On The Mismatch podcast, Chris Vernon and David Jacoby discussed who the NBA's version of golfer Tommy Fleetwood is. In other words, who is a player that everyone would love to see win?
Jacoby had a controversial suggestion: Chris Paul in a Los Angeles Clippers jersey. But they ultimately came to the correct conclusion, going with a more universally beloved superstar in Portland Trail Blazers guard Damian Lillard.
Lillard has been more loyal to one single team than Paul. Despite his trade request and two seasons with the Milwaukee Bucks, only a handful of superstars around the league have had the same amount of loyalty and patience to a franchise.
Damian Lillard could be final piece to Portland's playoff puzzle
Vernon compared that dream hypothetical of Lillard winning to the feeling around the league when Dirk Nowitzki led the Dallas Mavericks to a ring over the Miami Heat superteam in 2011. It's hard to find more likable players than Dirk and Dame. The elephant in the room, and the difference between the two situations, is that it's unlikely Lillard will even be Portland's best player by the time he returns from injury.
Lillard is confident that he'll return to form, and we're not going to completely write him off after seeing his career trajectory going from Weber State to arguably the greatest Trail Blazer of all-time. But at the same time, we also have to be realistic about the situation. Unfortunately, history doesn't bode well for Lillard's return. Lillard is 35 years old, the same age as Kobe Bryant when he suffered his Achilles injury. Bryant never came back the same player, averaging roughly 20 points per game while shooting 38% from the field after.
The silver lining is that Lillard is joining a Blazers roster much better than the one he left two years ago. He doesn't need to be the best player to win a championship in Portland, and the timing of it all could work out well.
Lillard is expected to miss the entirety of the 2025-26 season as he continues to rehab. The Blazers' young core will be nearing their collective prime when Lillard is back on the court, making them a legitimate threat for a deep playoff run.
Not to mention, new owner Tom Dundon is set to take over before the 2026 offseason, when Portland will have significant cap space. This is the same owner who supposedly would have been trying to get Luka Doncic had he been the Blazers owner at the time of the blockbuster trade.
The internal improvements and potential external additions could align perfectly with Lillard's return. Portland's defensive-minded roster will still need Lillard's playmaking and floor spacing, making him a perfect fit.
Anything Lillard can provide to this Blazers roster should be considered a bonus, but he's also proved throughout his career not to count him out. Lillard still has something left in the tank, and it could be just the missing piece Portland needs to put them over the top, giving them a rare chance at a storybook ending.