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‘Who the hell is this guy?’ How Bill Chisholm closed the wildest deal of his life and bought…

Bill Chisholm had a humble upbringing on the North Shore, but made his way to the private equity world. “He probably felt like an underdog ... but he could outwork them all, and I think that’s been a driving force," his brother, Tim, said.

Bill Chisholm had a humble upbringing on the North Shore, but made his way to the private equity world. “He probably felt like an underdog ... but he could outwork them all, and I think that’s been a driving force," his brother, Tim, said.Erin Clark/Globe Staff

Earlier this year, Bill Chisholm spent several agonizing months finalizing his $6.1 billion bid to purchase the Boston Celtics.

If he was unable to raise the necessary funds by year’s end, the dream of owning his boyhood team would collapse and he would have to pay several hundred million dollars in penalties.

But in June, the private equity executive faced a more urgent issue while hiking through Virginia’s Blue Ridge Mountains: Are these rat snakes dangerous?

They moved slowly, and he was careful not to agitate them as he found an opening to maneuver by and continue north, never looking back.

For the last three years, Chisholm has spent weeks hiking sections of the Appalachian Trail alone, cooking on a portable stove and sleeping in a tent.

He has avoided bears in the Smoky Mountains, was once laid out by a tree limb while rushing to camp before sundown, and chased down a hiker who took his backpack. In the wilderness, he goes only by his trail name, “Skittles,” for the bag of the colorful candy he once brought to a group campfire.

Those close to Chisholm sometimes wonder why he puts himself through it. He is a 56-year-old billionaire with a wife and three children in their 20s who now owns one of the most prestigious sports franchises in the world.

Bill Chisholm on the Pearis Cemetery Trail in Virginia. Chisholm has been tackling the Appalachian Trail in two-week trips for the past three summers.

Bill Chisholm on the Pearis Cemetery Trail in Virginia. Chisholm has been tackling the Appalachian Trail in two-week trips for the past three summers.Courtesy Bill Chisholm

But his days of playing soccer for Dartmouth have long passed, and, like most men his age, he often wakes up sore now. So, in addition to the freedom and breathtaking views, he goes back every year because this unforgiving 2,200-mile tract that winds from Georgia to Maine provides an outlet for his competitive drive.

“I like to test myself,” Chisholm said, “and do things that are hard.”

That was part of his calculus when he called old soccer teammate and BDT & MSD Partners executive Gregg Lemkau in the summer of 2024 after his bank was hired to advise the controlling stakeholders, the Grousbeck family, on the sale of the Celtics.

Suddenly, it felt as if they were back in a Dartmouth dorm.

“Hey, Lem, I saw you were hired to sell the Celtics,” Chisholm recalled saying.

“Yeah, pretty cool, right?” Lemkau responded.

Chisholm agreed, and added that he wanted to buy the team that had coursed through his veins since he was a child. Lemkau thought Chisholm was making a joke.

“Dude,” he said, “you don’t have that kind of scratch.”

•••

Chisholm’s father, William Sr., grew up in Somerville, the second youngest of nine. He was an airline mechanic in the Air Force during the Korean War, put himself through night school at Suffolk, and worked for the Metropolitan District Commission for 48 years.

The elder Chisholm met Judith Brundage at his nephew’s christening in 1966 and wrote her phone number on a matchbook. The couple married in 1967 and settled in Georgetown. On Jan. 25, 1969, they had the first of three children: William Jr.

The Chisholm family: Bill is in the center with his father William Sr., mother Judith, brother Tim (left), and sister Robin (right).

The Chisholm family: Bill is in the center with his father William Sr., mother Judith, brother Tim (left), and sister Robin (right).Chisholm family

Sports provided the soundtrack at the family’s modest two-story, one-bathroom home on Marlboro Road, where a basketball hoop was attached to a tree with plywood, and a stone wall in a neighbor’s yard was called the Green Monster for Wiffle ball games.

Chisholm was 6 when the Red Sox lost Game 7 of the 1975 World Series. He sobbed so loudly his parents sent him to his room, where he began stomping the floor.

The Celtics, who won four NBA titles from 1976-86, provided warmth. Chisholm and his younger brother, Tim, had posters of Larry Bird and Robert Parish, and during the 1978-79 season, when Chisholm was 10, he and a cousin bought obstructed-view tickets from a Globe classified ad for $8 and went to the Garden for the first time. It was enchanting.

