‘A joy to be around’

Jack Shea is being remembered for his contributions to The Times and Martha's Vineyard.

Jack Shea died on Sunday and if you knew him you’re no doubt feeling a tremendous sense of loss at reading those words.

Jack was a larger-than-life character who immediately put his friends at ease with his wry sense of humor. He loved telling stories and did it well in his role as a freelance writer for The Martha’s Vineyard Times.

Jack was in Florida at the time of his passing helping a longtime friend and golf buddy, Ron Kasmouski, who was suffering from an illness. No surprise to anyone who knows Jack. While he was there he went into cardiac arrest five days ago and died in the hospital Sunday morning, his daughter, Kathryn Shea-Stocking, said. 

Jack hasn’t lived on Martha’s Vineyard in several years, but regular readers of The Times wouldn’t know that. He was still writing his book reviews and in the fall covered the Martha’s Vineyard Regional High School football team through regular conversations with coach Donald Herman.

“Anyone who had the privilege of knowing Jack, knew what a kind, decent, honest man that he was and a joy to be around,” Debbie Grant wrote in an email to The Times.

Grant and her husband, Mike Cassidy, were close friends of Jack and he lived with them for a time at their Edgartown home.

“I met him playing golf and we kind of hit it off,” Cassidy told me. “We realized we had a lot in common. We became regular partners.”

Jack grew up in South Boston or as he would call it “Southie.” Cassidy grew up in Norwood. They were both Irishmen, but had more than that in common. 

Jack was married 23 years and divorced. Cassidy was married 26 years and divorced. They both had three children — boy, girl, boy. Jack’s father died at Mass. General Hospital in 1989, so did Cassidy’s. Jack’s mother died at home in 1994, so did Cassidy’s. You get the picture. They could relate.

“We’re twins separated at birth,” Cassidy joked. “Brothers from different mothers.”

It went a step further for the two of them. Cassidy worked at a nursing home in Norwood where he cooked and delivered meals. Turns out that’s where Jack’s grandparents were until they died at 105 and 103 years old a couple of months apart while Cassidy worked there. Jack was a frequent visitor so it’s likely their lives crossed paths before they met at the Edgartown Golf Club.

“We became the closest friends,” Cassidy said. 

Jack was a friend you could count on. When Cassidy’s daughter was diagnosed with lymphoma at 7 years old, Cassidy told her he would shave his head in solidarity when she started her treatments at the Jimmy Fund clinic. But when the day came, his daughter told him it wasn’t necessary. “I was never so relieved in all my life,” Cassidy said. That is, until a text came in, and there were the freshly shaved heads of Jack Shea and Jim Kligensmith staring back at him.

“Oh man, I’ve gotta go through with it now. I can’t go back to the Island with a head of hair,” he said.

Jack would keep that signature look throughout the rest of his life. Bald head, a white beard and the biggest smile.

Jack had a long and successful career in the newspaper industry, which included the Patriot Ledger newspaper on the South Shore.

In his “retirement,” Jack enjoyed writing and storytelling for The Times. 

MVRHS football coach Donald Herman, who recently retired (Jack broke that story), called Jack the consummate professional. “He just always made himself available. He loved to add throwback quotes and thoughts from his generation into the conversation,” Herman said. 

Jack was a reporter he could trust. “I was able to speak my mind and he did a good job of making me sound good,” Coach Herman said. “He’s definitely going to be missed. Whenever I had something I thought needed to be in the paper, he’s the first person I contacted.”

Nelson Sigelman, the former editor of The Times, fondly remembered his time working with Jack.

“I met Jack Shea when I was the managing editor of this newspaper soon after he arrived on the Island. Had I been a casting director, I would have hired him to play the role of an old-school freelance newspaperman who knew his trade. Jack looked and acted the part. He understood what it was to experience and report on hard times. It was etched into the lines on his face,” Sigelman wrote in an email. “He might have looked intimidating, but for a twinkle in his eye that let you know, ‘Hey, don’t worry about a thing. It’s all good.’”

Jack was an old-school journalist.

“Tweets and texts are now a common form of communication. Jack preferred to talk to people, and he was good at it,” Sigelman recalled. “The best reporters know how to make people feel comfortable. Jack reported on the full menu of Island life, but he had a flair for sports and features. Describing the women’s softball opener in June 2014, Jack picked up on a key element of an Island spring: ‘Winter rust was not apparent in the season openers though outfield play turned problematic late in the game when several seemingly catchable fly balls disappeared into the misty fog and came to rest untouched.’

“Goodbye Jack.”

