The Portland Trail Blazers made it to the NBA Playoffs for the first time since the 2020-21 season. They are tied 1-1 with the San Antonio Spurs. And the team is doing it all without Damian Lillard, banking heavily on Deni Avdija. Interestingly, last year the veteran guard returned home after the Milwaukee Bucks waived him. With Lillard back on a bargain $14 million deal, the Blazers improve almost instantly, but that also raises the stakes.

Now, the front office feels the need to go all in and chase another star—maybe Giannis Antetokounmpo? According to Bill Oram of The Oregonian: “The Blazers are prepared to make a pitch for Giannis Antetokounmpo as long as he is willing to sign an extension, but are not likely to limit their options to Lillard’s former Milwaukee teammate.”

Does it feel like the Trail Blazers under Tom Dundon’s leadership are chasing a Giannis-Damian reunion? Yes. But they are also looking at other star options. Going back to July 2025, the Bucks had entered their second month of postseason play with an early playoff exit against the Indiana Pacers. Lillard’s ACL injury was still fresh, and many had believed that the Milwaukee Bucks might keep him for another season, give him the chance he missed due to the injury.

However, they waived him and stretched the remaining $113 million on his contract over the next five seasons. Meanwhile, they signed the Pacers’ big man, Myles Turner. Well, it’s safe to say that since Lillard’s exit, Giannis Antetokounmpo has experienced nothing but a massive downfall. Their 2025-26 season ended without a playoff entry. They finished 11th in the East with a 32-50 record. That’s not all. The rumors around the Greek Freak’s possible summer exit have kept the fire blazing in the trade market.

At present, as much as Giannis says he wants to stay in Milwaukee, the front office is seemingly keeping him aside from any active decision-making. Now, following their disastrous season, Doc Rivers left the position of head coach. On Wednesday, the team announced ex-Grizzlies HC Taylor Jenkins as the new leader. And according to ESPN’s Shams Charania, the front office didn’t involve Antetokounmpo in this search process.

“I’m not aware of any involvement from Giannis in this search process. This was something that the Bucks genuinely led…my understanding is that there’s been zero communication between these two sides since the deadline as far as Giannis and the organization’s top brass,” he reported.

Well, it’s hard to say how deep the cracks have gone between the Bucks organization and the 2-time MVP. But if he chooses to walk away from the team this summer, then the Portland Trail Blazers are going to have their doors open. Tom Dundon won’t mind spending a fortune on a game-changer.

Can the Trail Blazers afford Giannis Antetokounmpo?

New owner Tom Dundon has no plans to cut costs when it comes to the roster. He has already told the front office he is fully willing to dip into the luxury tax if it means landing the right player. Meanwhile, the Portland Trail Blazers are already walking a financial tightrope. Their total cap sits at $231,140,276, which is $-66,140,276 over the limit, while their projected cash payroll stands at $170,197,298. Meanwhile, Giannis Antetokounmpo is set to earn a massive $58,456,566 in 2026-27. That gap feels daunting. However, the roster reveals flexibility if the front office gets bold.

Start with the heavy contracts. Jrue Holiday earns $34,800,000, and Jerami Grant takes $34,206,898. Moving both nearly matches Giannis alone. Add Shaedon Sharpe at $20,089,287 or Toumani Camara at $18,080,358, and the math starts working cleanly. Even Scoot Henderson at $13,585,523 or Anfernee Simons’s replacement-level deals like Deni Avdija at $13,125,000 create breathing room. The puzzle pieces are there.

Then comes the gamble. Damian Lillard at $13,398,000 remains a bargain centerpiece. Young pieces like Donovan Clingan at $7,519,920, Kris Murray at $5,315,004, Yang Hansen at $4,643,520, Vit Krejci at $2,667,944, and Sidy Cissoko at $2,497,812 add depth but also trade chips. So yes, Portland can afford Giannis. The real question is how much of its soul it is willing to trade away. And if they truly have a Giannis-Dame reunion, then the 36-year-old veteran is untouchable.

Therefore, Portland stands at a clear crossroads. The push is real, and so is the risk. They want Giannis, yet they refuse to stay limited. Meanwhile, Milwaukee’s uncertainty keeps the door open. Dundon is ready to spend, and the roster can shift. However, every move carries weight. And this chase might define the Trail Blazers’ identity and future.