For at least the next four years, the Milwaukee Bucks and Portland Trail Blazers have no choice but to be tied to each other. The blockbuster deal that sent Damian Lillard to America's Dairyland tied up Milwaukee's future draft picks with the Blazers through 2030 in a transaction that derailed the Bucks' ability to reshape their roster for years to come.
There was no predicting that Damian Lillard would tear his Achilles tendon in a first-round Playoff matchup with the Indiana Pacers. It was a noble effort to bring a Top 75 all-time player to town as the Robin to your franchise star's Batman. With that said, the Lillard pairing with Giannis Antetokounmpo never hit the ceiling that fans and front offices alike envisioned when GM Jon Horst executed that trade in the fall of 2023.
Now, the two organizations are in very different places. Milwaukee is pondering its future as the yearlong trade saga with Giannis seems to be coming to a head at the same time that things are falling apart in Portland.
Businessman Tom Dundon bought the team in March and was making waves by April. Just as the team emerged with an exciting young core scrapping its way through the early rounds of the postseason, Dundon immediately proved himself to be one of the biggest penny-pinchers in a league that's not designed for that type of approach.
Dundon has cheaped out at every turn early in his Blazers tenure. It started with not flying two-way players out for Playoff games, putting harsher restrictions on their use of hotel rooms, and failing to offer Playoff t-shirts to the dedicated hometown crowd. Things got much worse in Portland when Dundon laid off 70 Trail Blazers staff members in vital roles throughout the organization. He's also rumored to be limiting the team's head coaching search to save a few dollars on salary.
This may not seem like a problem the Milwaukee Bucks will have to deal with, but as the reality of a potential Giannis trade looms closer, it could have more of an impact than meets the eye.
What does the Trail Blazers' ownership drama have to do with the Milwaukee Bucks?
Portland possesses swap rights on the Bucks' 2028 and 2030 first-round draft picks — two of the assets they'd covet most in any Giannis trade right now. Without the ownership of their draft selections, Milwaukee cannot properly rebuild through traditional channels and has a wide range of restrictions on which draft picks it can trade.
This makes them a natural suitor in a Giannis trade, but if he's unwilling to pay the players already on his team or staff within the building, why would Dundon want to move off of young, cost-controlled talent in the form of first-round picks? It makes the likelihood of the Blazers getting involved in a Giannis trade, as a third party or as the team receiving the superstar player, much lower.
By that same logic, it probably eliminates them from considering a Giannis trade in the first place, as the 31-year-old is due a massive long-term contract extension later this offseason, and it's assumed that any team that would trade for him is willing to offer it.
In the grand scheme of things, this likely won't be the deciding factor one way or another in what happens between Giannis and the Bucks. But it is a sneakily underrated factor in the equation, which could push Milwaukee into accepting a suboptimal deal for the franchise star.
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