Nightmare candidate to purchase Celtics could be all it takes to tear down a dynasty

Since Wyc Grousbeck announced he would be selling the Celtics back in early July Boston fans have feared one possible new owner. A recent report from the New York Post confirmed these fears as Fenway Sports Group is considering making a bid for the Celtics. Fenway Sports Group led by John Henry is the current ownership group of the Boston Red Sox.

The group has been highly controversial for their cheap tendencies and unwillingness to invest in successful rosters. Henry is already one of the most unpopular people in Boston and buying the Celtics wouldn't help.

In addition to the Red Sox Fenway Sports Group owns the NHL's Pittsburgh Penguins and the Premier League's Liverpool F.C. Adding an NBA franchise to this collection, especially the Celtics, makes a ton of sense for them. It's also worth noting LeBron James is a partner of Fenway Sports Group being part of an NBA ownership group would be very enticing for James post-retirement.

While Grousbeck put the team up for sale in July he plans to stay as the owner until 2028. Nevertheless, a potential sale to Fenway Sports Group would be a disaster for the Celtics. Let's dive into some of the negative consequences. 

The downside of John Henry and FSG

The biggest point of contention against John Henry as the Red Sox owner has been his unwillingness to spend money even on successful teams. Notably, the Red Sox traded Mookie Betts and let Xander Bogaerts walk in free agency. Both players were crucial parts of the Red Sox winning the World Series in 2018. Henry has also often ignored clear team needs such as defense and pitching. 

Grousbeck is one of the most hands-off owners in the NBA and has been more than willing to pay the expensive luxury tax bill for the Celtics. At the same time he has been very open to media appearances and speaking transparently when needed.

Going from this to someone who often avoids the media and criticizes fans when he does would be quite an unwelcome change. 

The Celtics cap situation

The John Henry and Fenway Sports Group reports are particularly concerning given the Celtics' current cap situation.

After winning the NBA championship Grousbeck and the front office did a wonderful job of retaining their core. This included handing out extensions to Jayson Tatum and Derrick White. Jaylen Brown and Kristaps Porzingis got extensions the previous offseason. Jrue Holiday was extended in the middle of the season.

The Celtics' championship core is locked up for the foreseeable future and this squad has all the makings of a team capable of winning multiple titles. However, the downside is that they are historically expensive.

The Celtics' entire starting five has an average annual value (AAV) of $30 million and the team's total payroll is over $200 million. Additionally, in the 2025-26 season, Boston will be paying more in luxury tax penalties than in traditional payroll making their total roster worth over $500 million dollars a year. This is challenging in the second-apron era. However, for a core capable of incredible success this is a price worth paying.

For Henry and FSG however, they would certainly take drastic measures to get under the second apron. Quite possibly even under the first-apron. Owning another team combined with his track record and the second-apron penalties would be the perfect storm.

Regardless of how good the team is in 2028, Henry would look to shake things up. Porzingis, White, and Holiday could be let go. Even if the value isn't right in a potential trade or worst-case Henry would let them walk in free agency. While it might sound crazy now Brown could be gone if Henry bought the team. Henry has proven he has no loyalty when it comes to keeping stars and Brown is the Celtics' second most expensive contract.

Ultimately, though 2028 is a long time from now and more speculation won't change anything about the situation. Nevertheless, it's clear Henry would be a poor fit for the Celtics. However, the Celtics are one of the most historic franchises and they have other options with this sale. Most notably, current Celtics co-owner Steve Pagliuca has known interest in buying the team. 

Where does LeBron fit in?

As mentioned before LeBron James is part of Fenway Sports Group. While he's playing now, by 2028 he very likely won't be. He currently owns about one percent of FSG's overall operations however, this will certainly increase once he retires. It would be ironic for LeBron to be a part owner of the Celtics after a career of being rivals with them. However, LeBron's likely involvement wouldn't be as problematic or influential as Henry's. 

LeBron has also discussed owning a potential Las Vegas expansion team with FSG. These plans would conflict and FSG will likely have to choice between one or the other. It's unclear what team the group will prioritize. However, LeBron's long-time connection to the Vegas expansion team could be a factor. Ultimately, this could save the Celtics from a dreaded ownership situation.