Pedaling his legs as he holds onto hand rails, Whidbey Island celebrity Jim Freeman shows off the railroad caboose he calls home in 2016 in Freeland. Freeman, 74, known as the Conductor of Fun, died June 19. (Andy Bronson / The Herald)

Pedaling his legs as he holds onto hand rails, Whidbey Island celebrity Jim Freeman shows off the railroad caboose he calls home in 2016 in Freeland. Freeman, 74, known as the Conductor of Fun, died June 19. (Andy Bronson / The Herald)

‘End of an era’ with death of Whidbey celebrity Jim Freeman

Freeman, 74, lived in a train caboose and was the Conductor of Fun. “His sneakers will never be filled.”

WHIDBEY ISLAND — For the first time ever, the Conductor of Fun is making people sad.

Jim Freeman died on June 19, a week before his birthday. He was 74.98.

Freeman, a Marine Corps veteran and law school graduate, lived in a red caboose parked in the woods of Freeland. The Loose Caboose, he called it. His email address was

If you met him, you’d never forget him. They just don’t make characters like him anymore.

“The end of an era,” a social media post sums his passing.

Tall, lanky with long wispy hair, white tennis shoes, a flip phone and a flip sense of humor, the guy had a toothy smile that took over half of his elastic face.

We visited Freeman in 2016 in the Loose Caboose, a 1928 Milwaukee Red railroad car tucked on 6 acres off Newman Road. Reporter Ben Watanabe, a former South Whidbey Record writer, said Freeman was the best story on the island.

Ben was right.

Herald photographer Andy Bronson and I were wowed by his life and the caboose.

Freeman showed us around his 625-square-foot man cave-oose with an arcade pinball machine, portrait of Roy Rogers over the bed and plastic Disney cartoon party banner for a bathroom door.

Under twinkling holiday lights strung on the ceiling, he sang along with Marvin Gaye crooning “How Sweet It Is” on a music video on a small TV.

In his fridge: frozen White Castle cheeseburgers, Darigold chocolate milk and Gates Extra Hot Bar-B-Q sauce, shipped from Kansas City.

I was ready to shuck my mundane existence and move into the Loose Caboose.

Jim Freeman stands inside the 1928 Milwaukee Road railroad car caboose he called home in 2016 in Freeland, Whidbey Island. (Andy Bronson / The Herald)

Jim Freeman stands inside the 1928 Milwaukee Road railroad car caboose he called home in 2016 in Freeland, Whidbey Island. (Andy Bronson / The Herald)

Freeman makes you realize you have the power to live however you want, something most of us forget.

Instead of making big bucks as an L.A. lawyer, Freeman moved to Whidbey where he led parades, festivals and fundraisers. Instead of a three-piece suit, he wore mismatched plaid, party hats and waved pompoms. He curated the gag prizes he gave to everyone at poetry slams.

“He was the voice of the community at so many events,” said Brook Willeford, co-owner of The Clyde Theatre in Langley.

“You could always count on a good time with Jim,” Whidbey artist and musician Sarah Dial Primrose said. “You know how sometimes you see somebody in the grocery store and you just want to hide because you’re like, ‘No, I don’t want to talk to them.’ You always wanted to see Jim. He always had something really good to say.”

Freeman wrote a witty column “On Track” for the Whidbey Weekly. A play was performed based on a column. Mukilteo Coffee Roasters named a coffee blend after him.

He was dealing with medical issues at the time of his death.

“He was always very helpful to others, but never would accept help for himself,” his longtime friend Dave Draper said. “He’d be the last guy who wanted somebody to do a celebration of life for him.”

Here’s a condensed bio of Freeman’s pre-Whidbey life, as told in the 2016 Herald story:

“When I started practicing law I realized, this is not fun, there’s no happiness, there’s not a lot of honesty,” Freeman said.

There were some perks: “I once had lunch with Judge John Sirica during the Watergate trial.”

Then along came Willie.

“A college buddy said Willie Nelson’s manager was looking for a fan club president. I said, ‘Hook me up with him.’ That was 1975. I realized I wanted to be in the entertainment business, not the courtroom,” he said.

“I worked with Willie as his PR guy when not many knew him. After smoking pot on top of the White House, he didn’t need me anymore. We parted ways and everything was cool.”

Freeman started doing TV commercials in L.A., such as one for a Seattle area bartending academy: “I was the guy who’d throw all the stuff off the desk, saying, ‘You want to be your own boss? Want to have your own hours?’”

He did improv and got bit parts in films, but he yearned for more.

“I was in L.A. at a bar on a Friday wondering, what am I going to do with my life? A guy was staring at me. I said, ‘Want to buy me a drink, want to kiss me, what’s the big deal here?’ He said, ‘I’ve seen you somewhere … You’re the bartending guy!’ He said he was from Seattle. I said, ‘If I could live anywhere in the area but not in Seattle, where would you go?’ He said ‘Whidbey Island.’”

Freeman moved to a Whidbey beach house in 1983 and initially commuted to L.A. for gigs. A year later, the caboose became his home.

He had a bigger fan club than Willie Nelson.

“His sneakers will never be filled,” a Facebook post says.

Andrea Brown: 425-339-3443;; Twitter: @reporterbrown.

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