Tom Dundon is an enigma. In Portland, we don’t know the guy. I expect that will change once his expected purchase of the Trail Blazers goes through, but for now, how he will run the franchise is a bit of a mystery.
As such, we have no choice but to take the few things we know about him at face value.
For one, he seems to really like wearing ballcaps. He’s one of us!
But he is also known as a hard-driving boardroom shark who will not tolerate losing, who is not afraid to be bold and is not particularly patient.
Let’s put aside for the moment what that means for the Blazers’ future at Moda Center and in Portland — which should come into sharper relief in Salem with the upcoming legislative session — and instead focus on what it means on the court.
When Dundon emerged as the Allen Estate’s preferred bidder back in September, an anonymous source close to Dundon explained the billionaire’s competitive nature to The Athletic by saying, “If Tom was the owner last year, he would have been trying to get Luka. He would be like, ‘Why should the Lakers get him?’”
What that portrayal might lack in substance — any executive or owner who wouldn’t have tried to get Luka Doncic, were he ever widely available, should be stripped of decision-making power — it makes up for in spirit.
The new guy is gonna want to go for it.
Which brings us to the conflict du jour in a league that never seems to be lacking for drama.
Giannis Antetokounmpo wants out of Milwaukee. If it’s a superstar Dundon wants, here’s his chance.
Now, plenty has changed since last spring when I wrote that the Blazers had the tools to pull off a deal for the two-time MVP if they were so inclined. Dundon has entered the fray, Damian Lillard has returned and Deni Avdija has emerged as a legitimate franchise-building block and likely All-Star.
Here’s what hasn’t changed: After swindling Milwaukee in the Lillard trade, the Blazers essentially hold the Bucks’ first round draft picks in three consecutive drafts starting in 2028. In the first and third years, those exist in the form of pick swaps, meaning if the Bucks are slotted to draft higher than the Blazers, Portland has the right to switch spots.
Without Antetokounmpo, the smart money says the Bucks will stink in those years. So as much value as those picks are coveted around the NBA, they have even more value to Milwaukee, which would be able to control its own destiny if it got them back.
The Blazers hold the cards.
Do they want to get in the sweepstakes for Giannis? Use those picks to help facilitate a three-team deal? Or hang on to those future selections for themselves and trust that the Bucks will deliver them high lottery picks?
Dundon’s looming presence makes this an even more intriguing question. To be clear, he won’t own the Blazers by next Thursday’s trade deadline. It would be a violation of NBA bylaws for him to instruct general manager Joe Cronin to act one way or another.
But Blazers executives have all gotten to know Dundon over the past five months. They no longer need to guess what he values and what kind of vision he has for his franchise.
As such, the question of whether the Blazers get involved in this whole affair or not is actually less interesting to me than the psychology of the franchise moving forward. Trading for Antetokounmpo, regardless of the outbound package, would immediately elevate Portland to contender status. When you have a player of that caliber, that is the standard by which you live.
What is the ceiling for the fully realized version of the Blazers current core in the next couple of years, cautiously accounting for a healthy Lillard? Is it a team that you feel confident can win more than, say, one playoff series?
Put differently, are the Blazers better off short-circuiting their path to contention by bringing in one of the league’s top few players, a 31-year-old superstar? Or should they continue to organically grow and maintain the flexibility they have with no assurances of ever finding that superstar?
We all know the deal in Portland. You can’t sign a star in free agency. If you don’t draft well — and for the most part, the Blazers haven’t — then your only path is through trades. That’s an area where Cronin has excelled. See: Avdija.
But if it were me, I’d proceed with caution when it comes to this particular episode of NBA star search. The Bucks will almost certainly insist on getting Avdija back. Cronin should resist that not merely because of the player Avdija is but because of the value he represents.
On a declining contract, Avdija may be the best per dollar investment in the NBA. Contending teams would happily surrender several draft picks to get him. If the Blazers gave Milwaukee back their picks, plus Avdija, it would represent the opportunity cost of more than half a dozen draft picks.
That is dangerous territory just to recreate the Giannis-Dame pairing that has already failed once elsewhere, with both players well into their 30s, Lillard recovering from a catastrophic injury and Antetokounmpo holding the option to become a free agent in 2027.
While the team that trades for him will have a huge advantage in being able to pay dramatically more, the flight risk, especially in another small market like Portland, would be real.
How, I wonder, does a bet-on-himself guy like Dundon see it? It will become a real question if Antetokounmpo remains in Milwaukee past the deadline and his certain exit is pushed off until the summer.
Will the new owner want to tread lightly? Or does he want to be the owner who moves heaven and earth to bring in a superstar that would make his new team a championship contender?
Will he be calculating and deliberate? Or will he channel Les Snead?
Snead, the Los Angeles Rams general manager, memorably wore a t-shirt that read, “(Expletive) them picks” after his aggressive trades led the Rams to a Super Bowl win three years ago.
And it’s true. If the result is a championship parade, who cares what you do in a draft years down the road? In that case, “(Expletive) them picks,” indeed.
It would be out of character for the Trail Blazers as we know them to swing for the fences in such an aggressive way. It would probably be most wise to get involved in a Giannis trade as the third team, if at all, and bring another core player who is on the same timeline as Avdija, Toumani Camara and Donovan Clingan.
But Dundon’s forthcoming arrival has the potential to upend that thinking and his new team’s entire basketball strategy.
There is little doubt that the new owner will demand that the Blazers be bold, the only question is when?