Capt. Thomas J. Cain III
Claim this Obituary
Gloucester - Captain Thomas Joseph Cain III, passed away peacefully Sunday morning, October 27, surrounded by his three children, Michael Cain, Hannah Cain and Heather Cain.
In addition to this three children, all of whom were born and raised in Gloucester, Thomas is survived by his mother, Beverly Cain of Gloucester; younger brother, Timothy Cain of Essex; younger sister, Tracey O'Donavan of East Sandwich; former wife, Holly Cain of Gloucester; two granddaughters, Violet and Kingsley Cain of Gloucester; and grandson, Raith Newton of Revere. He was predeceased by his father, Thomas Joseph Cain Jr. of Gloucester.
Thomas "Caino" Cain was born and raised in Gloucester. He was a man of courage, humor and integrity. He was tough as nails, approaching life head on and accepting any challenge, no matter the size. Caino had the warmest heart imaginable, was full of wisdom and was sincere and honest. He was a generous person, someone who was quick to literally give the shirt off of his back. He was a proud father, grandfather and Gloucesterman. He was a well respected Fisherman and Captain. He fished off of numerous commercial vessels including the Odessa, the Middle Bank, the Kristen Lee and the Winner 3. Some of his all-time favorite crewmates included Capt. Bob Anderson and Capt. Billy Crossen, both of whom he was predeceased by as well as Capt. Brett Clayton, who he is survived by.
Caino lived for his three kids and three grandchildren. They were his world and he could not have been more proud of them. He was adamant that they laugh each day, keep each other close and do whatever made them happy in life, something his children say they will live by forever.
He loved attending his kids' sporting events from Riverdale Rocket days to collegiate level games. He also had a blast attending his son's Mariner baseball games and coaching AAU Freedom baseball alongside his son. He made it a point to embrace his children's coaches and teammates as family. He was proud and grateful for his and his children's circle of friends, whom he trusted and loved dearly.
He loved music, cooking and crossword puzzles. He loved getting a fire going in the wood stove. He was a weather guru and enjoyed all parts of nature, especially the ocean, stars and sunsets. He watched the sunset each night at Lanes Cove with his family and friends, always in his favorite wardrobe items, Crocs and a flannel. Caino had a colorful vocabulary and was a straight shooter, telling you how it was, no matter what it was. He was loved beyond measure and will be missed like no other. There will never ever be another soul like Caino.

Visiting hours in his honor will be held on Tuesday, November 5th from 4 to 7 p.m. in the Greely Funeral Home, 212 Washington Street, Gloucester. A Celebration of Life will be held in the summer of 2020.
As he believed in giving back and investing in the youth from his community, his children have started a scholarship foundation in his name: The Caino Legacy Foundation. This scholarship will be awarded annually to a graduating senior from Gloucester High School who is pursuing a certificate program, trade school or college/university degree. The scholarship will be awarded to a student who simply deserves it. In lieu of flowers, donations to his scholarship foundation would be appreciated. Please send donations to Cape Ann Savings Bank, 38 Rogers Street in Gloucester, MA 01930. Please make donations payable to Caino Legacy Foundation. Online contributions can be made at
For online condolences, please visit
Published on October 31, 2019


Plant a tree in memory
of Capt. Thomas
Plant a tree

Obituary published in


Print Guestbook

A place to share condolences and memories.
The guestbook expires on January 28, 2020.

Showing 10 of 18 posts

Francesca Combs
Nov 15, 2019
Michael, Heather, and Hannah, "Harry" as your Dad will always be known to me and me to him, was a special man. Your obituary is beautiful and so true. He was a straight shooter and just a great, great man. I am going to miss him no end. Sending much love to all of you. It's a huge loss to all of us and to Lanesville. He was always there when I needed him. So sad right now.
Donna Riley Mateus
Nov 11, 2019
Bunnie, Tim & Tracey,
Way too many memories to single out just one. Growing up on Hickory St, we were always getting into mischief. Discovering the woods, every nook and cranny, ding dong dash and working old man Cheves crazy, bombing thru the woods on his mini bike to crawling around the inside of the cove wall, our families were close and we were like family. So glad and happy that I got to see him at the cove the last time I came up to visit. Spread your wings and fly old man, I know I’ll see you on the other side. Out of pain and free at last. Much love Donna.
Nikki Barusso Kaloust
Nov 04, 2019
My handsome cousin! I looked up to you when I was growing up. You were “Clint Eastwood” cool. I loved being around you, Tim and Tracy, especially during the holidays! You always had the best smile and a devilish grin! I will miss you so very much. I wish I saw more of you these last few years. You are leaving an amazing legacy with your beautiful family! RIP cousin❤️
Gail Bellefleur
Nov 04, 2019
Amazing Arboricola was purchased for the family of Capt. Thomas J. Cain III by Gail Bellefleur.  Send flowers
Kim and Bill Eaton
Nov 04, 2019
I will treasure all the memories I have of you growing up, spending time at your house when our family went East . . . and those special times I spent with you down at the cove and kayaking . . . .Bill will always remember you taking him out on the boats, allowing him to be 2nd mate. You are loved "Tommy" and will be dearly missed!!!
Aurora Desmond
Nov 02, 2019
Lanseville lost one of the greats. I'm so sorry for your loss.
Beth Simpson
Nov 02, 2019
Bev and family,
I am so terribly sorry for such a loss. Please accept my heartfelt condolences. Thoughts and prayers are with you and your family at this time.
Margie Burns Sinagra
Nov 01, 2019
So sorry to here about Tom I remember him giving us rides to the high school hockey games before we could drive and all the times I would talk to him when he was my sisters landlord and I will never forget when I went to my parents one year in New Years and he was in the kitchen making his delicious sauce after coming in from fishing with my Dad Thinking If you all all sending prayers to all of you Margie
Sharon Lilienthal-Cyr
Nov 01, 2019
I cherish the memories of a wonderful human being and send my heartfelt sympathies for your tremendous loss.
My thoughts and prayers are with you all during this time.
Wesley Thibodeau
Oct 31, 2019
To the Cain family, my heartfelt condolences to you all. I knew Caino in the 90's, when I was a chef at the Halibut Point Restaurant and he always had a smile and a hearty laugh for everyone he met and everyone he talked to. He was a good man and I know he will be missed by all who knew him. Peace to you all...
Skye foote
Oct 31, 2019
You were so happy to see me on my boat this summer 🥰 your were always wanting to hear how I was doing in school. You were a special man I never will forget all the advice you gave me❤️