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October 28, 2026

Jack in the Media: Five Veterans, One Table, and the Question Everyone Should Ask

Jack joins the Cumberland Unfiltered Veterans Day panel, his third appearance on the show this year.

Every November, the Cumberland Unfiltered podcast hands its table over to veterans. This year’s Veterans Day show brought together five men with very different paths through the military, and Jack was proud to be one of them.

Around the table:

  • Vic Mellor, a former Marine explosive-detection dog handler who worked details for the President, now running for Congress.
  • Nicholas Credle, a 10-year Army veteran and retired captain who once coached track at the West Point prep school.
  • Luke Bonin, a 2nd Ranger Battalion veteran who later served 14 years in the Rhode Island Army National Guard and graduated first in his Massachusetts State Police Academy class.
  • George Huddleston, a 35-year Army veteran: MP, infantryman, drill sergeant, Special Forces, with deployments from Bosnia to Iraq and Afghanistan.
  • Jack Flynn, who served in the Rhode Island Army National Guard from 1992 to 2019, deployed to Afghanistan, and worked alongside the Afghan National Army.

Jack opens the show, and over the next two hours (with plenty of laughs) the conversation covers combat, college costs, VA benefits, drones and what Veterans Day really means.

“What did you do?”

The moment that stuck with everyone came from a simple idea Jack shared.

Most people, when they learn someone served, say “Thank you for your service.” Veterans appreciate it. But Jack’s point was that there is a better next step: ask “What did you do?”

He told the story of standing on stage at a company event for American Warrior Initiative, which raises service dogs for veterans. Next to him was a quiet older man who had helped make the dog program happen. Jack asked him what he had done in the military. The answer: he had been a tunnel rat in Vietnam, three tours.

Jack sat down on the stage with him and his dog, and for five minutes the man shared a piece of his life. “I learned a lifetime worth of information in that five-minute conversation,” Jack said. “All it took was for me to say, what did you do?”

The other panelists jumped in with their own versions. Luke told of a restaurant in Maine where veterans sign a giant American flag, and how spotting his neighbor’s name on it led to hours of stories from a Vietnam radio operator who lived right next door. It all started with the same question.

That’s Jack’s challenge to anyone who wants to honor a veteran this November: don’t stop at thank you. Ask what they did, and then listen.

Giving the VA credit where it’s due

Jack also pushed back on a common story: that the VA doesn’t take care of veterans.

At a Run to Home Base event at Fenway Park, a race he has run more than ten times, he heard a speaker tell the crowd that the VA doesn’t do enough. That bothered him, because it hasn’t been his experience. “Most veterans, if they self-advocate, have a very good experience with the VA,” he said.

He had a real example. When Jack needed a hip replacement, he sent a message through the VA phone app. In less than 24 hours, VA orthopedics in Boston called back, and within about 40 days he was seeing one of the best surgeons around.

The panel agreed the system isn’t perfect. Vic shared a hard story about his uncle, a Vietnam veteran who nearly fell through the cracks. But the theme kept coming back: the benefits are there, and veterans who speak up for themselves get the most from them.

Iron sharpens iron

Underneath the jokes (and there were a lot of them), the conversation kept circling back to the values the military teaches: selfless service, accountability, competing to be better, and taking care of the people beside you. Jack summed up the spirit with a phrase from rugby: iron sharpens iron.

Watch the full episode

The full Veterans Day show is on the Cumberland Unfiltered YouTube channel. It runs about two and a half hours, so grab a drink and settle in.

Watch on YouTube · Cumberland Unfiltered channel

This post is part of “Jack in the Media,” where we share the podcasts, interviews and conversations Jack takes part in.

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