Jaylen Brown Jrue Holiday Investment Returns for Round Two — And the Numbers Are Wild

It has been nearly a year since Jrue Holiday moved to Boston. After the trade, he moved the family to Portland, packed up the house, and began playing for the Trail Blazers, who this week managed to make it back into the postseason. When the moving truck left the driveway, his Boston chapter was closed by any standard accounting. And yet here he is, writing another $1 million check into the city he supposedly left with his wife Lauren and Jaylen Brown.

That has a subtle stubbornness to it. When they leave a city, the majority of athletes do so. They maintain the contacts, perhaps making an annual appearance at a charity gala, but the actual work usually goes wherever the next contract is. The holidays appear to run on a different schedule. The JLH Fund stays locked into any city it inducts, regardless of whether Jrue is suited up there, according to Renee King, who assists in running the fund. Until you see it in action, it sounds like a marketing ploy.

In the cozy aftermath of the 2024 championship run, the partnership with Brown began a year and a half ago. In an effort to provide funding to business owners from areas that Beacon Hill venture capital typically overlooks, Brown had been developing Boston XChange. Since 2020, The Holidays has awarded grants to over 150 Black-owned businesses in five cities, including New Orleans and Milwaukee. It was more of an acknowledgement that the two operations were already operating in parallel than a press conference.

A streetwear running brand, a catering business, a toddler food cafe, and a chess academy made up the first cohort. These are the small, oddly specialized companies that, due to the founders’ inability to quit their day jobs, hardly ever survive past the second year. The grant money was used by Lawyer Times, a forty-year postal worker and longtime chess instructor, to actually retire from the post office and work full-time at Future Master Chess Academy. In about a year, annual revenue increased from $50,000 to $300,000. When his wife Angela said something straightforward about the holidays, such as “they have a giving spirit, they want to create community,” it resonated in a way that only occurs when the speaker isn’t reading from a script.

The money may not be the most intriguing part of this story. On its own, a million dollars divided ten ways is significant but not revolutionary. Access—mentorship, introductions, and the village surrounding each founder—seems to be more important. The word “village” kept coming back to King. When you hear it, you think it sounds soft, but when you see the increases in revenue, you begin to question whether the soft stuff was really the leverage.

Applications for Year 2 will close on April 21. Another round of founders who are probably still in shock that two NBA champions are attending selection meetings, another ten companies, and another million dollars. Observing this from the outside gives the impression that Brown and the Holidays know something about Boston that the city itself occasionally overlooks: the most intriguing work is frequently already underfunded in the areas of the city that are least represented in the venture ecosystem.

It’s still unclear if this will develop into a long-lasting model that survives roster changes and playoff cycles. Once their careers end, many athletes stop being philanthropic. However, the Holidays have been doing this in five cities for the past six years without faltering. Additionally, Brown discusses a $5 billion wealth-creation goal for underprivileged Boston communities, which, depending on the day, may or may not be ambitious. In any case, he continues to appear. Jrue agrees. Lauren agrees. That was not altered by the trade and is unlikely to be altered by anything else.