A Navy Pilot Tries to Flip a Key House Seat, Right by Trump’s Golf Club Rebecca Bennett, a Democrat, is vying to unseat Representative Thomas Kean Jr. in a New Jersey district that includes President Trump’s Bedminster golf club.

Rebecca Bennett is running to unseat Representative Thomas Kean Jr., a New Jersey Republican and son of a former governor. Credit...Bryan Anselm for The New York Times Supported by To Rebecca Bennett, the limitations of the MH-60 Seahawk she flew as a 20-something Navy helicopter pilot were striking. Its computer processors were too slow to load a moving Google map, she said. Floppy diskettes were the norm. And female pilots had nowhere to safely urinate on long flights. The problems, she said, seemed fixable, but not from a cockpit.

So Ms. Bennett, now 39 and running for Congress in one of the country’s most closely watched midterm races, applied in 2014 to the Navy’s elite Test Pilot School, where for a year she trained to assess and improve aircraft performance.

“To go try,” she said, “to make this stuff better.”That same mind-set, she said, led her to launch her first campaign for office soon after President Trump was elected to a second term. “I was like, ‘I’ve got to go throw myself at this problem,’” Ms. Bennett, a Democrat, said in an interview.

To get to Washington, she will first need to unseat Representative Thomas Kean Jr., a New Jersey Republican who shares a name with his father, a former governor.

The race was upended this spring after Mr. Kean, 58, disappeared from Capitol Hill for nearly four months, an absence he later said was tied to a long-term hospital stay for depression. Waning public support for the president and alarm over the high prices of gas, diesel and groceries have only added to Mr. Kean’s challenges.

Democrats see Mr. Kean’s Seventh District seat as one of their best pickup opportunities in Tuesday’s elections, in spite of the congressman’s formidable fund-raising advantage, which has helped to fuel a barrage of negative ads against Ms. Bennett, a former health care executive.

Mr. Kean and his Republican allies have tried to depict Ms. Bennett as too left-leaning for the affluent district and its most famous, part-time resident: Mr. Trump, who often spends time at his golf club in Bedminster. “She’s a greedy, liberal millionaire who doesn’t care about you,” intones an ad paid for by the Kean campaign.

But a review of Ms. Bennett’s life and career offers a far more complex portrait, one that appears to be resonating with voters in a state that a year ago elected another Navy helicopter pilot, Gov. Mikie Sherrill, by a resounding margin. In the final weeks of the campaign, officials with two Republican super PACs withdrew about $2 million in ads booked in support of Mr. Kean after internal polling showed his odds dimming; early Democratic turnout has been roughly twice the rate of Republican turnout in the northern New Jersey district.

‘Incredibly driven’Ms. Bennett spent 15 years in the Navy and the Air National Guard and was registered to vote as a Republican until she was nearly 30. She describes herself as a “patriot” at rallies where supporters hold signs that read “country over party,” a campaign slogan. In grad school at the Wharton School of the University of Pennsylvania, her similarly hard-charging M.B.A. classmates voted her “most likely to become president.”

It is a prediction that was tossed around in her childhood home in Granbury, Texas, too. Her sister, Sarah Matz, said it was a lighthearted nod toward Ms. Bennett’s tendency to “always go to the hardest thing.”At 16, Ms. Bennett moved 75 miles away from home and into a dorm room at the University of North Texas to begin two years of publicly funded college-level math and science coursework. At 18, she won an R.O.T.C. scholarship and entered Cornell University, where she studied chemical engineering.

When Ms. Bennett, the maid of honor at her sister’s wedding, recited a long speech from memory, Ms. Matz recalled: “My husband’s friends were like, ‘Your sister’s really intense.’”“She is incredibly smart. She’s incredibly driven,” Ms. Matz added.

“That’s who she is. She’s not trying to be anything else, you know?”Jeff Lindbom flew with Ms. Bennett in the Navy while she was deployed on the U.S.S. Nimitz in the Persian Gulf, during Operation Enduring Freedom. Their first flight together was a nighttime training mission, he said, and Ms. Bennett was his instructor.

The helicopter they were flying came too close to another. “A not-good situation,” he said. “Definitely gets the hair standing on the back of your neck.”Ms. Bennett took charge to get the pilots reoriented and in the coming days gave Mr. Lindbom, a friend, a failing grade. Her high standards helped to shape him as a pilot, he said; years later, he would follow her to Test Pilot School.

The school, founded in 1945 and based in Patuxent, Md., is known for its rigor. Twenty-two of its graduates, including a woman who graduated with Ms. Bennett in 2016, have gone on to become astronauts since 2000, according to a spokesman for NASA.

To save time commuting during the yearlong program, Ms. Bennett put a mattress on the floor of a classmate’s condo and returned home on weekends to see her husband, who at the time was also on active duty in the Navy.

“She knew what it would take to succeed in that kind of environment,” the classmate, Kristine Sweigart, said. “She literally lived on my floor for a year so that she could excel.”That was also the year that Ms. Bennett’s politics began to shift toward the Democratic Party. ‘I cannot sit in this church’In 2016, Mr. Trump, then a New York City businessman, was ascendant.

Ms. Bennett changed her party affiliation that summer and made what she said was her first-ever political contribution, to Mr. Trump’s Democratic opponent, Hillary Clinton.

