The state hasn't exactly been friendly territory for Republicans lately.
"Connecticut is an incredibly, incredibly blue state," said two-time GOP Senate candidate Linda McMahon, a delegate to this week's Republican National Convention.
But with Trump at the top of the ticket, McMahon thinks there's a chance her state will go red, and she credits her own two failed campaigns for awakening Republicans in the Nutmeg State.
The co-founder and former CEO of the professional wrestling company WWE, McMahon has known Trump for 30 years — mostly through business. "We're not close social friends," she said, sitting in a private lounge on the fourth floor of the Quicken Loans Arena overlooking the convention floor.
As a northeastern Republican best known for her role in the entertainment business and for pouring nearly $100 million of her own money into her campaigns, McMahon's political trajectory wasn't all that different from Trump's.
On policy, too, she sees an affinity. She's fiscally conservative and socially moderate.
“He has said he’s a pro-life candidate, so we may be a little different on that," McMahon said of the GOP nominee. But she suspects there's not all that much room between herself and the New York real estate mogul on other social issues.
This isn't McMahon's first convention, but it's a little different from what she's experienced in the past.
McMahon sat with a shawl over her shoulders — she'd had frozen yogurt for a late lunch, the leftovers of which she instructed an aide to toss — and it was icy in the lounge.
She recalled roaming the floors of both the Democratic and Republican conventions in 2000 and 2004 as part of WWE's "Smackdown Your Vote!" programming to encourage young people to vote.
This year marks McMahon's first time as a delegate, and as a member of the rules committee, she strongly supports delegates being bound to the candidate who won their state. Trump won the Connecticut GOP primary in April with close to 60 percent of the vote.
On Tuesday night, it was almost time for her to head down to the convention floor for the delegation to cast their votes. But she had to leave extra time to get there because of a still-healing foot after surgery that has rendered her reliant on a motorized scooter.
That's meant no parties. After the convention programming each night, she's back in her room to ice her foot.
But McMahon's enjoying just being in Cleveland. She ran into Tennessee Sen. Bob Corker over dinner at the Ritz Carlton, and she was smitten when Dan Rather held the door open for her scooter.
And although she didn't start out backing Trump — she hosted two fundraisers for New Jersey Gov. Chris Christie at her house during the early part of the campaign — she's all in for Trump now.
Christie campaigned for her both in 2010, when she ran against Richard Blumenthal, and in 2012, when she ran against Christopher S. Murphy. Trump also supported her in those two races, both of which she lost by 12 points.
During both campaigns, McMahon faced many of the same attacks Trump has this season — for ties to an entertainment business criticized as unsavory, and for trying to buy political power.
During that first Senate campaign, McMahon didn't accept donations.
"I felt it was a bonus to use my own money because I said out-front I won’t be beholden to any lobbyists," she said. Trump made the same argument throughout the primary season, and on Wednesday, he officially forgave all the personal loans he'd made to his presidential campaign.
Trump is funding 55 percent of his own campaign, according to an analysis by the Center for Public Integrity .
Self-funding opened McMahon up to attacks that she was buying the election, she said. So when she ran two years later, she accepted donations. The problem was, no one wanted to give to her because they all knew she didn't need the money as much as other candidates.
While McMahon says she's done running for office, she's now helping other female Republicans like New Hampshire's Kelly Ayotte, Arizona's Martha McSally and New York's Elise Stefanik.
"I don’t have that desire to run again," she said.