Chisholm delivered the Newburyport Daily News and the Lawrence Eagle-Tribune and showed his early business acumen when he persuaded his younger sister, Robin, to do half the route for 25 cents.

During high school, he dug ditches for an electrical contractor and bussed tables at a golf-course restaurant. That helped pay tuition at the Brooks School, a boarding academy in North Andover where Judith Chisholm worked as an administrative assistant so her children would receive a reduced rate.

The school mostly consisted of boarding students from wealthy families, but the Chisholms commuted in the family’s lone car, a Plymouth minivan that logged more than 220,000 miles.

Chisholm led the soccer team to the New England prep school title as a senior captain. Named a senior prefect, he had weekly meetings about the school’s policies and culture with the headmaster.

“He probably felt like an underdog, growing up in Georgetown and going to Brooks with people who had generations of wealth,” his brother, Tim Chisholm, said. “But he could outwork them all, and I think that’s been a driving force.”

•••

Chisholm was recruited to play soccer at Dartmouth and as a senior helped the Big Green reach the NCAA quarterfinals. He received a bachelor of arts degree and intended to become a teacher, but he was intrigued by the competitiveness of the finance world.

Bill Chisholm (second from left) played soccer at Dartmouth after a standout career at the Brooks School. His teammate, goalkeeper Gregg Lemkau (right), was later hired by the Grousbecks to facilitate the sale of the Celtics.

Bill Chisholm (second from left) played soccer at Dartmouth after a standout career at the Brooks School. His teammate, goalkeeper Gregg Lemkau (right), was later hired by the Grousbecks to facilitate the sale of the Celtics.Dartmouth Athletics Department

Near the end of their senior year, Kimberly Ford noticed Chisholm in a friend’s picture. A few dates before graduation led to a long-distance romance, with Chisholm, an analyst at PaineWebber in New York, sending handwritten poems to Ford in California, where she was a teacher.

They were walking through a park in Woodstock, Vt., in the summer of 1995 when Kimberly reached into Chisholm’s pocket to hold his hand and bumped into the engagement ring he was carrying.

“Well, I guess you know what I’m about to say,” he told her.

The couple settled in the San Francisco Bay area, where Kimberly earned her doctorate in foreign literature at Cal-Berkeley, and Chisholm worked at Bain & Company.

The three children: sons Will and Quentin and daughter Aidan inherited their father’s love of Boston sports.

After the Red Sox broke their curse and won the 2004 World Series, Chisholm popped a bottle of champagne and gave his children sparkling apple juice for a toast. At the time, he had dreams of becoming the Red Sox’ general manager. His mother-in-law even gave him a signed jersey from that team, and it still hangs in his Atherton, Calif., home.

Celtics games usually started around 4 p.m. Pacific time, so Chisholm would record them to watch with the family after work. Quentin, the youngest, could not wait.

“He’d be shooting hoops if they won,” Aidan said, “or hiding in his room if they lost.”

Eleven-year-old Aidan was inconsolable when the Celtics traded Kendrick Perkins and Nate Robinson to the Thunder in 2011, and the first time Kimberly heard Quentin swear was after the Celtics lost to LeBron James and the Heat in the playoffs that season.

Chisholm’s bedtime stories to his children were even Celtics-themed fiction. More recently, he would text the family videos of himself ― often in silly costumes ― hyping everyone up for the biggest games.

“I used to worry about him when his teams would lose,” Kimberly said. “But he’s actually pretty good about compartmentalizing, which is the only reason he’s still alive, I think.”

•••

In 1999, Chisholm started a small venture capital firm focused on early-stage companies. When the dotcom bubble wiped out so many dreamers, he pivoted to more established businesses.

Three years later, Chisholm co-founded the software-focused private equity firm Symphony Technology Group, and he became a shrewd dealmaker who found potential in flawed businesses. In one early transaction, he bought a struggling company that scraped data from UPC codes for about $100 million. Chisholm helped revive the business and sold it for nearly $1 billion about six years later.

STG now has more than $10 billion in assets under management, and Chisholm still starts each Monday meeting with a dad joke.

In the summer of 2023, Chisholm mentioned to his sister that he might invest in a sports franchise one day. The following July 1, just two weeks after the Celtics won their record 18th NBA championship, the Grousbeck family announced the team was on the market.

Robin, who lives in Cohasset, texted her brother.

“Celtics are for sale,” she wrote. “Just saying.”

