at least as far as fundraising went. "The last two weeks, Mr. Metsopolous spent almost $50,000" he said. "He raised about $80,000. It was a record for a first selectman's race here."

Flatto was able to hold onto a seat the Board of Selectmen, but in the minority. "It was very hard the first few weeks," he said. "It took about two to four weeks to sink in. I was a little hurt."

Though not excited about being returned to simply a selectman, Flatto decided he would serve nonetheless. "I didn't feel it would be fair to the public to walk away," he said. "I really tried to serve honorably."

At that point, he figured he'd tried his hand at a political career and that was the end of it. He wasn't inclined to run again.

"But as Mr. Metsopolous governed, he seemed to run into more and more problems and arguments with people," Flatto said, and once again he started to think seriously about making another run for the first selectman's job. "By January of 2001, I realized the opportunity that I had, with Mr. Metsopolous struggling a bit. If I wanted to run again, I believed I had a good chance."

`Comeback kid'

There was, however, some indecision within the party and Flatto faced off in a Democratic caucus with another potential first selectman candidate, Anthony Janotta. "I ended up getting about 40 percent of the vote, but it was not easy going back to the party and saying, `I want to be the comeback kid.' "

But he did come back and won the rematch with Metsopoulos -- and continued winning fairly easily in three subsequent elections for the town's top job.

But Flatto's interest appeared to drift to the state political stage over the last year or so, particularly last summer when he made a brief, unsuccessful bid for the Democratic nomination for state comptroller. By early March, he was still refusing to publicly state his intentions regarding re-election this year, a decision that became moot March 22 when Gov. Dannel Malloy announced that he planned to appoint Flatto as his director of special revenue, an office that oversees the state lottery and legalized gambling at the Indian-run casinos.

Fairfield Metro: Pride and panned

Flatto stepped down as first selectman several months before the town's third train station -- Fairfield Metro, off lower Black Rock Turnpike -- is scheduled to open.

The project, initially proposed as part of a sprawling, multi-faceted commercial development, has been in the works for more than a decade. Launched during the administration of his predecessor, Metsopolous, and tweaked by Flatto when he returned as first selectman, it remains one of his proudest accomplishments.

But it also became a lightning rod for controversy, unleashing the harshest and most enduring criticism of Flatto during his tenure. Much of the heat ignited it when Flatto removed environmental oversight of the project from the Conservation Department staff, prompting the Conservation Commission to assign the job to a consultant.

"I honestly believe this is a case where I wouldn't have done it any differently," Flatto said. "The surprise was when the permitting process took place and it got delayed. I worked for a year and a half behind the scenes to try and fix and help the permitting process; to try and do it without an argument. To try and get the Conservation Department to agree to the terms of the permit that the commission approved."

Flatto argued that he had to remove Conservation Director Thomas Steinke and his staff from their usual oversight role because they had caused numerous delays with the project, causing the private developer in the Fairfield Metro partnership, Blackrock Realty, to threaten a lawsuit. That action, however, triggered a series of lawsuits by a local citizens' group against Flatto and the town, all of which have yet to be resolved.

Blackrock Realty officials contended Steinke was changing the requirements of the approved permit. The staff felt "they were defining the permit," Flatto said.

"Blackrock Realty and the town managers all believed the staff was making decisions beyond what the commission approved," Flatto said, so he decided to step in and yank Steinke and his staff from their oversight. Town Attorney "Dick Saxl and I said, `Enough is enough,'' he said.

Still, Flatto said, "it was one of two or three of the most difficult decisions I had to make. I did not want to take staff off the project. It was a last resort."

Alexis Harrison, a member of the "Concerned Citizens" group that field the lawsuits and a Republican RTM member, said they believe Flatto encouraged the developer to start demolition on the site before conservation permit conditions had been met.

"Ken can do much to restore his reputation in the handling of the FMC project if he would finally revoke his ill-advised December 2007 letter to the conservation director, and restore the Conservation Department back to proper oversight," she said.

Flatto, however, stands by the action. "It was a good solution," he insisted.

With the delays and the economic collapse, Blackrock Realty went into foreclosure and its share of the project has yet to come to fruition, though it has since restructured its financing. But with aid from the state -- the third party in the Fairfield Metro agreement -- work on the train station, commuter parking lot and infrastructure to the site is nearing completion and is expected to open this fall.

