When the Portland Trail Blazers fell into the lottery last season, it was supposed to be a one-time thing. They had made the playoffs eight years in a row, but with Damian Lillard injured, they needed to take a gap year, reload, and come back strong in 2023. For a while, it looked as though they might happen. Portland held the No. 1 seed in the Western Conference almost one month into the season and remained in the playoff picture for most of the year.

Lately, however, things have grown dire. Portland has now lost 14 of their past 19 to fall to 31-40. They are four games out of a play-in spot with 11 to go, and after acting as a surprising seller at the deadline, their roster is thinner than ever. On Sunday, even Damian Lillard admitted that this season is probably over.

"We pretty much fallen out of the race for the 10th spot," Lillard said after yet another defeat. "I love to play, I love the competition and I haven't been ready to give that up. But it does come a point in time when do you stop putting your competitive nature out front."

The Western Conference is deeper than ever, and even bottom-dwellers like Houston and San Antonio figure to improve next season. Things aren't going to get any easier for Portland moving forward. Lillard has consistently made it clear that he wants to remain in Portland, but if things continue at this rate, it's worth wondering what purpose keeping would even serve. Lillard may want to remain in Portland, but without a no-trade clause, the Blazers are under no obligation to keep him if they believe a trade would help them moving forward.

At this stage, it's hard to argue against that idea. The Blazers have had more than a decade to put a winner around him and have consistently failed. If keeping him can't even yield a play-in spot during arguably the best individual season of his career, things are only going to get harder for the Blazers with time. Lillard is under contract for four more years after this one and is 32 years old. That deal could look ugly if it isn't moved soon.

All it takes is one stroke of luck to change all of that. It didn't look like David Robinson would ever win a ring in San Antonio, and then the lottery gods granted the Spurs Tim Duncan. If the ping pong balls send Victor Wembanyama to Portland, all of this could change. But relying on the lottery as a team that came into the season seemingly trying to win is an unwise strategy. If Portland really wanted to maximize its odds, it would have dealt Lillard before the season.

Instead, both sides have chosen limbo. Lillard can't go to a contender so long as he remains in Portland. The Blazers can't rebuild in earnest so long as they need to keep Lillard happy. Thus far, their compromises are satisfying no one. Portland just wasted another year of Lillard's prime. He doesn't have many more of them to spare.