From Newhallville to Madison: Bob Stefanowski pitches working-class upbringing in gubernatorial battle of millionaires

Decades before he became a multimillionaire, Bob Stefanowski slept in a walk-in closet.

Life was not luxurious in a three-family home in a hardscrabble neighborhood off Dixwell Avenue in New Haven.

Stefanowski’s parents worked hard, saved their money and eventually moved the family to a small, two-bedroom home in North Haven that his father still owns. It was there that Stefanowski says he slept in the closet for years.

But Stefanowski, the Republican candidate for governor, returned to the city recently and walked along the New Haven streets with reporters following him. He stopped and told stories about his younger days in a three-family home at 40 Pond St., a residential road off the commercial strip of well-traveled Dixwell Avenue.

Stefanowski walked through his old neighborhood to draw a contrast with Gov. Ned Lamont at a time when both candidates are essentially self-funding their campaigns. Stefanowski has pledged to spend $10 million of his own money, while Lamont is expected to spend as much as the $15 million that he spent to defeat Stefanowski by three percentage points in 2018.

“People say we’ve got two rich guys running for governor. I’ll admit it. I’ve done pretty well,” Stefanowski said outside the local, family-owned pharmacy where he bought ice cream in his youth. “But one of the two guys running grew up in Greenwich, Connecticut, going to the polo grounds on the weekend. I grew up here. Terrific upbringing. We had a three-family house. We lived on the bottom floor. My grandparents lived on the middle floor, and we had Southern Connecticut [State University] students on the top floor. … Next door is the grammar school I went to, which is now a methadone clinic. Democrats have been in charge of the cities for 40 years now. I think we can do better.”

During a tour with reporters, Stefanowski said he believes that Lamont, a Democrat who has protected funding for social programs, cannot empathize with struggling families.

“Unless you’ve grown up sleeping in a closet, which I did … I just think it’s hard to empathize,” Stefanowski said during the tour. “It’s like saying you know what Australia is because you took a trip to Australia. … I don’t think Gov. Lamont has a real appreciation for what people are going through, and if he did, he wouldn’t be running ads saying that everything is fine and he’s done as much as he can. Do you think that people in this neighborhood feel like Gov. Lamont has done as much as he can, especially when he’s sitting with $6 billion [in state reserves]? It’s just not right.”

But in a recent interview with The Courant, Lamont — who grew up on Long Island, not in Greenwich — rejected Stefanowski’s notions about personal wealth.

“I don’t need to take any lectures from a guy who lives in a big house in Madison and is putting $10 million into his campaign,” Lamont said. “It’s not where you’re from. It’s where you stand, and I think people know where I stand.”

Leaving New Haven

With reporters watching, Stefanowski walked down the New Haven driveway that he had shoveled during storms in the early 1970s as a young boy.

“I broke this window with a whiffle ball once,” Stefanowski said, pointing to the next-door home as his running mate, Rep. Laura Devlin, laughed. “This was Mrs. Lynch. She had a dog named Linnie. My dad and I were changing that gutter once for Mrs. Lynch and bees came out. … You know how there’s certain things you remember as a kid? I can remember the bees being inside my shirt.”

Stefanowski cautioned several times that he was not lamenting his childhood.

“I’m not telling you a sob story,” Stefanowski said. “It was a great upbringing. I loved it here. You didn’t want to move. You shouldn’t have to move.”

Born in 1962, Stefanowski moved out of New Haven with his family when he was in second grade. He said his parents could no longer afford the Roman Catholic school on Dixwell Avenue in the neighborhood.

He grew up mainly in North Haven and attended the town’s local public high school.

“I didn’t want to move out,” Stefanowski said of his younger days. “I didn’t want to leave my grandmother. They didn’t want to move out, but they found the best community where they could afford a house. They got the average house price, and they bought a house in North Haven for 25,000 bucks. Two bedroom with a closet. It was a big closet. Walk-in closet.”

With three older sisters, two parents and himself, Stefanowski said it was sometimes difficult getting into the home’s only bathroom in the morning. He repeated the story Friday to an audience of business executives at a forum sponsored by the Connecticut Business and Industry Association at a downtown Hartford hotel.

“I was in a walk-in closet. It was fine when I was in third grade, but when I got over 6 feet, I had to start curling up my feet,” Stefanowski told the crowd.

Lamont’s campaign, though, says the anecdotes do not tell the whole story of Stefanowski’s business career that includes being chief executive officer of a payday lending company.

“Bob likes to pretend he’s a working person,” said Lamont spokesman Jake Lewis. “But he must have forgot about where he came from or who his neighbors were, as he made millions of dollars from ripping off working families who were desperate to pay rent or keep afloat by offering them loans he knew they couldn’t pay back, that only send them further into debt.”

