Apr 22, 2025; Indianapolis, Indiana, USA; Milwaukee Bucks guard Damian Lillard (0) during game two of the first round for the 2024 NBA Playoffs against the Indiana Pacers at Gainbridge Fieldhouse. Mandatory Credit: Trevor Ruszkowski-Imagn Images Trevor Ruszkowski-Imagn Images

NBA Analyst Oddly Loops Miami Heat Into Scathing Damian Lillard Rant

Originally posted on Miami Heat on SI | By Jayden Armant | Last updated Jul 18, 2025 5:51 PM ET

Nine-time All-Star Damian Lillard heads back to the Portland Trail Blazers after a two-season tenure with the Milwaukee Bucks. His reach at championship glory elsewhere fell short after a disappointing chapter in Milwaukee.

And somehow, the Miami Heat are being brought into the Lillard situation. NBA analyst Kevin O'Connor used Miami's recent failure to fuel his argument that Lillard's best option was remaining with the Trail Blazers.

“The fact Dame's going back, maybe it had to happen this way for him to find out the grass isn't always greener," O'Connor said on his Yahoo Sports podcast. "He goes to Milwaukee, you feel like it's a championship situation, it's not. You wanted to go to Miami, that team has gone nowhere and is going nowhere. Then you find your way back in Portland after a traumatizing injury.”

“The fact Dame's going back, maybe it had to happen this way for him to find out the grass isn't always greener. He goes to Milwaukee, you feel like it's a championship situation, it's not. You wanted to go to Miami, that team has gone nowhere & is going nowhere” @KevinOConnorNBA pic.twitter.com/3DxIYnavDz
— Dru (@dru_star) July 18, 2025

The Heat were the heavy favorites to acquire Lillard two years ago after their 2023 Finals run. Falling short made it clear that they needed another superstar besides Jimmy Butler to be a bona fide contender. Lillard, who had long been loyal to the organization for years, finally expressed his desire to head elsewhere. He listed Miami as his preference, but the offseason stagnation created an opportunity for other suitors to bid. The Heat eventually lost Lillard to Milwaukee, adding another offseason failure in recent memory.

The Heat have won just one playoff game since then, and have generally underwhelmed in the absence of Jimmy Butler. Their lack of success may lay some claim to O'Connor's point.

Still, some argue that Lillard's presence would have at least slightly shifted Miami's postseason hopes.