At the 2025 NBA Draft Combine, presumed No. 1 overall pick -- and Maine native -- Cooper Flagg had a sit-down meeting with the Boston Celtics.
Draft prospects commonly have meetings with NBA teams in the predraft process; Flagg likely also met with other teams such as the Dallas Mavericks and San Antonio Spurs, who hold the top two picks in the draft. Boston, however, does not pick in the first round until 28th; there is no chance Flagg is dropping to the second pick, let alone the 28th.
Why would such a thing occur? Why would the Celtics even waste their time talking to an elite draft prospect when they seem to have no chance at drafting him?
Perhaps it's because a savvy front office is pursuing every potential avenue available to them in moving forward into the future. That future has suddenly been cast in fog after Jayson Tatum tore his Achilles in Game 4 of their second round playoff series against the New York Knicks, a series they officially lost in Game 6 on Friday night.
Tatum will likely miss the entire 2025-26 season, pulling the Celtics out of the ranks of true contenders for a season. At the same time, this roster is on track to be the most expensive roster in the history of basketball. Is the organization comfortable footing a gargantuan bill for a non-contending team? And what does that mean for upgrading the sustaining the roster given the team-building restrictions such an expensive team brings in the modern NBA?
What if the Boston Celtics had a path to reset the roster into a younger group to continue contending down the road around Jayson Tatum, and in the process landed a local star who could be the centerpiece of the Celtics for the next 15 years?
It's crazy, but it just might makes enough sense to work out. Let's look at this wild trade and see whether it makes sense for the Celtics to pursue.
Celtics build a trade for Cooper Flagg
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It is highly unlikely the Celtics can merely stay the course, take a year off, and then continue contending in 2026-27. Their supporting stars will continue to age and the roster will continue to get expensive. They can try to move off of a player or two for salary relief, but this is a team that is always trying to get better.
If they want to make a massive swing, Jaylen Brown is the name that has long been whispered in trade rumors. If they were willing to trade Brown -- which would obviously be a painful and difficult decision, as Brown is a top-tier two-way star who won Finals MVP less than a year ago -- their return could be enough to make something special happen.
The Philadelphia 76ers hold the No. 3 pick in the 2025 NBA Draft and are almost certainly looking for options to turn that into a player who can help them win in the present. A two-way wing like Brown would be an ideal fit alongside Tyrese Maxey, Quentin Grimes and Joel Embiid.
Yet landing the No. 3 pick doesn't do the Celtics a lot of good; they will have to spend a season just outside of the title picture, yes, but they are presumably not looking at a long-term rebuild. Landing any top prospect doesn't move the needle for them.
What the No. 3 pick would do is give them the ammunition to go after the No. 1 pick. Nico Harrison walks to the beat of his own drum, has a team that is even more win-now than the Celtics, and highly prizes defense. Enter Jrue Holiday, a Nike client who excels on defense and would be a fantastic fit next to Kyrie Irving in the backcourt.
How does it all come together? Here is the proposed trade:
The 76ers get an All-NBA level forward in Jaylen Brown, move off of Paul George's contract, and take a flier on Olivier Maxence-Prosper to balance the money. The Dallas Mavericks give up Cooper Flagg, but in doing so land an All-Defense guard in Jrue Holiday, the No. 3 pick and two future firsts, one each from the Celtics and 76ers.
The Boston Celtics take on the contract of Paul George, which is a real question mark moving forward. They also have to move on from Holiday (whose contract could be questionable moving forward itself) and Brown, which is obviously a colossal move.
In return, they get a plethora of veterans to match Holiday's salary, all good players who can help them contend or who can be broken up in trades to reduce salary. And they land local hero Cooper Flagg to pair with Jayson Tatum for years to come.
Is it worth it for the Celtics? The pairing of Tatum and Brown has propelled this team to years of sustained success, even if only one title. Flagg looks like a can't miss star, but he also hasn't done anything yet. Landing a potential All-Star on a bargain rookie contract could do wonders for sustaining a contender in 2026 and beyond.
This deal doesn't make them much cheaper; they likely would need to move off of one of those veterans from the Mavericks in a cost-cutting move. There is also the downside risk if George continues to break down as a player.
The upside of this deal, however, is enormous. Paul George could rebound if healthy and be a perfectly fine complementary wing -- overpaid, but able to contribute. Derrick White, Jayson Tatum and Cooper Flagg are a tremendous trio, with Flagg holding the potential to reach heights Brown never did.
This would be a risky trade, and it's so insane none of the three parties likely go for it in real life. But it makes enough sense to dream -- and dreams are the start of the real magic that happens in the NBA every day.