Kerry Woolard, general manager of Trump Winery in Charlottesville, Virginia, spoke to the MassGOP delegation in Cleveland on Monday. [Photo: Matt Murphy/SHNS]
CLEVELAND — As the curtain rose on the Republican National Convention Monday, enthusiasm among Massachusetts Republicans for presumptive nominee Donald Trump was tempered by lingering doubts about the candidate among some representing the state in Cleveland.
While most of the 42 delegates representing the state have backed Trump from the beginning or come around to the candidate, some remain more reluctant to jump on board with Trump and are looking for signs in the coming days that he can be the candidate they’re looking for.
Binding them all, however, appeared to be agreement that Hillary Clinton, who will accept the Democratic nomination in Philadelphia next week, should not become the next president.
“I think we’re loyal Republicans. I think we all are motivated by winning and giving the country an alternative to Hillary Clinton and I think our delegation represents our strong totals on Super Tuesday,” said Dean Cavaretta, a delegate and state director for the Trump campaign in Massachusetts.
After many took in the fireworks over Lake Erie Sunday night at a welcome party that featured a performance by Three Dog Night, delegates on Monday morning were visited by Kerry Woolard, the general manager of Trump Winery in Charlottesville, Virginia.
Woolard said Trump, if elected, would be the first president since Thomas Jefferson to own a winery, a 1,300 acre estate whose wines are distributed in Massachusetts by Martignetti Companies.
Wollard also spoke about Trump as a visionary leader who dares to “think big” and challenges his employees to rise to the task. But in response to questions from several delegates about controversial comments Trump has made toward women, she also found herself defending the man for whom she’s worked five years.
Wollard said the Trump organization “may be the only company I’ve ever worked for where being a woman hasn’t come into play,” and said she has never once been treated disrespectfully.
“This is not because of the campaign. This is not in the last few years thinking maybe of running for president and trying to beef things up. This goes back 30 years,” Wollard said of Trump’s history of supporting women in the company.
Her comments went over well with the delegation, and jbed with what one elected official who was once skeptical of Trump has come to believe over time about the brash New York businessman.
Rep. Keiko Orrall, who is a credentialed guest at the convention and will take over as Republican national committeewoman from Massachusetts on Friday, once said of Trump that she took “great offense to the things he’s said about women and minorities.”
“I find it unbelievable that he is out in front because he is saying things that are not Republican; they’re not Republican values,” Orrall told the News Service last August.
Orrall, who supported Florida Sen. Marco Rubio during the primaries, now believes she may have been mistaken about Trump.
“A lot has changed since August of last year. I have come to understand that he’s a big personality. That’s the way he communicates, but in general I don’t believe he’s a racist. I don’t believe he’s against women. I just don’t,” Orrall said on Monday.
Orrall now supports Trump, in part because of her belief that someone who has been under investigation by the F.B.I. as Clinton has should not become president. “I believe that’s the direction that our country wants to head and I believe that he’s the person that’s going to make America safe again,” she said.
Jim Rappaport, a delegate and former chair of the Massachusetts Republican Party, has not been so convinced.
“I’m a firm believer that nobody owes support to a candidate. A candidate has to earn that support and today he hasn’t earned my support,” Rappaport said on Trump. “I’m open to supporting him because I think Hillary will be so bad for the country, but let me put it this way. An Uber driver said to me a couple weeks ago in California, ‘350 million people in this country and this is the best we can do?'”
Rappaport, who supported Ohio Gov. John Kasich for the Republican nomination, said he did approve of Trump’s selection of Indiana Gov. Mike Pence as a running mate, but will need to see more from Trump if he’s to vote for him in November.
“I want to see if he can in fact act presidential. I don’t need him to be politically correct because I’m not politically correct but I don’t need him to be offensive,” Rappaport said.
In many ways, this year’s convention has shown how much can change in politics in four years.
Instead of the red-carpet treatment of staying at the same hotel as the nominee – as the Massachusetts delegation did with Mitt Romney in Tampa in 2012 – delegates are staying 17 miles away in Beachwood, Ohio.
The cast has also changed. The delegation this year is a mix of veteran party operatives and first-time activists instead of the cadre of elected officials who turned out in Tampa to help nominate Romney, one of their own.
Ron Kaufman, a top advisor to Romney and Republican national committeeman, told delegates Monday morning that the convention was going to be a “fun party,” but neither he nor MassGOP Chairwoman Kirsten Hughes spent much time talking about Trump directly.
Hughes, who is technically a Rubio delegate, but now backs Trump, noted that the theme for the first day of the convention will be “Make America Safe Again.
“It points to the continuous failure of Democrats to make America safe,…” Hughes said. “We know Republicans have the answers on safety.”
Kaufman also said the next four days will be an opportunity for the delegates and America to learn more about Trump as a person, remarking how Romney may have won the presidency had the film “Mitt,” which was an intimate behind the scenes documentary about Romney, been released before and not after the 2012 election.
“Most of us really don’t know who Donald Trump really is,” Kaufman said.
Kerry Woolard, general manager of Trump Winery in Charlottesville, Virginia, spoke to the MassGOP delegation in Cleveland on Monday. [Photo: Matt Murphy/SHNS] 
