Bob Stefanowski is the latest in a series of outsiders from the world of business to win a Republican primary for top-of-ticket statewide offices in Connecticut, none of whom were able to beat their conventional Democratic opponents in the fall.
But those races for governor and U.S. Senate came before the ultimate outsider, Donald J. Trump, captured the White House.
And none of them followed the path taken by Stefanowski to victory Tuesday night.
For the first time in Connecticut, the GOP’s gubernatorial nominee is a candidate who bypassed the state nominating convention, whose 1,100 delegates were thought to control access to the party’s primary. Instead, his campaign focused time and resources on a petition drive that introduced the political newcomer to 16,000 Republican voters.
Those voters not only provided the signatures that qualified him for the primary, they became the core of a voter data base — a collection of names and addresses that the campaign regularly used to promote Stefanowski and the central theme of his campaign: a pledge for no new taxes, and a promise to eliminate the income tax over eight years.
“That was the game changer,” said Patrick Trueman, his 30-year-old campaign manager. “That was the complete game changer.”
Stefanowski began the general election campaign Wednesday trading Twitter barbs with the Democratic nominee. The Twitter spat with Ned Lamont centered around whether Lamont was more like the unpopular Democratic governor or Stefanowski was closer to the unpredictable Republican president: “Bob Trumpanowski” vs. “Ned Malloy.”
“I think the Democrats are going to do everything they can not to talk about the Connecticut economy, which is what people care about,” Stefanowski said in an interview Wednesday. “The reason is there is no way they can talk about what Dan Malloy did to Connecticut for the last eight years.”
Stefanowski introduced himself to Connecticut voters in December with an audacious, even Trumpian, promise. With the support of the supply-side economist Arthur Laffer, whom he hired as a campaign consultant, Stefanowski promised to cut spending deeper than any previous governor for two years, then spend the next six years phasing out the state income tax, assuming his re-election in 2022.
Lamont likens the promise to Trump’s insistence he will wall off the U.S. from Mexico, and Mexico will pick up the tab. On Wednesday, Stefanowski allowed that the plan is a rallying cry, a statement of where he wants to bring Connecticut — not necessarily a detailed map on how to get there.
“I think it’s an aspirational goal that I’m going to try my best to deliver,” Stefanowski said. “If I didn’t think we didn’t have a good chance to get it done, I wouldn’t say it.”
Conversely, he said, Lamont already has said he expects to seek additional revenues, either from electronic tolls, higher taxes on the wealthy, or both. Even though Lamont’s previous interactions with Gov. Dannel P. Malloy have been hostile — they were combatants in a bruising Democratic primary in 2010 — his embrace of tolls and a search for more revenue make him a conventional Democrat, one whom Stefanowski says can reasonably be compared to Malloy.
Stefanowski said he is comfortable with people thinking his income tax plan is unrealistic because it establishes a goal and a tone.
“People want optimism,” he said. “People don’t want to hear what you can’t do.”
Stefanowski said his campaign not only will contrast his record of managing sprawling business units in the U.S. and abroad with Lamont’s stewardship of a relatively small company, but will compare Stefanowski’s upbringing in a blue-collar North Haven neighborhood with Lamont’s status as the great-grandson of Thomas W. Lamont and grandson of Thomas S. Lamont. The former was the chairman of J.P. Morgan and the latter was a partner at Morgan Guaranty Trust.
“I do look forward to running against Ned Lamont,” he said. “I think the contrasts work in my favor.”
Roy Occhiogrosso, a Democratic consultant and former adviser to Malloy, said he was stunned the GOP once again went with a business outsider, instead of nominating Mark Boughton, the centrist mayor of Danbury, for governor. Voters also rejected Erin Stewart, the socially moderate 31-year-old mayor of New Britain, as his running mate. Boughton ran second to Stefanowski, and Stewart ran second to state Sen. Joe Markley, one of the most conservative members of the General Assembly.
“It’s like they can’t help themselves,” Occhiogrosso said.
Whoever wins in November, Connecticut’s next governor will be the first in decades to govern with no government experience. Lamont has more political experience as the Democratic nominee for U.S. Senate in 2006 and a gubernatorial candidate in 2010, but he, too, is from the world of business. Lamont is the founder and former owner of a cable television company that serves college campuses.
Stefanowski said the political atmosphere is different today than in 2010, when two wealthy business executives, Tom Foley and Linda McMahon, self-funded campaigns for open seats — Foley for governor and McMahon for Senate. It is also different from 2012, when McMahon tried again, or 2014, when Foley had a rematch with Malloy. As Trump showed, the electorate is hungry for an unconventional leader, even if he is not exactly cut from the Trump mold.
Stefanowski, 56, who is married with three daughters ages 15, 19 and 23, is the professional product of corporate America and U.K. financial companies, not Trump’s existence as a swashbuckling real-estate developer and reality TV star whose biggest commercial and political asset is his personal brand.
Stefanowski is an MBA who rose through the ranks at GE under Jack Welch, eventually leading three business units and then becoming the CFO of UBS Investment Bank and CEO of DFC Global, a pay day loan company in the U.K. and U.S.
On Wednesday, Stefanowski said the campaign was “10 times harder” than he imagined it would be, an assessment offered as an observation, not a complaint. He recalled the difficulty in seeing the first negative ad directed at him, knowing his daughters would see it.
“It toughens you up,” he said. “The first negative press release, you read it 50 times.”
The subsequent ones, he said, you let go.
He said his four rivals in the primary — Boughton, Timothy Herbst, Steve Obsitnik and David Stemerman — were good sparring partners.
“They are tenacious. They just would not give up. You think you get them down, and they pop up,” he said. “They are tenacious. I think it’s good training for the general.”
On Thursday, he drives his middle daughter to Cornell University in Ithaca, N.Y., where he went to business school for his M.B.A. It’s a nine-hour roundtrip drive, providing time with his wife, Amy.
On Monday, he meets with the GOP’s chairman, J.R. Romano, and its other nominees for statewide office, in his first formal role as the new leader of the Republican ticket.
That’s when the outsider will get his first taste of the inside.