For Damian Lillard and the Portland Trail Blazers, the time to make a big move is now

For the second straight year, the Portland Trail Blazers are on the outside looking in terms of the NBA playoffs with a 33-44 record. Star guard Damian Lillard is coming off one of the best seasons of his career, with a career-high in points (32.2 a game) and averaging 7.3 assists. In a current age where a collection of stars are needed to make a championship push, it’s been at least admirable that Lillard has been adamant that he wants to bring a title to Portland. But even if you use the Giannis Antetokounmpo parallel in Milwaukee, the Bucks added players like Jrue Holiday and Brook Lopez in addition to the emergence of Khris Middleton, which ultimately led to a title in 2021.

Entering the 2023 offseason, the Blazers and Lillard appear to be at a crossroads in their course of action. Portland has an excellent young player in guard Anfernee Simons and another good scorer in All-Star forward Jerami Grant – coming off a season where he scored 20.5 points per game and 40.1 percent from 3-point range. However, Grant is a free agent and will ask for considerable money. Will the Blazers pay that and then try to get some frontcourt help?

Then there’s the question of a potential lottery pick the Blazers can get (they only have a 10% chance to get the first pick overall). It’s most likely the team will trade the pick if they don’t win the Victor Wembanyama sweepstakes, especially considering Lilliard’s recent comments about wanting to “go for it.” You can completely understand where he’s coming from.

Lillard is about to turn 33 and is on the back end of the prime of his career. The clock's ticking, and the noise might be getting louder for a player so rooted in loyalty to the franchise that drafted him. The Blazers' front office is coming into the offseason with $25.7 million in cap space and a pillar growing impatient with their direction.

What’s a small market team to do in a conference built upon star power? Even the Sacramento Kings have found a way to figure things out! I was almost sure that Lillard was going to retire a Blazer. Despite many assertions on rings, nobody can take away from Lillard’s vast accolades – even if he doesn’t win one. But now I’m not so sure. Even a loyal player can start to see the writing on the wall, and the proverbial ball is in the court of the top of the Blazers organization. Rebuild or reload – choose your own adventure.