I am a product of the 1990s. I still have a fondness for Pearl Jam, South Park, and I reminisce about the glory days of Marcus Camby and UMass basketball. As time passes, our memories tend to fade, or our imagination magnifies past experiences, making them seem larger, greater, and sometimes much scarier than they actually were in real-time.

Today, I believe that the Pearl Jam concert I attended on July 11, 2003, at Great Woods in Mansfield, MA, is the greatest rock ‘n’ roll achievement in history. Whether I felt that way in the moment is immaterial, as I now “know” that it was truly the most outstanding rock concert ever.

On the other hand, my recollection of the 1990s Boston Celtics and their ownership is exceptionally dreadful. The team ranged from truly bad to nearly mediocre. (Of course, that memory isn’t entirely accurate, as the early ’90s Celtics teams led by the late Reggie Lewis and an aging Big Three were actually quite good.) At that time, the Celtics were owned by the largely forgettable Paul Gaston. He was the most disinterested owner a team could have. The general sentiment in the city was that he couldn’t care less about basketball, and he cared just a bit more than that about the Celtics. The team had been handed down to Paul Gaston by his father, and his ownership is remembered for three main things: kicking Larry Bird to the curb, hiring Rick Pitino, and avoiding investment in the team on the court (especially when it came to the luxury tax). When Gaston sold the team in 2003 to an investment group led by Irv Grousbeck, I was thrilled—not because I was enamored with the new ownership group (I had no idea who they were), but because that guy, Gaston, was finally gone.

Paul Gaston is primarily why I am apprehensive about the Celtics’ new ownership group led by Bill Chilsolm. My apprehension is mostly unfounded, as there are giant distinctions between Gaston and the new owners. Gaston inherited the team from his father, whereas Chisholm and his group of investors just purchased the franchise for a record $6 billion. Gaston was often indifferent toward the hometown team, but Chisholm and his family genuinely care about the Celtics and want to see the franchise thrive both on and off the court. When Gaston sold the Celtics, the franchise seemed far from successful. In contrast, the current Celtics are recent champions, boast exceptional management, have two of the best wings in the game, and have been one of the NBA’s premier franchises for the last 20 years.

Despite this, my concerns about this new ownership group and the overall future of the franchise may not be entirely unfounded.

As expected, the 2025-2026 season is shaping up to be a transition year for the franchise. Jayson Tatum is recovering from an Achilles tear and will likely miss the entire season. Management had to cut salaries to avoid second apron penalties and will likely make further moves to get under the first tax apron as well. Getting under both aprons makes sense from both a team-building and financial flexibility perspective. The penalties for being over both the first and second aprons are significant, so it made strategic sense to make these changes during a “transition” season.

The decision to get below the second apron, and likely below the first before the conclusion of the 2025-2026 season, has been viewed as a straightforward choice from a team-building perspective. I agree that it was the right call, but it’s also presumptive to label it as a no-brainer.

First, let’s address the obvious. The trades that the Celtics made this offseason were mainly financially motivated, and they clearly weakened the team on the court. The trade of Kristaps Porzingis and Jrue Holiday resulted in acquiring Anfernee Simons, an undrafted rookie free agent, and one less second-round pick. Given the circumstances, Brad Stevens and his team did well to avoid giving up more assets to shed the salaries of Porzingis and Holiday. It’s also fair to argue that dealing Porzingis (a declining asset) and Holiday’s expensive contract right now made sense from a basketball standpoint.

However, it’s difficult to argue that the Celtics are in a better position for the 2025-2026 season compared to if they had kept Porzingis and Holiday, absorbing the team-building penalties. Had Porzingis and Holiday remained on the roster, one could reasonably argue that the Celtics might still be a top 4 team in a weakened Eastern Conference, possibly just a Jayson Tatum return from injury away from being competitive in late May and early June. This perspective has its flaws, of course, but the scenario isn’t impossible.

This brings me to some questions regarding the ownership group. Were the offseason moves driven by basketball strategy and team-building, or were they primarily financial decisions? If Jayson Tatum hadn’t suffered a serious injury, would the offseason approach have been different? Most importantly, what should we expect from this ownership group going forward? Several Celtics beat reporters have suggested that the team might aim to stay below both tax aprons and the luxury tax line to try to avoid paying the repeater tax over the next two seasons. It’s important to note that there are no team-building penalties associated with bypassing repeater tax penalties—only financial ramifications.

Bill Chisholm and his group just purchased the Celtics for $6 billion. That’s a billion with a “B.” Forgive me for not caring if they can save tens of millions in repeater tax penalties. My primary concern as a fan is that they do everything in their power to assemble the best possible team year in and year out. I’m not interested in the financial interests of billionaires concerning the Celtics.

Realistically, most of my fears may be unfounded. This ownership group and management team will likely strive to build a perennial contender, even if they are somewhat cautious about spending. But I’m a child of the ’90s; “Seinfeld” was “real and spectacular,” “Saving Private Ryan” is the best movie ever, and Michael Jordan is the GOAT. The thought of Paul Gaston still makes me a little queasy. Here’s hoping for the best…