Goal Driven

On a June afternoon in 2001, fifteen thousand Boston Bruins fans filled City Hall Plaza to celebrate the NHL championship won four days earlier by…the Colorado Avalanche. Midway through the prior season, legendary Bruins defenseman Ray Bourque, who’d played in black and gold since Jimmy Carter was president, had requested a trade. A year later, Bourque helped Colorado win the NHL title that had eluded the Bruins since 1972, leading Boston Mayor Tom Menino to invite him back to town to celebrate.

Though that party—where Bruins fans toasted a Stanley Cup won by another team—represented a low point in the team’s history, it also coincided with the beginning of a new era for the organization. Not long before, Bruins owner Jeremy Jacobs had called his sons Lou and Jerry Jr. into his office. He told them that he’d been thinking about bringing his youngest son, Charlie, into the family business. Jacobs’s idea was that, rather than live and work in Buffalo with the rest of the family, Charlie would be based in Boston.

Although Lou and Jerry admit today to being a little jealous at the time that they were passed over for their younger brother, they acknowledge that the choice made a lot of sense. Charlie had ties to Boston—he’s an Eagle, after all—and a passion for hockey that bordered on an obsession. And after nearly making the US Olympic equestrian team in the 1990s, he also had the kind of competitive drive it would take to help restore the Bruins to greatness. Now the family just had to convince him to take the position.

After graduating from BC in 1994, Jacobs had taken a job in hockey not with the Bruins but with the Los Angeles Kings. A few years later, he moved on to start his own successful web publishing company in San Francisco. “I could’ve stayed in San Francisco and been very happy,” Jacobs recently recalled. But he had teared up from his couch while watching Bourque win that Stanley Cup. His heart was still with the Bruins.

After joining the franchise in 2001, Charlie Jacobs is today the Bruins’ CEO. Though there have been the inevitable ups and downs of professional sports, the team under his leadership has been quite a success, winning the NHL championship for the first time in nearly four decades in 2011, and making it back to the finals in both 2013 and 2019.

When I visited Jacobs recently in the thirty-one-story office tower that houses the team’s headquarters on the corner of Causeway Street and Legends Way, he was dressed casually in blue jeans, a button-down shirt, and sneakers. His rescue dog, Berry, slept in the corner. He spoke softly enough that you could be forgiven for forgetting that his family owned the place, or that Jacobs had a large part in the construction of the tower we were sitting in. When Jacobs’s father, Jeremy Jacobs, bought the Bruins in 1975 for $10 million, he recognized it as a business opportunity. With the transaction, his company, called Delaware North, had purchased a historic franchise with a committed fan base, plus control of the legendary Boston Garden, where both the Bruins and the Boston Celtics played. Delaware North was founded in 1915 by Jeremy Jacobs’s father and two uncles as a theater concession business. Over the decades, the business grew rapidly, selling hot dogs and beverages at ballparks and horse racing tracks, and eventually evolving into a multinational hospitality company.

Acquiring the Bruins may have made good business sense, but it brought with it all the challenges of running a team in a city known for its demanding fan base. Under Jacobs’s ownership, the Bruins continued to make the playoffs each year through 1996—part of an NHL-record streak of twenty-nine straight seasons. But when the run ended without a title, criticism grew for spending near the bottom of the league in player salaries despite being near the top in profits. Making matters worse, Jacobs was rarely seen in Boston, instead entrusting General Manager Harry Sinden to lead the team. In an unscientific 2001 ESPN fan poll of the worst owners in sports, Jacobs came in number one. “There was a website called, ‘Please Sell the Bruins,’” Charlie Jacobs recalled. “As if we didn’t care—or all we cared about was selling concessions, which is nonsense, absolute nonsense.” Charlie, after all, had been a Bruins fanatic for basically his entire life.

Growing up in Buffalo, Charlie Jacobs watched Bruins games via a massive satellite dish, running out to clear snow off it in the winters. While in college, he would attend games and sit next to Sinden, soaking up information. “It wasn’t like we would go to Bruins games and drink beers and laugh and have fun,” his friend Philip Richter recalled. “It was work.”

After graduation, Jacobs was determined to work in hockey, and to earn his way. “I wanted to go out and learn the game,” he said. So in 1994 he left Boston for LA, joining the Kings organization. The work was hardly glamorous. One of his early jobs, for instance, was listening to radio broadcasts to ensure the correct ads ran during games. “I literally worked in the basement,” he recalled.

