Washington – It’s a good bet the many pups he’s rescued are no more dogged than Mark Greenberg in his pursuit of a seat in Congress.

In his long-running campaign to win the 5^th District seat currently held by Democratic Rep. Elizabeth Esty, Greenberg has positioned himself as a Republican Party outsider and has tried to distinguish himself from Republican rivals by insisting he is the true conservative in the race.

It’s a strategy that failed twice, but one the candidate is willing to try again.

One observer says Greenberg has a few things in his favor this year, including “a drag at the top of the ticket,” a reference to Democratic Gov. Dannel Malloy, whose failing popularity may dampen Democratic turnout. Mid-term elections, when there is no presidential contest to electrify voters, have lower turnouts to begin with.

“There will be an older, whiter electorate and I think that will help Greenberg,” says Gary Rose, head of the political science department at Sacred Heart University.

Greenberg’s campaign declined to cooperate with The Mirror for this profile, but his apparent strategy is to portray himself as an accomplished and experienced businessman, job creator, community leader and family man.

Greenberg, 60, owns millions of dollars worth of real estate and amassed a fortune as a landlord. MGRE LLC., the company he founded, is “one of the largest real estate management firms in the Northeast,” his website says. His real estate investment and development work has created “hundreds of jobs for the construction trades” and elsewhere, it says.

Greenberg and his wife, Linda, have five young children and live in Litchfield. His campaign website proclaims he is “Proven, Experienced. Accountable.”

The Republican challenger says his years of trying for the congressional seat have made him a better campaigner with a seasoned campaign staff.

He is running as an unflinching conservative who supports tax cuts and smaller government—with the exception of an increase in defense spending. He opposes the Affordable Care Act as a “failed, big-government experiment” that is “costing millions of people their health care coverage as well as their jobs.”

He opposes abortion, except in cases of rape, incest or a danger to the life of the mother; and considers gun ownership a right.

So far in his latest campaign for Congress, however, Greenberg has moderated some of his more strident positions and avoided making statements about privatizing Social Security or raising the retirement age, suggestions he made previously when running for the GOP nomination.

Nevertheless, Esty and her Democratic Party supporters are trying to portray Greenberg as an extremist who appeals to the tea party segment of the GOP and is out of step with Connecticut voters.

Some Greenberg supporters do identify themselves with the tea party, including Peter Schiff, an investment broker, author and financial commentator who ran as a Republican for the Senate in 2010, but lost a GOP primary to Linda McMahon.

Schiff is a proponent of cutting all government spending, including popular programs like Medicare and Social Security. He said the notion that a Connecticut Republican must be moderate to win an election is a myth.

“To me a moderate Republican is basically a Republican who is really a Democrat,” he said. “Generally when people have a choice between two Democrats, people pick the true Democrat.”

Schiff said he met Greenberg at a 2010 Republican Town Committee meeting.

“I listened to his speech and thought ‘Wow, he’s really good,’” Schiff said. “I think he’s genuine. I don’t think he’s running or office because he’s on a power trip.”

Michael Barnes, a contributor to Greenberg’s campaign who belongs to the tea party and is an executive of an engineering firm in Brookfield, said he agreed with Greenberg on most issues, especially fiscal policy. Greenberg “understands why (government) bailouts don’t work,” he said. Barnes also said he believed Greenberg leaned toward libertarianism on some social issues.

He said Greenberg would vote his conscience in Congress, and not just “go along with party leadership.”

Greenberg has also won the support of Tim Slocum, the mayor of Cheshire, Esty’s hometown, who also identifies with the tea party.

“I don’t agree with every positon he takes on every matter, but I do respect him,” said Slocum, who has endorsed Greenberg.

As for Esty, who Slocum sees frequently in Cheshire, she is a “nice person” and “well meaning,” the mayor said.

“We’re always polite to each other other but I don’t think her agenda is Connecticut-specific,” Slocum said.