One of Ms. Bennett’s first television ads emphasized the apolitical nature of the military. “In the aircraft,” she says, “you’d never ask your crew if they’re Democrats or Republicans.”But after leaving the Navy in 2022, Ms. Bennett did fully jump into partisan politics, participating in phone banks for Democratic candidates and traveling to Michigan with her sister to knock on doors in support of Vice President Kamala Harris’s presidential bid.

She has told supporters that her frustration with Mr. Trump’s 2016 victory briefly led her to stop attending church in Maryland, according to a recording first reported by The Washington Free Beacon.

“I was like, ‘I cannot sit in this church full of people who voted for Trump,’” said Ms. Bennett, a Presbyterian. “Then, ultimately, I decided they do not get to decide what Christianity looks like.”Mr. Kean has said the disclosure shows that Ms. Bennett is incapable of working across the aisle in Washington.

“That’s not a person who’s going to listen,” he told a debate audience. After moving to New Jersey in 2019, Ms. Bennett became active in a Presbyterian Church (U.S.A.) congregation in Princeton that is known for its inclusive services. David A. Davis, the church’s pastor, said she sought his counsel soon after Mr. Trump was elected in 2024. She was deciding, he said, whether to enter the race against Mr. Kean, aware it would “upend her life.”Some of Ms. Bennett’s earliest campaign videos, he noted, were filmed at Nassau.

It was a deliberate choice for Ms. Bennett, who said that her “sense of service” was heavily shaped by the church-led mission trips she participated in as a teenager in Texas. “We were not wealthy,” she said. “But we had a roof over our head and we had food.

“Going to places in the country and seeing people who do not have that, it just made me very appreciative of what I was given.”Early in the campaign, as she tried to set herself apart from Mr. Kean, Ms. Bennett frequently referred to the 2010 Honda Accord she drove. Mr. Kean comes from a wealthy New Jersey political family; his estimated $10 million in assets are linked largely to family trusts.

Yet during the debate, Ms. Bennett refused to state her own net worth, instead referring people to her financial disclosure forms, which show assets worth between $430,000 and $1.5 million, including two I.R.A.s and college savings plans.

Ms. Bennett and her husband also own a four-bedroom home in Montgomery, N.J., a suburban township that lawmakers excised from the Seventh District when redrawing congressional boundaries after the 2020 census.

House members are not required to live in the district they represent. But the new map created a public relations challenge for a candidate hoping to kick Mr. Kean — whose deep New Jersey roots extend to the state’s first governor — out of office.

During the summer of 2025, she and her husband moved into a rental home about 15 miles away in Bridgewater, which is in the Seventh District. Their 7-year-old daughter attends public school there and their 4-year-old daughter is in day care nearby. ‘The best of the best’The race began as one of only a handful of tossup battleground contests in the 2026 midterm cycle and was regularly cited by both parties as a must win, drawing prominent surrogates to the campaign trail.

Gabby Giffords, a former congresswoman and a leading gun-control advocate, joined Ms. Bennett this month at a library in New Providence. The Democratic House leader, Hakeem Jeffries, spent a recent Friday night with Ms. Bennett at a small Baptist church in Linden. Pete Buttigieg, a former transportation secretary, spoke to a large crowd at a community college in Branchburg, hailing Ms. Bennett’s military experience as the “perfect background for going to the United States Congress in today’s Washington.”“A test pilot — the best of the best — whose job is to figure out what’s broken before anybody gets hurt,” he said.

Before entering the race, Ms. Bennett worked for four health care companies — Johnson & Johnson, Midi Health, Noom and Oshi Health — and she has made repealing the deep cuts to Medicaid that Mr. Kean supported as part of the president’s so-called Big Beautiful Bill a central campaign platform. She has also called for modernizing the country’s air traffic control system, ending the war with Iran and freezing child care costs at 7 percent of a family’s income.

Ms. Bennett’s own child care costs have become a Republican talking point, after campaign filings showed she used roughly $20,000 in donations to pay for her daughter’s day care, a decision Mr. Kean has attacked. Ms. Bennett’s campaign has noted that the Federal Election Commission has since 2018 permitted candidates to use campaign contributions to pay for child care “to help parents who aren’t independently wealthy be able to run for Congress.”

Republicans have also homed in on Ms. Bennett’s work in health care in ads that suggest she led efforts to put profits over patients, highlighting her role at Midi in brokering a partnership with a private-equity-backed hospital chain. “She bragged about her deals with sketchy companies,” reads a mailer that includes a photograph of a bloody, disembodied eye.

Cindy Gentry, Ms. Bennett’s boss at Midi, a start-up focused on expanding telehealth for menopausal women, said the advertising “missed the point.”“The point is women didn’t have access to care,” Ms. Gentry said. “What Rebecca was trying to do, was, ‘How do I create telehealth offerings that expands access and provides good, high-quality care to women who right now don’t have access to it?’”

In early October, Ms. Bennett and Mr. Jeffries sat side by side at Greater Mount Moriah Baptist Church, in front of pews packed with Democratic loyalists. The pastor, the Rev. Barry Wise II, used the opportunity to note his disappointment with Democrats who fail to follow through on promises after being elected, pointedly urging Ms. Bennett — and Mr. Jeffries — to do better. Ms. Bennett, in her remarks, turned to face Pastor Wise.

“I will wake up every day,” she said, “and work harder than I’ve ever worked in my life to fight for you and your family as hard as I fight for my own kids.”