Timothy Herbst mark pazniokas / ctmirror.org
Timothy Herbst consulting with his father at a GOP forum in January. mark pazniokas / ctmirror.org

Timothy Herbst is in a good mood. At the Cromwell Diner, where he just chatted with the mayor and former police chief over a breakfast of coffee, eggs and politics, he says he can see a path through a crowded field to the Republican nomination for governor — even if it means stealing a page from the GOP’s bête noire, Gov. Dannel P. Malloy.

Herbst finished second to Danbury Mayor Mark Boughton at the Republican state convention, but he arguably emerged as the winner. His competitor for the conservative base, Peter Lumaj, failed to qualify for the mid-summer face-off  — a primary on Aug. 14 featuring Boughton, Herbst, tech entrepreneur Steve Obsitnik of Westport and up to three others now petitioning for a spot.

With room to roam on the right, Herbst now is free to draw distinctions with the rest of the field, asking Republicans to assess who best lines up against the presumptive Democratic nominee, Ned Lamont, the first of the two wealthy, self-funding Greenwich candidates an underfunded Malloy beat in 2010. The second was Republican Tom Foley.

“I am happy where I am right now,” Herbst says.

Herbst, 37, a dark-haired lawyer who ended an eight-year run last year as the first selectman of Trumbull, a comfortable Bridgeport suburb with a population of 36,477, has seemed to work hardest, or at least most publicly, to define the race since he left the hurly burly of the convention floor at Foxwoods for a shower and a sip of Japanese whisky, a gift from a friend.

He was the first to go on offense, challenging Republicans to 10 debates before the primary. In 2010, Malloy left his convention by challenging Lamont to 17 debates, one in every city and town with a daily newspaper. The question of debates became something akin to a small chronic toothache for Lamont — not disabling, but annoying.

Herbst, who never has been afraid to be annoying, took notice. He has studied the tactics Malloy employed against Lamont, then Foley.

“The one thing I admire about Dan Malloy is his tenacity and his grit,” Herbst said. “We agree on not much, but he is a tenacious campaigner, and he has a tremendous work ethic. In that perspective, from a campaign perspective, in terms of elections, I can relate to him.”

Timothy Herbst talks to voters at the Cromwell Diner. Unfortunately for him, neither was eligible to vote in the GOP primary. mark pazniokas / ctmirror.org

On this day, after signaling for another mug of coffee, Herbst is ready to get gritty, comparing himself to Boughton and Obsitnik. They and Herbst were the only three of the eight candidates nominated at the convention to win 15 percent of the delegate vote, automatically qualifying for the primary.

“Which of the three of us presents the most clear, the most distinct contrast to Ned Lamont?” Herbst asked. “I think of the three of us, I’ll be the most clear and distinct contrast in this sense: You’re not going to beat a retread candidate with a retread candidate. Ned Lamont has run twice for governor. Mark Boughton has run three times for governor.”

Unsaid is that Herbst now has run twice for statewide office. In 2014, he won the GOP nomination for state treasurer, losing a close race in November to Denise L. Nappier, a Democrat seeking her fifth and final term.

Herbst casually, almost sympathetically insults Boughton, the convention-endorsed candidate, saying he would happily have deferred to the long-time Danbury mayor — if only he thought Boughton had the stuff to win on his third time out.

“Look, I wouldn’t be in this race if I thought Mark had the assertiveness, the strength, the fortitude, the grit to make the tough decisions to do what needs to be done,” Herbst said. “I just don’t think he has it in him. And I wouldn’t be in this race if I thought he did.”

Boughton and Obsitnik largely ignore the gibes, though Boughton responded to the debate challenge by telling The Courant, “We don’t let our campaign cave to a Timmy temper tantrum.”

Obsitnik, a graduate of the U.S. Naval Academy who became a tech entrepreneur after service aboard a fast-attack nuclear submarine, said he is focused on promoting his ideas for economic growth and fiscal stability.

“I will talk about that anywhere, any time with anybody,” Obsitnik said. “That’s what the voters of Connecticut want to talk about. They don’t want side shows.”

