Exploring the Celtics' Dilemma: Deep Pockets or Deep Roots?

Deep pockets or deep roots? Analyzing the Celtics' sale dilemma As rumors swirl about the potential sale of the Boston Celtics, fans are left wondering what the future holds for their beloved team. With talk of wealthy investors and corporate giants vying for ownership, the question arises - should the Celtics prioritize deep pockets or deep roots? On one hand, having a billionaire owner with seemingly limitless resources could pave the way for big-name signings and extravagant upgrades to the team's facilities. However, a new owner with no emotional ties to the city or its basketball tradition could risk alienating long-time fans and losing the team's identity in pursuit of profit. Conversely, selling to a local investor or group with strong ties to the community could ensure that the team remains rooted in its Boston heritage. This could foster a sense of loyalty and pride among fans, who value the team not just for its on-court success, but for its role in the city's culture and history. Ultimately, the Celtics' sale dilemma comes down to a choice between financial success and staying true to their roots. Will the team prioritize deep pockets and potential championship glory, or opt for deep roots and the loyalty of their devoted fanbase? Only time will tell.

Deep pockets or deep roots.

That feels like the dilemma that Celtics fans -- and maybe even the Grousbeck family -- is about to navigate as the team installs a new majority owner.

Do you prefer someone with a connection to the city at the helm, or just want someone with a limitless checkbook who can keep this championship roster intact long term? In most spots, this is an easy decision: Find the person with the biggest bank account and let the fun begin.

As the Celtics like to point out, it’s different here.

All has been quiet -- maybe a little too quiet -- on the ownership front this summer after Boston Basketball Partners LLC announced their intent to sell a majority stake of the Celtics in the immediate aftermath of Boston’s title season. Their press release suggested a sale by the end of 2024 or early 2025.

Back in July, during an appearance on CNBC, Wyc Grousbeck noted, “We haven’t even begun the [sale] process but the [Grousbeck] family has agreed to find a new ownership group coming in that will make everybody proud of the Celtics moving forward.”

Everyone’s definition of “proud” is probably slightly different. Some will proudly embrace an outsider if they are willing to write the checks for the unprecedented luxury tax bills the Celtics are steamrolling toward. Others will be proud if the Celtics install a group helmed by someone with a connection to the team, particularly someone with ties to the most current ownership group.

Current Celtics co-owner Steve Pagliuca has already expressed a desire to bid for the Grousbeck family shares. The question is whether he can create a group with enough money to outbid any of the tech billionaires that might emerge as a suitor.

On his podcast this week, Bill Simmons noted how whispers have increased about Amazon owner Jeff Bezos potentially joining the bidding for the Celtics.

The speculation has always been that Bezos would be most interested in a potential Seattle expansion team, especially with Amazon headquartered there. It’s also not hard to reason why a billionaire would be interested in buying a franchise like the Celtics, with the 18 championship banners and ready-to-add-more roster eliminating the painful growth process of any new team.

It feels inevitable that more names will join the fray in the coming months. Depending on if you’re Team Roots or Team Pockets, your first question will either vet their local connection or their valuation. Your second question probably answers whatever query you didn’t ask first.

It’s all a little reminder of how spoiled we were here for the past two decades. Grousbeck and Pagliuca bought the Celtics at a time when Banner 17 felt far away. They installed Danny Ainge as general manager, swung back when the ping pong balls defied them, and quickly delivered a title. They didn’t have the deepest pockets, but they cared about the history of the team and prioritized it.

That ownership group had limits on their spending, but were willing to pay to contend. They paid the luxury tax any time the team felt like it had an honest chance to chase a title. But those tax bills simply become untenable moving forward.

Will the next owner be willing to stay in the shadows the way this ownership group often has? Will they let Brad Stevens and Joe Mazzulla do their jobs without meddling?

The Grousbeck family’s last order of business potentially could be delivering the team to an owner who will feel a responsibility to uphold the tenants of this past group; an owner who will embrace the priorities of this team, regardless of whether they fully understand those responsibilities when they take the reins. But it’s also understandable if they simply have to defer to the highest bidder. At the end of the day, this is business.

It’s a little different for fans. So, deep roots or deep pockets?

In the short term, it sure feels like the latter is better to ensure championship success. But having a little bit of the former could go a long way in the long run.