In golf, “The Dance” is what you call it when you make it to the green, ready to putt out. For Rob Churchill, it’s more than slang it’s a way of living. Sometimes you rush in, other times you take a breath and read the break. Either way, Rob’s been dancing to his own rhythm for years, navigating from New England fairways to the comedy stages of Florida.
Born and raised in Quincy, Massachusetts, Rob was a fixture at President’s Golf Course and a standout on the Quincy High School golf team, serving as captain all four years after walking on as a freshman. College didn’t hold his attention for long; he gave Florida Atlantic University a try for a year but quickly realized he was more interested in being a workin’ man rather than sitting in a lecture hall.
A Career Born by Chance
Before golf became a paycheck, Rob dabbled – EMT school, odd jobs, figuring it out like most of us do in our twenties. But fate had other plans. One afternoon, while casually helping someone with their swing, Rob heard words that changed his course “You could make money teaching this.” Soon after, he left EMT school and took a job in the locker room at Wollaston Golf Club in Milton.
Click to Listen! WATD SPORTS AUDIO EXTRA: Quincy Native Rob Churchill’s 1st Golf Swing
By 2003, he had earned his way to Assistant Golf Professional. He went on to work at several top-tier New England clubs, a season at Winthrop, a couple of years at Blue Hill and five years as First Assistant at Presidents before wrapping up his final season in the Boston area at LeBaron Hills. In 2013, he made a bold move to Florida.
That move paid off in more ways than one.
Rob spent several years at Bonita Bay Country Club before landing at The Sanctuary Golf Club on Sanibel Island, where he’s heading into his sixth season as Director of Outside Operations.
“It’s awesome, moving to Florida was the smartest thing I ever did in my life,” Rob said. I got out of the pro shop, took over Outside Ops at Sanctuary Golf Club on Sanibel Island. It’s great being outside, I still serve the game as a golf professional, just in a completely different role and It’s one that I just thrive in.”
Comedian Rob Churchill in Boston
From Tee Times to Punchlines
In 2018, at age 40, Rob tried something new, stand-up comedy. On a whim, he signed up for an open mic night. Threw a few jokes together, got up there, and somehow walked off with second place. That was it he was hooked.
Since then, he’s toured nationally, sharing stages with A List comedy heavyweights like Ron White, Nick DiPaolo, and T.J. Miller. He’s also built his own comedy community: Calusa Comedy Club, an intimate venue on Sanibel Island and the heart of his production company, Calusa Comedy Productions.
“It’s a place to laugh and giggle in paradise,” Rob says. “We’ve had national touring acts, local comics, it’s all about connection. Laughter brings people together.”
Love, Loss and Legacy
On May 23, 2025 Rob lost his mother Christine, a dedicated nurse of over 40 years and a beloved presence in Quincy. She passed peacefully in her home after a 2.5-year battle with pancreatic cancer, surrounded by family, held in love. 100’s of well-wishers, family and friends came out to Sweeney Funeral Home to pay respects.
“The resilience, courage and strength she showed every day is something I’ll try to emulate for the rest of my life,” Rob says. “A piece of me will forever be missing.”
Just five days after her passing, Rob was back on stage. “That’s what my mom would have wanted. I know she wouldn’t want me to sit around. I know she doesn’t want me to be sad. For me to keep going. Make people laugh. Live loud and love big.”
He honors her legacy in more ways than one. Christine asked if in lieu of flowers, donations be made to Valerie’s House, a nonprofit run by Rob’s wife Angela. A grief support network for children and families coping with loss. Angela, a former news reporter, started Valerie’s house 8 years ago in Ft. Myers, Florida in honor of her mother Valerie who passed away in a car accident when she was just 10 years old.
“My wife is the most amazing woman I’ve ever met besides my mom,” Rob says. “Valerie’s House is doing life changing work, and I’m proud to support it.”
Click to Listen! WATD SPORTS AUDIO EXTRA: Rob Churchill Comedy and Family
Family First
Rob’s parents, Richard and Christine, were married for 50 years. His father fought in the Army during the Vietnam War. From there he served 20 years as a Marine and lastly a Quincy police officer with 27 years on the beat.
“He is one of the good guys,” Rob says. “My friends were always relieved when he showed up on a call when they were about to get into trouble, they knew they’d be okay.”
Golf still brings them together. “My mom didn’t play, but she knew how much the game meant to us. It was our glue. We’d go out and we’d get to spend time together, she loved that she loved that we got to do that, probably didn’t love how much we swore out on the course though!”
Rob is the oldest of three siblings. His sister, Sara, and brother, Richard, still live in Quincy.
Richard and Rob Churchill golfing at Pebble Beach in California
Churchill’s Second Act
Now 47, Rob Churchill is a man of many talents. He’s funny, heartfelt, and uniquely positioned at the intersection of sports, entertainment, and emotional resilience.
Whether it’s outside ops or tight five sets, Rob’s still doing it his way. This life? He didn’t just dream it up, he earned it, one swing and one laugh at a time.
Catch Rob Churchill live at Calusa Comedy Club on Sanibel Island or follow him on tour via @CalusaComedy Want to support Valerie’s House? Visit Valerie’s House
Sports Reporter Liza “Goldie” Churchill has been covering the golf beat for 95.9 WATD Sports since 2009. She’s a member of the Golf Writers Association of America and Association of Women in Sports Media.