On Monday, June 11 at 7 p.m., Herbst, Boughton and Obsitnik will debate at the Shubert Theater in New Haven. The debate is sponsored by the Connecticut Realtors in partnership with WTNH, Channel 8.

Two other Republicans, David Stemerman of Greenwich and Bob Stefanowski of Madison, bypassed the convention to focus on qualifying by petitions, gathering signatures from 2 percent of GOP voters by 4 p.m. on June 12. Both are wealthy businessmen, largely self-funding their campaigns. Shelton Mayor Mark Lauretti competed at the convention and also is petitioning.

Herbst ignores Lauretti, but does not overlook Obsitnik, Stefanowski or Stemerman. He said the businessmen would offer insufficient contrast with Lamont, a cable-television entrepreneur and scion of a wealthy family.

“A Fairfield County millionaire against another Fairfield County millionaire is not the recipe, I think, for success for Republicans in November,” Herbst said, perhaps overlooking that Madison is in New Haven County. His larger point is class: Herbst describes himself as the son of public school teachers, who put himself through law school and “is not a trust-fund baby.”

Timothy Herbst and Mark Boughton at the GOP convention ctmirror.org

“I think that is going to help us in blue-collar cities and towns across Connecticut where Tom Foley should have won and didn’t win,” Herbst said. “So I will get get those suburban outliers like East Haven and North Haven and Milford and Stratford.”

Herbst made strong appeals to the conservative base before the convention, opposing Malloy’s choice of Andrew J. McDonald as chief justice of the Supreme Court and calling for the reinstitution of capital punishment. He was endorsed by the conservative Family Institute of Connecticut, which opposes abortion and same-sex marriage. While Herbst says those issues are settled law, he would back the institute’s call for requiring parental consent for abortion by minors.

Herbst’ age was a liability when he ran for first selectman as a 29-year-old and then, to a lesser degree, for state treasurer as a 33-year-old.

“I have to tell  you, I do believe in my heart that this is not only the most important state election of our lifetime, I believe that this is a generational election,” he said. “I believe it’s a generational election where the voters of the state of Connecticut, Republican primary voters first on August 14th, are going to be faced with a question: Do we want to continue to elect people from a generation that got us into this mess, or do we want to elect a new generation of leaders that are committed to fixing this mess?”

His age brings another advantage aside from a generational appeal, he said. Herbst, who says his heath is excellent after the removal of a cancerous thyroid 14 months ago, said he is the Republican most prepared for the physical rigors of campaigning, referring several times to “stamina.”

“I’m going to have the stamina to not only get through a primary, but to get through a tough general with Ned Lamont. This is Custer’s Last Stand for him. He’s going to pour whatever it takes of his own personal fortune to win,” Herbst said, adding that Democrats know the GOP is close to winning control of the General Assembly. “So it’s really going to take a candidate who has the physical stamina to get through the rigors of what’s going to be a very tough campaign.”

Um, could the repeated stamina references be a jab at Boughton, who had surgery to remove a non-cancerous growth from his brain in 2017, then experienced a seizure while campaigning in March?

“I’m not saying anything about Mark Boughton. I’m not talking about anybody’s health, but mine,” said Herbst, who also mentioned his fondness for CrossFit workouts. “But I know this is going to be a grueling campaign.”

Boughton, whose physicians briefed the press on his fitness, said his health is fine.

“In terms of my health and fitness, I’m ready to go. I probably do more work by 8 a.m. than he does all day,” Boughton said. “I don’t think people can doubt my stamina and readiness for the job.”

In trying to be different, Boughton said, Herbst was just being the same: “I think he is trying to do anything and everything to get elected — like the rest of us are.”

Correction: The date of the New Haven debate is incorrectly reported in the original posting of this story.

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Mark PazniokasCapitol Bureau Chief

Mark is the Capitol Bureau Chief and a co-founder of CT Mirror. He is a frequent contributor to WNPR, a former state politics writer for The Hartford Courant and Journal Inquirer, and contributor for The New York Times.

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