Chisholm responded with just one word.

“Why?”

Similar questions swept through the basketball and finance worlds. After all, the NBA’s business was booming thanks to its imminent $76 billion media rights deal, and the Celtics were favored to repeat as champions, with franchise cornerstones Jayson Tatum and Jaylen Brown under contract for years.

“I was shocked,” Chisholm recalled. “I was like, ‘How can this be?’ ”

According to industry sources, there had been discussions within the Grousbeck family about selling in 2033. But the decision to divest sooner for estate and family-planning purposes was made in January by the family’s patriarch, 91-year-old Irv Grousbeck.

Irv’s son, Wyc, who has been lead owner since the family purchased the team from Paul Gaston for $320 million in 2002, thought it was too soon.

The arrangement was kept under wraps for months to avoid distracting a Celtics team hurtling toward an NBA title. When the news was made public, co-owner Steve Pagliuca, the second-largest shareholder, announced his intentions to be a bidder. Otherwise, rumors and curiosity swirled.

Chisholm hired Goldman Sachs as an adviser, and the firm’s research showed an eerily quiet market.

“It felt like if there’s a unicorn out there, if a Jeff Bezos is in the mix, forget it,” Chisholm said. “But I just didn’t hear that. It was like, ‘I like my chances here.’ The [Pagliuca] thing was a wild card, obviously.”

Within the organization, there was initially widespread hope that Pagliuca would become majority owner. And since he already owned about 20 percent, his pathway seemed clear.

•••

During the fall of 2024, prospective bidders met with Celtics management in Boston. Chisholm’s visit coincided with the team’s season opener against the Knicks, when the 18th banner was raised.

He and his family sat alone, but early in the third quarter Wyc Grousbeck brought them into the locker room, where they tried on his sparkling new championship ring and held center Luke Kornet’s size-16 sneakers.

Grousbeck and other executives were relieved that Chisholm’s passion for the team appeared authentic. He told a story about the 1980s broadcast crew of Bob Cousy and Gil Santos. He said how Leon Powe, a role player on the 2008 title team, was his favorite Celtic ever.

“This wasn’t what I wanted to do at all, sell the team,” Wyc Grousbeck said. “But if we’re going to sell it, I knew at the first meeting that selling to Bill would be a fantastic outcome.”

‘“This wasn’t what I wanted to do at all, sell the team. But if we’re going to sell it, I knew at the first meeting that selling to Bill would be a fantastic outcome.”’

Wyc Grousbeck, former Celtics owner

Chisholm submitted an initial bid in late January 2025, and later became a finalist, along with Pagliuca, Philadelphia Phillies minority owner Stan Middleman, and the Houston-based business consortium, the Friedkin Group.

He returned to Boston to meet with president of basketball operations Brad Stevens, and Grousbeck placed the 2024 championship trophy on a conference table to set the tone.

Stevens projected his computer screen onto a wall and shared a rare glimpse into his basketball mind. He described how big deals were finalized, and why others crumbled, such as a near-miss for then-Mavericks point guard Jalen Brunson. Chisholm was captivated.

“I try to be dispassionate and objective about these things, but this one was really hard, because it’s the Celtics,” Chisholm said. “I do plenty of deals and can win some and lose some and that’s OK, but this one I was so emotionally attached to.”

When the March 14 deadline arrived, Chisholm submitted his final bid at an initial valuation of $6.1 billion, which would increase to approximately $6.6 billion when the second part of the deal closes in 2028, thanks in large part to the media rights windfall.

Sources said the bid from Middleman was $100 million less than Chisholm, while Pagliuca trailed by about $500 million. But Pagliuca’s offer was fully funded, sources said, and despite Chisholm’s massive $1 billion pledge from the private equity firm Sixth Street, he had less guaranteed capital.

“The family felt an obligation to make sure they got the right price for their investors,” said Frank Ghali, chief executive of Jordan Park, an advisory firm that managed the sale on behalf of the Grousbecks. “But it extended beyond that, because it’s their legacy and they’re New Englanders, so they wanted it to be the right choice for the community.”

The final call would be made by Irv Grousbeck, who co-founded Continental Cablevision in 1963, and is now an adjunct professor at Stanford. He has stayed out of the Celtics spotlight for decades and was not a visible presence during the sale process. In fact, Chisholm has still never spoken with him. (Through a representative, Irv Grousbeck declined to comment for this story.)

