Jack Caldwell Covers The Super Bowl

WWPT-FM — Staples High School’s award-winning radio station — produces great sports broadcasters as regularly as the New England Patriots used to win Super Bowls.

Jack Caldwell is the latest in that long and storied line. He’s smooth and steady. He prepares well. He knows his stuff. He’s good.

In addition to play-by-play, he does music and news. This year’s, he’s WWPT’s executive director. In his spare time, he’s broadcast director for the student newspaper Inklings.

His sports cred comes naturally. He comes from a long line of baseball fans. His grandmother told stories of listening to Vin Scully call Brooklyn Dodgers games; together, Jack and she discussed their favorite (and least favorite) announcers.

His father Chris is in sports marketing. He’s worked at every Super Bowl since XXXIV (that was in 2000, for you non-sports fans). So Jack and his dad have never had a chance to watch the big game together.

This year — as an early graduation present — Chris took Jack to Minnesota. He tried to get 2 tickets, but wasn’t sure if he could. They decided they’d watch Super Bowl LII together — even if that meant doing it at the hotel.

Sunday morning, Jack’s dad surprised him with 2 tickets.

Jack Caldwell and his dad at the Super Bowl.

Before the game on Sunday morning, Jack attended an event with broadcast personalities Trey Wingo, Tony Romo and Cris Carter. After, he chatted with them. When he said he was an aspiring broadcaster, Romo and Carter posed for this photo with him.

You’ll notice Jack’s wearing his WWPT logowear. Fans were allowed to do “mock” broadcasts on a set at US Bank Stadium. This was Jack’s first broadcast ever with his father.

I’m not a betting guy, but I bet Jack’s broadcast was better than any other fan who stepped into that booth.

It was a working weekend for Jack. He watched and learned as much as he could.

WNBC reporter Bruce Beck — an avid WWPT-FM supporter and mentor — allowed Jack to shadow him as he worked.

On Saturday — despite 6 inches of snow — he explored many media sites, and visited the ESPN set. The Lombardi Trophy was there. Well, an ice sculpture replica of it, anyway.

As for the game: Jack’s a Jets fan; his dad likes the Lions. Going in, they were “reluctantly” rooting for the Eagles. But when the training scene from “Rocky II” was shown as Philadelphia’s hype video, they were won over for the night.

It was a fantastic weekend. There’s nothing like sharing the Super Bowl with your dad.

Especially when you can take a photo like this, moments after the final whistle.

BONUS STORY ON JACK CALDWELLAs a sophomore, knee surgery forced Jack into a wheelchair for 6  months.

His favorite sport to call is ice hockey. When the Wreckers made the state semifinals — at the “Yale Whale” arena — he worried he could not get to the press box.

WWPT friends and family helped him up, then helped him set up equipment. He called the game — an overtime Staples win.

That support meant a lot to Jack. It meant even more when that broadcast earned him a 2nd-place award in the national John Drury radio competition.

Last year, Jack and the station won honors in every Drury category they entered.

WWPT-FM faculty advisor Geno Heiter (left) and student broadcasters jump for joy after earning 12 John Drury Awards.

The Super Bowl — seeing media row and shadowing Bruce Beck — was a fantastic experience. Jack learned a lot about “real world media,” and looks forward to sharing that knowledge with everyone involved in media at Staples.

For his senior internship at May, he’ll work on the “Anna & Raven Show” on Star 99.9 FM. He hopes to study broadcast journalism in college (he will hear from schools in March).

After that — well, like other WWPT sportscasters, the sky’s the limit.

The Super Bowl was an important weekend, Jack says.

“I got to have a real fan experience,” he notes. “So if I begin to cover events for real in broadcasting, now they won’t seem as daunting.”

13 responses to “Jack Caldwell Covers The Super Bowl

  1. Elizabeth Kline

    What an amazing article for a really wonderful young man! You have persisted in following your dreams even with quite a few medical bumps along the way. So incredibly proud of all you’ve accomplished and all that is to come. I love how they included your Gram! XO

  2. Patricia Daly

    Great article featuring a unique and talented young man. It has been exciting watching Jack develop his broadcast skills, with extraordinary experiences along the way, this one in particular. Can’t wait to see where life takes him in the future. Gotta love this kid!

  3. Jennifer Levinson

    Great job Jack! I know we are going to hear a lot more from you in the coming years!!!!

  4. Way to go, Jack! Awesome article. You have a bright future ahead of you. Can your dad work his magic and get three Super Bowl tickets next year?

  5. Chris Caldwell


  6. Maureen Davis

    Great article about a great young man! Jack’s work ethic and commitment to pursuing his passion is impressive. Not only is he a hard worker, he is also a kind and thoughtful person. He is a wonderful role model for my kids! So proud of you, Jack!

  7. Wow! Way to go Jack Caldwell! I have heard him and he is the REAL deal! Can’t wait to see what Jack will be doing in the coming years. Hope we will get to hear him on the national level-no doubt. Keep up the excellent and professional work Jack!

  8. Great story. Thanks for sharing!

  9. I have heard Jack do both sports and music broadcasts on Wrecker Radio and, as someone commented above, Jack is indeed the real deal. He had an amazing show at the end of the last school year on the 50th anniversary of the release of “Sgt. Pepper’s”–I couldn’t get over that it was a high school junior doing this. He has a very promising future in sports or music.

  10. Fabulous article about Jack Caldwell. He is one of my son’s closest friends. He is not only a talented radio broadcaster, but a caring and kind friend. We are so proud of you Jack!!!!

  11. Lynne Caldwell

    I am so proud of all your accomplishments, Jack…and I know Pops is too! We’re happy that you love what you’re doing and we know there is a great future ahead of you. Love, Mimi

  12. Dr. Gregory Payne

    So proud of your accomplishments. Look forward to seeing you at Emerson.

  13. We are always so proud of your accomplishments. You are hard working and it shows in your broadcasts. You have a wonderful future ahead and we will be listening. Way to go Jack!!