On Friday in Toronto, Jacobs will be given a ring smaller in size but at least equal, if not greater in significance -- one that will mark his induction into the Hockey Hall of Fame as a builder (the formal ceremony will be Monday).
Bruins chief executive officer Charlie Jacobs, the youngest of Jeremy and Margaret Jacobs' six children, laughed as he shared this:
"My mother asked my father, 'Now that you'll be getting a Hockey Hall of Fame ring, what are you going to wear? Two rings?' " he said. "And my father said, 'No, no… the Hall of Fame ring is going to be on my finger.' I think that puts things into perspective."
Jeremy Jacobs, 77, has been a hugely influential figure in NHL boardrooms for decades, the chairman of the Board of Governors since 2007. He has served on the League's Audit, Finance and Executive committees since 1979.
A towering figure in sports, business and philanthropy, Jacobs is the sixth member of the Bruins family to be elected to the Hall of Fame as a builder. He follows, chronologically: Charles F. Adams, the Bruins founder, inducted in 1960; owner Walter A. Brown, 1962; owner Weston W. Adams, 1972; Harry Sinden, the famed Bruins president, general manager and coach, 1983; and coach Pat Burns, 2014.
"This was a total surprise," Jacobs said when his election to the Hall of Fame was announced June 26. "I'm humbled and very appreciative."
The game, he said at the time, has been in his blood forever.
"My family was involved in hockey from the day I was born, when they owned the old Buffalo Bisons [of the American Hockey League] many, many years ago," he said. "It's been part of my life and this type of recognition was unexpected but very, very much appreciated."
In 41 NHL seasons since Jacobs purchased the Bruins in August 1975, his team has qualified for the Stanley Cup Playoffs 34 times. Boston defeated the Vancouver Canucks in 2011 to win its first championship since 1972, having advanced to the Stanley Cup Final five times between those titles.
Ownership of the Bruins and TD Garden, their home arena that opened in 1995, is a sliver of Jacobs' life. For more than 40 years, the Bruins owner and chairman has been chairman of Delaware North, a global giant in hospitality and food service that annually serves half a billion people on four continents. Founded in 1915 by Jacobs' father, Louis, and two uncles, who modestly sold snacks at movie theaters, the company has annual revenues of about $3 billion.
In 2003, Jacobs and his family established the Boston Bruins Foundation, which has raised more than $28 million to improve the quality of life of New England children. The Buffalo, New York, native's wide-ranging philanthropic efforts and work in sports earned him induction in the Greater Buffalo Sports Hall of Fame in 2006 and the Hockey Legacy Award from the Sports Museum in Boston in 2012. He also was awarded the prestigious Lester Patrick Trophy from the NHL and USA Hockey in 2015, honoring his contribution to hockey in the United States, and was enshrined a year in the Massachusetts Hockey Hall of Fame.
A graduate of the University at Buffalo's School of Management and the Harvard School of Business Advanced Management Program, Jacobs has been awarded honorary doctorates from four universities. His family's $50 million in donations to the University at Buffalo was recognized by the institution, which named its medical school the Jacobs School of Medicine and Biomedical Sciences.
Through all of this, Jacobs would never deny that his heart beats to the rhythm of his Bruins. His Hockey Hall of Fame election, Charlie Jacobs said, means the world to him.
"When he first got the call (from Hall of Fame chairman Lanny McDonald), there was a lot of chatter among siblings, of course, my parents, with aunts and uncles, et cetera, calling and congratulating," he said. "I don't think it had sunk in then with my dad, or what it means to him today and what it will mean to him come his induction. …
"The Bruins are an emotional investment for my father, absolutely. There's no doubt. He's very much emotionally tied to family, business, and the business of the family. That's where I think the Boston Bruins intersect. We pride ourselves in terms of integrity and ethics and family. My dad is very much a family man. … The Bruins are his way of connecting with his kids, his  grandkids and his [two] great-grandkids, to sit down and enjoy a game and discuss our love and passion for the sport."
If any of the Jacobs grandchildren, young kids often attracted by superstars and flashy jerseys, cheer for a team other than the Bruins, they don't do so loudly.
"They wouldn't do it in front of me and certainly not in front of The Chairman," Charlie Jacobs said. "I'd kick 'em out if they did. That message was sent long, long ago. …
"What might have been a financial investment for my father has really become more of a passion. He doesn't look upon the Bruins as anything other than a public trust he holds to steward and hopefully -- and I hope he thinks this way -- for future generations of his family to continue that legacy."
Johnny Bucyk, the Hall of Fame forward who with Bobby Orr is the face of the Bruins for many, has been impressed by Jacobs' desire to listen and to learn.
"I don't think he fully knew what to expect when he bought the team in 1975," said Bucyk, a member of the Bruins' 1970 and 1972 Stanley Cup champions who has worked for three ownership regimes during his 61 years with Boston. "But he understands the organization and how Boston and the different areas around the town feel about hockey. The Bruins are the No. 1 priority to many people and he realizes that. …
"He's going to be very proud and happy when he goes into the Hall of Fame, as we are as players. To me, it's secondary only to winning the Stanley Cup. To get into the Hall, you must have been good and you must have done your job well. It's a great honor."
Charlie Jacobs was 4 when his father bought the Bruins. He jokes that the hockey team is, in fact, his father's seventh child.
"My mom and dad bought a home that year (1975) in East Aurora, New York, a suburb of Buffalo," he said. "It was a big year for my dad. He was a young man, just 35 years old. We moved to this new home and my first memories of it were of us gathered around TV 38 [Boston's WSBK], watching Bruins hockey off a giant satellite with broadcasters Fred Cusick and Johnny Peirson.
"I remember the addition of a new child -- I was the sixth and the Bruins were the seventh because they came with the new house, that's how I look at it."
On 2017 induction weekend, with a huge family contingent on hand, Jacobs will return to the Hall of Fame and spend more time enjoying its salute to many enshrined Bruins legends.
As stately as the Hall of Fame might be, Jacobs and his family have seen it in a less serious light, too.
"We had a Bruins function at the Hall years ago," Charlie Jacobs said, his father having figuratively sat at the head of the table. "It is very humbling to see all that history and grandeur. I remember Harry (Sinden) organized it, and it was one of my first introductions to some of the rituals of team building.
"One of our younger players sneaked the butter from the tray and managed to weave his way under the tables and dab it on one of our coaches' shoes, or maybe it was Harry's, then sneak all the way back and get into his chair. There we were, in the Hall of Fame, thinking, 'Everybody check your shoes and see who he got.' "
More than likely, Jeremy Jacobs will remember that playful night when he walks up to deliver his induction speech, just as he'll again enjoy every Hall of Fame exhibit that highlights Bruins players and builders.
"And then there's that moment when you step into the vault where they keep the (original) Stanley Cup," Charlie Jacobs said. "That has some gravity to it, to see the living history of the Stanley Cup in the shrine."
Jeremy Jacobs' offices are not without their own priceless souvenirs of Bruins hockey covering his four-plus decades as team owner. He cherishes a photo that's seldom been seen beyond the family, one offered by Charlie for this story: 24 members of the Jacobs clan sitting before the Bruins' 2011-12 home opener, the Stanley Cup gleaming among them.
"I don't think my dad would find this disparaging for me to say," Charlie Jacobs said. "For a kid from Buffalo who has gone on to do what he's done, to be very, very active in the Buffalo and Boston communities, and now to think that he'll be in the hallowed halls in Toronto, forever enshrined. … I won't speak for him, I think he'll affirm this when the time comes, but it's one of his greatest accolades."