Outsider becomes GOP insider

In 2010, Greenberg finished a close third in a three-way Republican primary in which he spent more than $1 million of his own money. Two years later he lost a GOP primary for the 5^th District seat again.

But Greenberg won his party’s nomination this time, and the backing of the national Republican Party. The National Republican Congressional Committee has named Greenberg a “Young Gun,” a designation given to GOP challengers who are thought to have the best chance of knocking off a Democratic incumbent.

Yet The Hill, a Capitol Hill newspaper, said the promotion of Greenberg and three other Republican candidates to “Young Gun” status did not change their long-shot status. The Hill said all four hit their fundraising goals – it likely helped that Greenberg is willing to self-fund his campaign — but are running in blue-leaning districts that Republicans haven’t been able to win in for some time.

Although the 5^th District has grown in the number of Democratic voters, it was created in 2002 by a bipartisan commission as a swing district and has had GOP representation in the past.

But those Republicans were moderates, like former Rep. Nancy Johnson. So was Andrew Roraback, the Republican who ran against Esty two years ago and nearly beat her, though the swell of Democratic support for President Obama’s re-election held him back.

“Greenberg wasn’t the candidate most Republican strategists were hoping would win the nomination — he’s farther to the right than Andrew Roraback was in 2012,” said David Wasserman of the Cook Political Report. “But it’s a tough year for Democrats, and it could be close.”

The recent entrance of John Pistone, who is running as an “unaffiliated conservative” in the race and tacks even more to the right of Greenberg “could make Greenberg look a little more like a centrist” and help him with independent voters, Rose said. But Pistone might siphon off some of the most conservative voters in the 5^th District, the political science professor said.

A soft spot for dogs

Although he might come off as a hard-nosed businessman, Greenberg has a soft spot for stray dogs and cats.

He and his wife established the Simon Foundation, an animal shelter in Bloomfield, after years of personally adopting stray dogs and cats they found on the street.

Gordon Willard, executive director of the Connecticut Humane Society, said Greenberg’s 36,000 square ft. facility cost millions of dollars and, for that reason, is unique in the state as a private pet adoption center.

There are tax write offs for charitable ventures, but Willard says that’s not likely to be Greenberg’s sole motivation.

“Animals are being helped,” he said. “Anyone who does that is a good guy.”

But Greenberg also has a combative side.

He’s recently sparked a dustup with the Democratic Congressional Campaign Committee, that is helping Esty in her effort to keep her seat. At issue is a 99-page “Mark Greenberg Research Book” compiled by the DCCC, similar to other documents the group has created on other GOP candidates. The research book says Greenberg’s real estate company has been sued 58 times, a phenomenon the Greenberg campaign said is normal in the real estate business.

The research book detailed Greenberg’s vast property holdings and his position on dozens of issues.

But what set the candidate off is the book’s statement that “’Greenberg identifies as Jewish.” Greenberg interpreted that as a personal assault on his religion, even though the head of the DCCC, Rep. Steve Israel, D-N.Y., is also Jewish.

The Greenberg campaign released a You Tube video this week attacking the document, calling it “99 pages of hate.”

Business lawsuits aside, Greenberg and his wife have also had at least one personal lawsuit involving real estate.

The Greenbergs signed a contract to buy a house in a resort in British Columbia, but backed out of the sale saying certain repairs had not been completed in time. They sued for the return of a $100,000 deposit on the property. But a Canadian appellate court sided with the British Columbia real estate broker who filed a countersuit. The couple was eventually forced to pay a judgment of $610,000 following a court ruling that their decision not follow through on the purchase of the property cost the broker hundreds of thousands of dollars when the house was put back on the market at a much lower price during the real estate slump.

Both Esty and Greenberg have started to run ads. These early ads are aimed at selling voters on the competency and “niceness” of the candidates.

But the campaigns are expected to take the gloves off soon, and groups like the DCCC that are independent of the campaigns are also expected to fill the airwaves with attack ads.

Clarification: More specific comments by Greenberg supporter Michael Barnes have been included in this story. A characterization of his remarks in a previous version of the story was too general.