His exposure to team videos eventually helped him to see the benefits of new internet technology, and then a business opportunity. In 1998 he cofounded the company Total Media Group, which helped businesses publish videos digitally and create an online presence. The company started in a garage and grew to a staff of thirty by 2001, when Jacobs left Total Media Group and moved east.

Jacobs’s first job with the Bruins was to observe. “Nobody said, ‘If you come here you can run the Bruins,’” he said. Instead, he’d sit inside the hockey operations department, watch the games, and continue learning from Sinden.

He lived in a hotel across from the team’s arena, and traded holidays with family for time on the road alongside team scouts at junior games, college contests, and world youth championships. “I got to travel a lot, which was difficult because I had young kids,” he said, “but also fun because we were doing it for the game.”

Even as Jacobs was developing the skills required to one day run the organization, however, the Bruins and the entire league struggled. Bruins attendance dropped each year from 1999 to 2003, bottoming out at twenty-first in the league. Meanwhile, in the five seasons from 1999 to 2004, the team had five different head coaches. Then, in 2004, NHL Commissioner Gary Bettman announced a lockout of players, part of a fight to create a salary cap.

Six weeks later, when Jacobs traveled to St. Louis to witness the Red Sox win their first World Series in eighty-six years, he couldn’t help but wonder when Bruins fans would enjoy a similar moment. He was thirty-three at the time, and a Stanley Cup hadn’t been raised in Boston since he was six months old. His first thought after waking up was often: How do we get back there? But at the close of 2004, the team seemed farther away than ever.

The 2004–2005 NHL season was ultimately canceled, the only time an entire major pro sports season has been lost in North America. As the league got ready to resume playing the following season, it was clear the Bruins had work to do when it came to reconnecting with fans. And it was Charlie who would lead that effort. He oversaw a marketing campaign that featured staffers interviewing fans and the creation of a series of TV spots featuring the actor Denis Leary with Bruins players. Jacobs also reintroduced sections of ten-dollar tickets for the first time since 1987.

Then, in November 2005, the Bruins traded their star captain Joe Thornton to the San Jose Sharks. The shocking move stunned Thornton, fans…and Charlie Jacobs. He was boarding a plane when his phone rang. It was the team’s then-GM Mike O’Connell.

“Hey, I just traded Joe,” O’Connell said.

“Can you undo it?” Jacobs asked him.

By the end of the season, O’Connell was out. Sinden, then team president, sat Jacobs down and said he ought to help pick the next GM. Jacobs was thirty-four at the time, a year younger than his father had been when he took over the Bruins, and though it would be another decade before he was formally named CEO, his growing influence in the organization was already unmistakable.

The Jacobs’ interests in the Bruins are vast and multifaceted. Owning an NHL franchise today means managing an arena (TD Garden is worth nearly $1 billion alone), running a media business (the Bruins control 20 percent of New England Sports Network), maintaining a brand so meaningful that countless locals have tattooed its logo onto their flesh, and overseeing a group of professional athletes plus everything they need to perform at their best. But as Jacobs explained it, they’re all interconnected.

Everything from new arena seats to an upgraded scoreboard are seen as elements that improve fan experience, drive business outcomes, and ultimately help the team win. When Jacobs began playing a larger team role in 2006, he focused first on players’ perceptions of the organization. “I felt like we needed to put more importance on making sure that this was a destination,” he said. “We should have players clamoring to play here.”

That process began with the pick for general manager, Peter Chiarelli, a former players’ agent who was working as an assistant GM for the Ottawa Senators. Chiarelli knew what athletes were looking for in their team. In his first offseason, the Bruins were able to sign two of the top free agents on the market, center Marc Savard and defenseman Zdeno Chára. In the draft, meanwhile, the team added important future pieces in Phil Kessel, Milan Lucic, and Brad Marchand. They also traded for Tuukka Rask, who would become a dominant goalie.

Jacobs was around the team’s facility nonstop, working to improve the locker rooms, the business areas, and the overall organizational culture. Taken together, the new talent and focus ignited a three-year run starting in 2008 that would have been unthinkable just a few years earlier. When the 2007–2008 season ended with a surprise playoff appearance, fan attendance the following September at the team’s preseason “State of the Bruins” town hall doubled. Jeremy Jacobs was there, too, reflecting Charlie’s encouragement that his dad make more appearances in town. The Bruins made the playoffs again the next season, managing to win a series, and did the same in 2010.

As the 2010–2011 season approached, the Bruins’ transformation seemed complete. The team was big, fast, and skilled. But maybe most significant for Jacobs, it was tough. “The Bruins came on the ice,” he recalled, “and they had a certain gravitas to them—a feel of, Hey listen, you better keep yourself in line or you’re gonna get something handed to you.”

