The Celtics may have won the Jrue Holiday trade — but the city of Boston lost

When the Celtics traded for Jrue Holiday in September of 2023, the basketball world unequivocally understood that Boston had acquired an NBA champion, an elite glue guy, and one of the league’s best defenders.

In his two-year Celtics tenure, Holiday checked nearly every box. Now, as part of the Celtics’ first offseason trade, he’ll head to the Portland Trail Blazers, who will send back Anfernee Simons and two second-round picks in exchange.

It’s hard to describe Holiday’s time in Boston as anything other than a massive success. After earning All-Defensive honors and shooting a career-high 42.9% from three in the Celtics’ title season, he served as a pivotal part of the dominant 2024 championship run.

When fans reflect on Holiday’s contributions, they’ll remember his clutch postseason moments, a 26-point Game 2 Finals explosion, and perhaps most vividly, his game-winning steal in Game 3 against the Indiana Pacers in the Eastern Conference Finals.

But, it’s everything off the floor — namely, his impact in the locker room and his award-winning philanthropic work — that will cement his legacy in Boston.

Throughout his years in Boston, those closest to the team emphasized that Holiday’s impact was rarely captured in the stat sheet. And, at every given opportunity, those around the Celtics praised Holiday for his selfless demeanor and presence in the locker room.

“He’ll do whatever it takes to win for his team,” Joe Mazzulla said on numerous occasions.

His mentorship regularly uplifted the youngest players on the roster. As a rookie, Jordan Walsh named him as the player he was learning the most from.

After a March game in Miami, Neemias Queta said Holiday’s leadership helped him through stretches in which his playing time varied.

“He’s big time for us young players that are trying to make our name in this league,” Queta said. “A guy like that, that’s so humble, helpful for everybody, so selfless…”

And, just a few weeks ago, in an appearance on the Garden Report, rookie Baylor Scheierman named the 35-year-old as the very last player he’d want to part ways with from the Celtics.

Away from basketball, the Holidays worked to uplift the Boston community

Jrue Holiday came to Boston to play basketball and contribute to an elusive championship. And, while Banner 18 will hang forever, one of the most profound impacts of his tenure has nothing to do with basketball.

Away from TD Garden, away from the Auerbach Center, and away from the cameras, Holiday and his wife, former Olympic soccer star Lauren Holiday, worked tirelessly to make the city of Boston a better place.

It’s nothing new.

The couple’s philanthropic journey began in 2020, after the murder of George Floyd at the hands of police. They decided to donate the entirety of Jrue’s NBA bubble salary — more than $5.3 million — and used that money to launch a social impact fund that elevated Black-owned businesses and nonprofits.

In its early days, the Jrue and Lauren Holiday Foundation (JLH Fund) centered around four cities: Los Angeles (Jrue’s hometown), Indianapolis (Lauren’s hometown), New Orleans (where Jrue played for seven years), and Milwaukee (where Jrue won his first NBA title). In its first four years, the fund awarded $25,000 to $50,000 grants to more than 150 Black-owned businesses and charities, while providing mentorship and resources that oftentimes far exceeded the financial support.

Back in 2023, Janitza Vasquez, who founded One Happy Mama, a New Orleans-based nonprofit dedicated to uplifting young mothers, told CelticsBlog that the JLH Fund was simply a “blessing.”

Alan Bacon, an Indianapolis-based artist who elevates the work of Black artists through his nonprofit, GANGANG, similarly asserted that Holiday’s arrival in Boston would elevate Black entrepreneurs across the city.

“We’re really excited for Boston to get Jrue because you’ll see a bump in impact investment in the community that’s truly authentic, that you don’t see every day,” Bacon said.

And, as those familiar with the couple nearly guaranteed, the Holidays almost immediately immersed themselves into the Boston community and got to work.

How the Jrue and Lauren Holiday Fund uplifted Boston

Last summer, Jrue and Lauren formally partnered with Jaylen Brown’s Boston XChange to provide $100,00 grants to ten Black-owned businesses and nonprofits, combining the proven JLH model with Brown’s expansive Boston network and public desire to create a Black Wall Street.

Grant recipients included: Future Master Chess Academy, a chess academy for the underserved communities that focuses on lifelong skills; Little Cocoa Bean Company, a cafe that creates culturally diverse and nutritious food for toddlers and kids; PYNRS, a streetwear-inspired performance running apparel company; Everybody Gotta Eat, a food culture and catering company, among others.

Brown and the Holidays regularly hosted “family” events for all of the cohort members. A few months ago, the entrepreneurs gathered for an emotional four-hour dinner at Brown’s home.