Connie Berry, Times features editor, recalled her interactions with Jack. “Jack always called me ‘kid,’ a welcome greeting when you’re 60 years old. He wrote hands-down the best book reviews ever. If there was a book that needed a deeper dive, it was Jack I would turn to. Kate Feiffer and I just had a conversation on Friday, talking about which books Jack would review before the Times’ annual Islanders Write event. ‘We’ve gotta have Jack do it,’ we said. I’ll miss his humor, his wisdom, and that twinkle he had like he knew what you were going to say before you said it.”

With his departure from the Island a couple of years ago, Jack’s visits to the newsroom became less frequent. But he did stop by last summer while he was on-Island for a wedding. It was a welcome interruption to the day.

His text message attaboys after a Times award or a big scoop were always welcomed, too. He was never short on story ideas either. During the last election cycle, he pitched an op-ed that I rejected because it lacked a Vineyard connection. When someone at CNN wrote something similar to what he predicted, he was quick to pounce. 

“Why are you telling me this, you ask?” Jack wrote. “Well, so you can really process the fact that you have an analyst with 50 years local, state, and national political reporting experience who knows what the [expletive] he’s talking about.”

I know, Jack. I know. And now you’re gone. A huge loss for me and every other life you touched during your 79 years.

His daughter, Kathryn, is still working on arrangements, but she said at some point his life will be celebrated on the Island he loved. He is survived by Kathryn and his two sons, Pete and Matt, both of Scituate, as well as seven grandchildren.

“He was just so special to us,” Cassidy said.


  1. Such sad news. They broke the mold when they made Jack. What an amazing soul he was. He cared so much about the young men and women who played high school sports – it was inspirational. I feel lucky to have known him. May he Rest In Peace and find comfort knowing how many lives he impacted with his grace.

  2. As an author living on the Island, I was fortunate to have Jack review several of my books. I learned from his reviews how to be a better writer, Thank you, Jack.

  3. Such sad news. Jack was a talented writer and always interesting to talk to. It was a privilege to work with him and to know him. He will be much missed!

  4. A newspaperman of the old school, he took stories that others might have dismissed as “small” or “insignificant” and — through his meticulous reporting and vivid writing — showed readers that they were anything but. Rest well, Jack . . . you will be missed.

  5. In january jack called me to review my recent book, his enthusiasm and curiosity were wonderful and the story he wrote was great. a loss to the MV times and us all.

  6. I was and am very sad to say goodbye to a good friend. We had many laughs together and shared various life trials that we would help each other through. It is a great honor to have known Jack, I last saw him briefly a couple of years ago on the island, a coffee, and a few laughs.
    In 2007 the Martha’s Vineyard Rotary Club which I am a member went to Peru and delivered Wheel Chairs to several communities around Lima, and up and down the coast. Jack asked for some pictures, took me to lunch, and asked questions, there was a full-page story I think in the Gazette. All about helping other people, which Jack was all about.
    RIP my friend

  7. This is very sad news. I only crossed paths briefly with Jack in March, 2018 when he wrote a piece about a political documentary I created years ago but was presenting at Pathways. I so thoroughly enjoyed the old time political discourse.

    He was engaging, disarming and a treasure trove of knowledge and wisdom. He was someone I would have loved to just sit and have shared coffee and life tales with for hours. He intuitively understood the inherent nature of it all.

    Grateful for the crossing of paths. Wishing you peace on your journey.

  8. Its hard to believe that Jack’s heart ever “arrested,” because I can’t believe it ever stopped working. Jack’s essence was his big heart, his twinkle of humor no matter what, and his graceful and careful writing. He even managed to make me relax and trust him as a reporter — no mean feat. It’s shocking that he’s gone, and many many of us will miss him mightily.

  9. I had the pleasure of working with Jack at the MV Times, and enjoyed many great conversations with him, and of course, lots of laughs. It always brightened my day when I would run into him and his dog walking along Main Street in Vineyard Haven, and we’d stop for a chat about the latest Island goings-on. As other commenters have observed, he wrote wonderful book reviews that included keen observations and insights gleaned from personal experience, and they made me want to read every book he wrote about. I looked forward to reading his feature articles, which often expressed a poignancy for the people he wrote about that revealed his kind and thoughtful nature. I feel very lucky to have known him.

  10. I first met Jack at a sharks game 7 years ago he always went out of his way to say hi and talk baseball he was as true as they get.

  11. I met Jack briefly at a Girl’s High School Soccer game he was covering a few years ago. He introduced himself and asked who my daughter was and when I told him, he was quick to say “we love watching her play!” It warmed my heart, made me proud, and left me feeling like I was talking to an old family friend. Seems like that was just the kind of guy he was. Funny how life’s brief encounters can have such a wonderful impact. Thanks for that, Jack.

  12. A great voice has been silenced
    Jack was a great man and a great writer
    He will be missed around here
    RIP, brother

Comments are closed.