Damian Lillard's playoff heroics are legendary in the NBA universe, but they have yet to lead to a ring. The Portland Trail Blazers have ran into an unfortunate combination of untimely injuries and super teams over the last few seasons, despite Lillard cementing himself as a top-15 player in the league with a quality running mate in C.J. McCollum.
Lillard is firmly dedicated to staying in Portland. He's made that clear in numerous public statements and when he signed a four-year supermax extension with the Blazers last summer. That deal will keep him in the Pacific Northwest through 2025. Despite Dame's love for Portland, Stephen A. Smith believes he must leave the Trail Blazers if he ever wants a chance at a ring, as discussed on First Take today:
The first half of Smith's argument has a solid foundation in logic. The league today is centered around elite two-way players. Of the five best players in the NBA right now (LeBron James, Kawhi Leonard, Giannis Antetokounmpo, Kevin Durant, and Stephen Curry) four possess elite offensive and defensive traits. Lillard and McCollum, while excellent offensively, can't be both the No. 1 option and guard the opposing team's best player. They don't need to be able to do that to have success, but it's much harder to win a title when there isn't an overlap between a team's best offensive and defensive players.
Unfortunately for Lillard, fate has aligned in such a way that winning a championship in the next five years will require a remarkable amount of luck for Portland. James and Leonard both headed to the Western Conference just as the Warriors' dynasty was dying. Unless injuries strike the Lakers and Clippers, there will always be a difficult road to the NBA Finals. Lillard can catch fire like no one else, but unless Portland can acquire players to guard the elite wings that populate the conference, the team will be hard-pressed to beat the best of the best in a seven-game series.
The second half of Smith's point is where he loses me. He suggests the Knicks and the Lakers as two possible alternatives. While Smith admits his bias when it comes to the Knicks, I would argue there is no destination in the NBA that would decrease Lillard's title chances more than that particular organization. The Lakers cannot acquire Lillard, no matter what kind of cap gymnastics they could perform, until LeBron is nearly 40.
All in all, Smith is probably right. Portland's options for potential acquisitions are limited with its cap sheet. There's no way for the Blazers to substantially improve unless they trade McCollum, which they won't do without Lillard's sign-off -- and, from what we've seen, he isn't particularly likely to do that.
Championship heights could be reached if Lilliard somehow ended up in the Eastern Conference and only had one very good team in the Bucks and the injury-prone duo of Durant and Kyrie Irving to go through. Once the Finals start, all bets are off, no matter who Lillard might face off against.
But he won't do that, and I'm glad for it. Lillard is a blast to watch, and sports is about watching a great player like him struggle to reach that mountaintop over and over again. If he never reaches it, that's too bad. But his greatness is still undeniable. And if he does, well, it makes for one of basketball's greatest tales.