Chisholm’s high bid and Boston connections made him an attractive candidate, but Irv Grousbeck had reservations about his lack of confirmed funding.

“Irv sort of said, ‘Listen, do you think he can go raise the money?’ ” said Lemkau, the BDT & MSD chief executive. “I said, ‘I can’t guarantee it, but I think there’s a 75 to 80 percent chance he can.’ ”

•••

Chisholm was in his Menlo Park, Calif., office March 15 when Ghali called and said his bid had been accepted and he would be the new lead governor of the Boston Celtics.

Chisholm muted his phone and screamed. He called his wife, and both started crying. He FaceTimed his children, and his smile spoke for him.

Bill Chisholm (center) and his family at a Celtics game in November. From left: Quentin, Aidan, Chisholm, wife Kimberly, and Will.

Bill Chisholm (center) and his family at a Celtics game in November. From left: Quentin, Aidan, Chisholm, wife Kimberly, and Will.Erin Clark/Globe Staff

Still, the deal was not final. Because of concerns about Chisholm raising the necessary capital, he had to commit to paying a massive break-up fee if he failed.

In the ensuing days there were tense negotiations over the amount of the fee, as well as Chisholm’s deadline to raise the money to purchase the team. Chisholm said the sides were far enough apart that he feared the entire deal might collapse.

Quentin Chisholm happened to be visiting his parents that week, and he and Kimberly watched nervously at home as Chisholm paced the hallways and wore out his iPhone trying to close the biggest transaction of his career.

“I’d just be sitting there reading my book in the living room,” Quentin said, “and he’s making these crazy, intense business calls.”

On March 19, four days after he was chosen as the winning bidder, Chisholm was scheduled to fly across the country to pursue a big investor but ended up stranded at San Jose’s airport for six hours with Ghali, Irv Grousbeck’s lead representative, because discussions had reached a stalemate.

Chisholm said being unable to negotiate directly with the elder Grousbeck was challenging. In any other scenario, he said, he would not have agreed to that setup. But this was the Celtics. Now, Grousbeck seemed to be losing patience as he sought closure.

“Irv was very effective,” Chisholm said. “He was basically placing deadlines, like, ‘Frank, if you don’t get this signed in the next five minutes, you need to go home.’ It was very tactically effective and probably took years off my life.”

Wyc Grousbeck (left), his father Irv, and Steve Pagliuca in 2003. Ten days after the Celtics won the NBA title in 2024, the Grousbeck family announced the team would be sold.

Wyc Grousbeck (left), his father Irv, and Steve Pagliuca in 2003. Ten days after the Celtics won the NBA title in 2024, the Grousbeck family announced the team would be sold.Davis, Jim Globe Staff

Later that day, the sides agreed Chisholm would have until Dec. 31 to fully fund the transaction, and that he would pay a substantial break-up fee if he couldn’t. Chisholm declined to reveal the exact figure, saying only it was “several hundred million dollars,” and that the Grousbecks had sought more.

“That was my biggest calculated risk of the whole deal,” Chisholm said. “I wouldn’t say it was irresponsible, but it was a risk.”

With the agreement finalized, Chisholm had congratulatory FaceTime calls with Stevens, Celtics coach Joe Mazzulla and forward Al Horford, and significant investors coalesced around him.

Celtics minority owner and telecommunications executive Rob Hale, who had stayed independent while alliances formed among finalists, made a pledge that would make him the third-largest individual shareholder. Real estate mogul Bruce Beal Jr., a Lincoln native, also became a key member of Chisholm’s group.

Aditya Mittal, chief executive of a global steel giant, had explored a bid to become lead governor but eventually backed Chisholm with a $100 million commitment. Mittal’s interest swelled during visits to Boston, though, and he upped his stake to $1 billion and became alternate governor.

Pagliuca also released investors from his group, allowing them to join Chisholm. And Wyc Grousbeck, who remains a visible presence within the franchise, wound up with a 13 percent stake. It will be reduced to about 3 percent when the second phase of the deal closes in 2028.

Chisholm’s fully funded bid was approved by the NBA in August, five months before his deadline.

“Bill was always the one people were like, ‘Who the hell is this guy? Does he even have enough money,’ ” said Lemkau, who bought Chisholm a Leon Powe jersey on eBay when the deal was completed. “He laid in the weeds quietly, and people underestimated him, and he kind of pounced.”