Jacobs was hardly the only one excited. The team’s fourteen thousand season tickets sold out. “This is like a keg of TNT,” Jacobs said at the time. “Hopefully it explodes.”

It certainly did. That season, the Bruins made it to the Stanley Cup Finals for the first time since 1990. Facing the Vancouver Canucks, the Bruins got off to a difficult start, losing the first two games on the road. But then that toughness emerged, and from that point on, the Bruins dominated the series, winning four of the next five games to claim the team’s first championship since 1972.

The win was the culmination of a decade-long rebuild. “There’s no words to describe that feeling,” Jacobs said of his time on the ice and in the locker room that night, celebrating with his family and his team. “I just want to get back there.”

As CEO of the Bruins, Jacobs is in charge of the team’s business operations, but he also prioritizes its philanthropic endeavors. The Boston Bruins Foundation that he founded in 2003 and oversees today as chairman has raised more than $74 million to date. Meanwhile, he remains intensely focused on the on-ice product as well. He likes to watch the team’s morning skate and then tries to end meetings by 3 p.m. so he has time to exercise and eat before each game starts.

He does his best to avoid inflammatory conversations about the team that play out on the radio or in the papers. And he tries not to text decision makers right after a game, at least giving them the night before weighing in on what he saw. “He’s very passionate,” team President Cam Neely said. When Jacobs does send one of those texts, Neely said, “it just shows his passion.”

Away from the Bruins, Jacobs continues with his other competitive endeavor: riding horses. He grew up on a horse farm and has always been fiercely competitive during equestrian events, recalled his longtime friend Philip Richter. In 2017, Jacobs helped Team USA claim the top prize at the Nations Cup. “There’s no one else in show jumping doing what he’s doing, period,” Richter said, specifically noting Jacobs’s ability to adapt to each horse he rides, whether they’re temperamental or placid.

The Bruins championship in 2011 looked like it was just the beginning, but so far it has remained the pinnacle. The club managed to return to the finals two years later, and then again in 2019, but both campaigns ended in disappointment.

“I thought we had the best team in the league at the time,” Jacobs said of the painful 2019 loss, which culminated in a Game Seven defeat at home. He still remembers the barricades set up along the streets that night, the roads cleared of traffic in anticipation of a celebration. Instead, Jacobs walked silently down Canal Street. “Do you know that feeling you get when you lose something—maybe something you loved?” he said. “That takes a while to get over.”

The finals losses may still sting, but it’s impossible to deny that the Bruins have remained a successful franchise. Heading into last season, the team had made the playoffs for eight consecutive seasons, the longest such streak in the league. Ultimately, however, that season was nothing but a disappointment. The Bruins won their fewest games in a full season since 2005–2006 and didn’t qualify for the playoffs.

When it comes to expectations for the future, Jacobs said that the disappointment of last year changes nothing now that the 2025–2026 season is underway. The goal, as always, is to capture another Stanley Cup, especially now that his father is eighty-five years old. “I feel pressure that we’ve got to do this, we’ve got to win,” he told the Boston Globe earlier this year. “There’s nothing more that I would want to do as an executive, but also as a son, than to make sure that we get another championship while everyone’s still around to share it.”

Nearly a quarter century in, Jacobs keeps moving the franchise forward. He oversaw a $100 million renovation of TD Garden ahead of the 2019–2020 season that coincided with a more than $1 billion investment in the neighborhood that surrounds the arena, bringing a grocery store, movie theater, and corporate building to what had been a relatively barren patch of downtown Boston. The project was beyond anything his father had envisioned. For her part, Boston Mayor Michelle Wu called Charlie “a treasure in our community.”

From there, Jacobs turned his attention to the Bruins’ centennial season. The team arranged a yearlong series of celebratory events leading up to December 1, 2024, the one-hundred-year anniversary of the first game the Bruins ever played. As part of the festivities, the team unveiled a statue last fall to honor its first century, a ten-foot-long, 3,500-pound Bruins bear sculpted by Harry Weber.

The bronze statue debuted on a sunny Saturday afternoon in November, with Jacobs joined by local dignitaries and team icons. Unlike when he first joined the organization, there were no criticisms, no cries to sell the team, only well-wishers and autograph seekers. “This is a very special day,” Jacobs said to the gathered crowd. “While this statue pays homage to our past, it is also a beacon to our future. As we mark one hundred years of Bruins hockey, we should look forward to the next hundred with excitement and hope.” ◽

Jacob Feldman is a sports business reporter at Sportico and the founder of The Sunday Long Read, an email newsletter celebrating the web’s best stories.