Grantees lit up as they described the experience of sitting at family-style tables, and chatting about both their lives and their joint vision for a more equitable future in Boston.

Amid a busy NBA schedule, it seemed the Celtics’ stars had all the time in the world.

“It was a very small, intimate group,” Tracy Skelly, the founder of Little Cocoa Bean Company, recalls. “We got to hear their thoughts on business in Boston, the equity gap in Boston, how they want to approach this work, how they think about capital, and really even social capital. How do they lend their names and their credibility to some of the work that we’re doing?”

The dinner wasn’t just business — it was also a chance to connect on a deeper, human level.

“We talked about things that mattered to us,” Skelly said. “We took pictures. We showed each other our babies. It was just a really nice occasion.”

Brown had never had a teammate willing to partner with him on his philanthropic endeavors to this degree, and expressed immense gratitude for the couple’s collaboration.

“Sometimes, you’re asking other guys, they’ve been advised not to be involved because of whatever reason, I don’t know,” Brown said earlier this season. “But Jrue and Lauren Holiday are great people. They’ve been doing this everywhere they go.”

Needless to say, the $100,000 given to each company in the cohort was hugely impactful.

For Lawyer Times, a longtime chess player and instructor who had doubled as a post office worker for more than 40 years, the financial investment allowed him to retire from government work and go all-in on the Future Masters Chess Academy.

Lawyer’s wife, Angela, credits Brown and the Holidays for their unwavering belief in the vision.

“The Holidays have such a giving spirit,” Angela Times said. “They just want to create community and bring people together.”

Similarly, Little Cocoa Bean Company was able to open a cafe location at the Boston Children’s Museum as a result of the partnership.

The Museum reached out to Skelly a year ago, inquiring about potentially bringing the family cafe to one of the city’s most popular family attractions. But Skelly said she didn’t have the resources to expand until she was selected to be a part of the inaugural cohort.

Less than one year later, the move to the Children’s Museum is happening, and Skelly has a lofty goal in mind: making meals entirely free for income-constrained families. The cafe is currently raising funds to provide 3500 free meals for families who visit the cafe. The JLH Fund and Boston XChange will match those 3500 meals.

Earlier this month, a few weeks after the Celtics’ postseason elimination, Little Cocoa Bean had a launch event at the Children’s Museum alongside Boston Mayor Michelle Wu.

Lauren Holiday showed up with a suitcase in hand before heading to the airport for a vacation with her family.

“She didn’t have to be there,” Skelly said. “Other celebrities that wouldn’t have been there, it would have been an inconvenience to them. There was no tangible return for her, but she was there, and she was supportive, and it really meant a lot to me.”

That’s been the experience of the Lawyer and Angela Times, too, who hosted a Juneteenth pop-up at the Museum of Fine Arts, thanks to a Holiday introduction.

“They show up,” Angela said. “They show up for events for us, and they’re our cheerleaders.”

Renee King, the founder of Fund Black Founders, which works with the JLH Fund, told CelticsBlog that Jrue and Lauren generally avoid media attention and publicity.

In fact, they can only be convinced to do interviews regarding their philanthropic work when those around them build a compelling case that the media coverage will help their grantee.

“They don’t do it for the fame,” King said. “They don’t do it for the publicity. They shy away — they would prefer not to be in the light at all.”

Still, Jrue Holiday won the NBA’s Social Justice Award last month.

Grantees entered the Celtics’ offseason worried about a Jrue Holiday trade

Last week, Lawyer Times tightened up when discussing the prospect of the Celtics trading away either Holiday or Brown.

“I talked to Lauren a little bit about it, about their future in Boston,” he said on Thursday, four days before Holiday’s trade to Portland was reported. “And, they’re concerned.”

If Portland opts to keep Jrue long-term, it’s almost guaranteed the city will become the latest beneficiary of the Holidays’ philanthropic spirit.

It’s the only way the couple knows.

“Being part of the community brings me joy — to see people in this city, people who love the city of Boston, love the team,” Holiday said earlier this season. “Every time we do an event, it’s an overwhelming feeling.”

In the meantime, the Holidays will be remembered by their off-court work by many.

“They have just been phenomenal in supporting our mission,” Skelly said.

Philanthropy is the lens through which (at least some) of Jrue’s Celtics teammates will remember him, too.

“Shoutout to Jrue and Lauren,” Jaylen Brown said earlier this season. “They’re forever good with me, just because of how willing they are to give to their community.”