Polls and pundits

Gary Rose, a longtime political science professor at Sacred Heart University in Fairfield, said that Stefanowski promoting himself as a self-made millionaire is a solid political strategy that should be working. But Rose said the recent polling shows that the strategy is not working.

Lamont leads in multiple polls, including the latest Quinnipiac University survey that showed him ahead by 17 points with a margin of error of plus or minus 2.2 percentage points. A separate survey by Emerson College Polling that was released by Channel 8 showed Lamont with a 10-point lead with 9% still undecided.

Stefanowski blasted the Quinnipiac survey as “laughable,” saying his internal polls show that the race is within the margin of error. But political insiders said Stefanowski would not have dismissed his campaign manager and chief strategist in August if the race had actually been that close. Lamont said his internal polling is relatively close to the Emerson margin, and Democrats say Lamont’s large lead in the Quinnipiac poll is not surprising.

Despite the polls, Rose said the concept of an up-by-the-bootstraps executive should be appealing.

“At a time when people are frustrated with government and frustrated with the economy, you would think that message would be gaining traction, but apparently it’s not,” Rose said in an interview. “Maybe it’s not being articulated and presented in a way that’s really effective. … That’s why his ads show him in diners with the common folk. It’s a good strategy, but it doesn’t seem to be resonating. Somehow, it’s not working.”

Both Rose and Quinnipiac University political science professor Scott McLean said that Lamont is seen as a wealthy individual who reaches out to less-affluent voters in the tradition of Democratic Presidents Franklin D. Roosevelt and John F. Kennedy, who both came from wealthy families.

“What Stefanowski is trying to say is he’s more of a self-made millionaire,” McLean said. “Lamont is not. He comes from a family of millionaires.”

Big earnings later in life

Stefanowski started on the long road to becoming a multimillionaire after gaining a solid education.

After graduating from Fairfield University with a bachelor’s degree in accounting in 1984, he worked as an auditor in Hartford for five years for Price Waterhouse, an accounting giant that later merged with other firms. Stefanowski began to obtain much bigger jobs after receiving an MBA from Cornell University. He joined General Electric, an iconic manufacturer that at the time was among the largest, most powerful companies in the nation.

Stefanowski spent 13 years at GE, including five years as director of mergers and acquisitions at GE Commercial Equipment Finance. He also served as president and CEO at GE Commercial and Industrial Finance from 2003-2004, president and CEO at GE Telecom, Media & Technology Finance from 2004-05, and president and CEO at GE Corporate Finance, Europe, Middle East & Africa with more than 2,500 employees and gross revenues of more than $3 billion annually.

As a consultant, Stefanowski earned $29 million during 2020 and 2021 — helping fuel his current run for governor.

Stefanowski’s federal tax returns showed total income of $15.7 million in 2020 and $13.6 million in the following year during the COVID-19 pandemic. The spike in 2020 marked a sharp uptick from the previous year of $7.38 million.

After earning $36.8 million in total income in three years, Stefanowski has now set aside $10 million to fund his current campaign — more than triple his total for the 2018 battle against Lamont. The two multimillionaire former business executives have been running numerous television commercials on a variety of channels in a slugfest that has already lasted for months.

While Stefanowski earned $36.8 million in three years, Lamont earned $26 million in three years from 2018 through 2020. Lamont has not released his 2021 tax returns because he filed for an extension. Summaries of returns showed that Lamont had adjusted gross incomes of $7.7 million in 2018, $10.14 million in 2019, and $8.0 million in 2020.

McLean, the Quinnipiac professor, said that Stefanowski — despite running in 2018 — is still not a household name and is not as well-known as Lamont.

“Stefanowski is still kind of a mystery to a lot of people,” McLean said in an interview. “Stefanowski is terrific in small groups and gets to know people very well, but he’s not widely known. That’s the incumbent advantage. That’s what Stefanowski’s up against. Like him or not, you have an image of who Lamont is and what he is about. Stefanowski can still be a bit of a mystery to most voters who are only just now starting to pay attention to this race.”

Based on his studies of political science and public opinion, McLean said that the average voter often forgets the details about a particular candidate from the past.

“People tell us in so many examples that someone who has run before and people ought to know, when they run again, people say, ‘I don’t know them very well. I need to know more about them before I decide if I even like them,'” McLean said. “When you run again, you have to reintroduce yourself all over again to a lot of people. That’s part of the challenge of not being the incumbent. Even though he ran before, people need to get to know him again.”

Christopher Keating can be reached at ckeating@courant.com.