Pension plans -- and reputation -- take a hit

In December 2008, the news that financial investment wizard Bernard Madoff was, in reality, a huge rip-off artist left town officials reeling. Fairfield's joint pension board had for years been investing with Madoff's fund-- a Ponzi scheme that collapsed, causing worldwide losses in the billions -- through a so-called feeder fund. They thought the market value of their investment was $42 million. Overnight, that sum became zero.

Many criticized Flatto, who as first selectman, served on the Town Employees Pension Board and on the joint board. It is the joint board that makes the investment decisions, with the advice of a consulting firm.

"The most frustrating part is I wasn't here when the town decided to invest with the Madoff feeder funds," he said. "The leaders of the pension boards were all active Republicans and had huge amounts of investment experience."

Flatto, however, suffered similar criticism over the investment losses since he is a CPA, and had promoted his financial management expertise in his political campaigns.

The town's pension consultant, he said, had been the biggest advocate for investing into what was then known at the time as the Tremont Broadmarket Fund. "From 1995-08, except for '01, the stock market went up," he said, but even then Broadmarket was not one of the town's best-performing funds.

"There were three others that did better. So it did not raise any red flags. Some of our funds were averaging 15 percent, and Tremont Broadmarket was 10 percent. No one every said anything for eight years."

He said, again "behind the scenes," that for the last four or five years prior to the Madoff scandal, he raised questions about the consultant. "I felt that the consultant was not doing their job that well, and they were not giving us enough fund advice, it was more marketing," Flatto said. "I wish I had tried to change the consultant earlier."

The town has filed suit against Madoff, his family and others involved in the Ponzi scheme. It also dropped the pension consultant, hired a new one and has recouped some of the money, through investments, that it had lost.

"As I leave office, the town is very aggressively going after many of the players and we are making huge strides," Flatto said, "and having very positive progress in our lawsuit." He believes that before long the town will recover what he termed "a significant asset" for the pension fund.

Keeping `enemies' close?

Two key appointments Flatto made to his administration were the town's fiscal office and human resources director.

Both jobs went to Republicans who, at some point, had sought to run against Flatto -- Fiscal Officer Paul Hiller and Human Resources Director Mary Carroll Mirylees.

"That was definitely a coincidence," Flatto said. "It was not by design."

During his first term in office, Hiller was on the Board of Finance. "He was always very gracious to me, and a savvy and bright individual," Flatto said. After Hiller lost a GOP primary for the first selectman nomination, "I realized he was on the outs, so to speak, and the party was divided."

Hiller was one of three people interviewed when longtime town Fiscal Officer John Leahy retired. "Paul had the most civic experience and the most business experience," Flatto said. "He went to Wharton; he had great credentials."

Later, when Holly Francis left the HR department, Flatto said someone -- he doesn't remember who -- suggested Mirylees because she a background in administration and personnel.

"We needed to find somebody fast," he said. "It wasn't like I was looking for people who had run against me."

Flatto said the two appointments simply reflect his style. "I work with everybody," he said. "I work with every official. I work in a very fair and positive way, no matter who agrees with me. That's why I ended up a very popular first selectman and won so many elections."

A `different, creative thinker'

Flatto considers himself a "significantly different, creative thinker in coming up with ideas," establishing task forces and commissions to devise new programs and approaches.

John J. Sullivan, the legendary Democrat who held the first selectman's job a record 24 years, from 1959-83, "has a legacy of open space," Flatto said, "but people brought the projects to him and he carried out the ideas of other people.

"I had to lead," he said.

Flatto said he's proud of the open space property the town acquired during his tenure. "Over 100 acres and 13 properties from Hoydens Lane to Lower Wharf to Whitewood Knoll," he recounted.

Next to open space acquisition and the Fairfield Metro rail station, Flatto is proud of the public building projects undertaken on his watch -- the expansion and renovation of the Fairfield Public Library's main branch, opening two high schools, building and renovating several other schools, Ludlowe Middle School among them. "No major roadblocks, no referendums," Flatto said. "The building committees were great."

"I feel very good about the array of projects I helped with, the broadest array of any first selectman, except for John Sullivan," he said.

`I'll still be around'

Now that his time as Fairfield's first selectman is history, Flatto says his role in town has changed, but is not over.

"I'll still be around," he said, participating in civic affairs as a citizen, not an elected official.