•••

Chisholm smiles as he steps into his office at the Auerbach Center and sees a pile of crisp Celtics gear on his desk. These small perks of his new position still delight the fan in him.

Above his computer hang pictures of Celtics greats Dave Cowens and Reggie Lewis, and one of Kevin Garnett, Paul Pierce, and Ray Allen with the 2008 championship trophy. Chisholm is energized by the thought of chasing another.

But, as the Celtics attempted to repeat as champions last season, a grim reality loomed. A roster revamp would be needed to avoid severe penalties for being above the salary cap’s second apron. And when Tatum ruptured his Achilles tendon last May, it further altered the road map. Stevens called Chisholm in July and essentially apologized.

“We have to retool,” Stevens recalled telling him. “Like, we just have to.”

The Celtics, who were projected to have an NBA-record salary and luxury-tax bill of about $540 million this season, shed about $300 million with the departures of veterans such as Horford, Kristaps Porzingis, and Jrue Holiday.

The moves were necessary, but the optics of the financial reset coinciding with Chisholm’s arrival made him easy fodder for casual fans. Chisholm was unbothered. He did not acquire the Celtics for the profits and insists that investments don’t increase in value by penny-pinching, anyway.

“I made money in my life so I could do this,” he said. “And we’re going to do whatever we can to win.”

Bill Chisholm and his wife have been spending more time in Boston — and he has been spotted courtside at plenty of Celtics games.

Bill Chisholm and his wife have been spending more time in Boston — and he has been spotted courtside at plenty of Celtics games.Barry Chin/Globe Staff

After an 0-3 start, the Celtics have improbably resurfaced near the top of the Eastern Conference. What was once viewed as a gap year now seems rife with possibility, with Tatum’s potential return a tantalizing subplot.

“Bill does not like to lose and he doesn’t have much experience with it,” said his sister, Robin, “so being Boston fans, that bears well for us.”

•••

“Finally going to sleep in a shelter tonight! I figured I had to experience it at least once, and this shelter comes highly recommended, both based on location (out of the wind) and a general lack of mice. (By the way, I just got a whiff of myself and I smell terrible.) There are two others here right now. I point-blank asked them if they are snorers and they claim not so much, but we shall see.” — May 2, 2024, excerpt from Bill Chisholm’s travel journal

The Appalachian Trail stretches from Springer Mountain, Ga., to Mount Katahdin in Maine. It first piqued Chisholm’s interest when he was at Dartmouth and saw hikers pushing through Hanover, N.H., often stopping at Lou’s Restaurant and Bakery on Main Street for a free slice of pie.

Bill Chisholm on Roan Mountain in Tennessee.

Bill Chisholm on Roan Mountain in Tennessee.courtesy Bill Chisholm

Later in life, he knew his commitments to his business and family would not allow him to disappear for months, so he has split his journey into annual two-week segments. He trained by walking on a treadmill wearing his 30-pound pack and practiced pitching his tent outside his California home.

He started in May 2023, and completed about 300 miles in each of his first two trips. Last spring’s trip was delayed because of Celtics playoff games, so he managed closer to 150 and stopped in Virginia, near the Shenandoah Mountains.

“The beauty is no one knows my name and no one asks what you do,” Chisholm said. “It’s all about what you’re going to have for dinner because you’re so hungry. How many miles did you do? What snake did you almost step on?”

The closest friend he made on the trail, Michael Elliott of Jacksonville, Fla. — trail name T-Bone — was stunned when he learned during an interview for this story that Chisholm owns the Celtics. It had never come up.

Chisholm knows it will become increasingly difficult to maintain his anonymity. He and Kimberly recently bought an apartment in a downtown Boston high-rise and prefer to spend their time cooking at home and watching reruns of “The Office.”

But it has been a joy to be back in Massachusetts, where he has more cousins than he can name. Judith Chisholm, who proudly shared news of her son’s big purchase with everyone at her Duxbury senior living community, already has attended three games with him. (William Sr. died in 2017.)

Chisholm has been an anxious and enthusiastic presence at TD Garden, just as he was as a 10-year-old who bought obstructed-view tickets with his paper-route money. Now, he sits a few steps from the Celtics’ bench. But he is not there to be seen, or to monitor his investment. He is there because it is exactly where he has always wanted to be.

Adam Himmelsbach can be reached at adam.himmelsbach@globe.com. Follow him @adamhimmelsbach.

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