Portland Trail Blazers: How big is Damian Lillard’s championship window?

Damian Lillard is firmly in his prime at 29. Sooner rather than later though, the Portland Trail Blazers need to contend with him. How long do they have?

Damian Lillard was drafted in 2012 by the Portland Trail Blazers, and since, has made the playoffs 6 times, won 4 playoff series and recently enjoyed a trip to the Western Conference Finals.

However, Lillard is now 29 years of age, and with the Blazers likely missing the playoffs this season, Portland need to do all they can if they want to give Lillard the chance at a championship. Granted, this season hasn’t been as bad as it looks (injuries have taken their toll), but the question stands: how long does Lillard have to win a championship as the #1 guy, and is this roster good enough to do that?

I’ll start with the roster. If we remove any extravagant offseason moves, which are unlikely anyway, then the Blazers will be opening up the 20/21 season with a starting 5 of Lillard, McCollum, Ariza, Collins and Nurkic.

Rodney Hood may not be ready to start from the get-go then, and it is still unclear whether Portland will be bringing Carmelo Anthony back.

The bench will most likely consist of Gary Trent Jr, Anfernee Simons, Nassir Little, with Melo and  Hassan Whiteside currently questionable. The Blazers will also likely sign one free agent, draft a top 15 pick, and if Whiteside or Melo do move on, potentially make a low-risk trade as well.

So is this roster good enough to challenge the league’s best? The Blazers went to the Western Conference finals with the same back-court, and Al-Farouq Amuinu, Maurice Harkless (who could be available on the cheap this summer) and Enes Kanter in the front-court.

In my opinion, the potential roster next year is more talented, and Ariza and Collins match up as pretty equal defenders when compared to Aminu and Harkless.

The bench was a huge factor as well; Seth Curry, Evan Turner, Meyers Leonard, Jake Layman and Zach Collins combined scoring, experience and some terrific chemistry to form one of the best second units in the league (Video below shows the bench combining for 58 vs the Raptors). Next season’s bench definitely needs some veteran leadership, and the move in free agency could be to chase a back-up point guard.

We could also suggest a move for some front-court scoring, but the options are pretty thin around the league, and unless the Blazers want to try and package Whiteside in some sort of sign and trade, they don’t have much to trade either.

The wing position is still an area of weakness, but Ariza can score the ball much better than either Aminu or Harkless ever could, and plus, Jusuf Nurkic will be back. I believe the Bosnian is Portland’s second best player, and he was sorely missed in the WCF. Nurkic will feel like a new addition when he eventually returns.

So the roster doesn’t need any major changes; a few shrewd pick-ups should give the Blazers the personnel to at least challenge for a Finals spot. If we predict that the core of this roster will stay together for the next few years, then how many attempts do Portland and Lillard realistically have of winning it all?

In the last 20 years, only three guards have been been the #1 option on a championship team; Kobe Bryant in 2009 and 2010, Dwayne Wade in 2006, and Steph Curry in 2015. Allen Iverson probably went furthest with the least amount of help, back in 2001 when he dragged the 76ers to the Finals.

Winning a championship with a guard as your best player can be done, but it’s tricky. This doesn’t mean it’s out of the question for the Blazers, but it does mean time is running out. Lillard will have to be at the absolute peak of his powers for Portland to go all the way, and at 29, he probably only has a few years left.

I tried to find a sensible comparison for Lillard, but it was difficult, as there’s never really been a player quite like him. Iverson seemed to fit the best, a quick guard who shouldered the main load of the team for a long time. For Iverson, he probably fell off around 32/33, when he was traded to the Denver Nuggets. He wasn’t useless, but he struggled with injuries, and his points per game dropped down to 24.

Dame relies heavily on his quick step, and his athletic ability and shiftiness around the rim. Likelihood is, he’ll lose that quickness around 33-35, and won’t be able to lead a team all the way through a postseason.

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He’ll always have his long-range jumpers, but it won’t have the same effect without his speed. Lillard’s absurd right to left and first step creates a ton of space for his three-pointers, as defenders have to give him respect both when driving or stepping back.

Dame will be 30 heading into the 20/21 season, and I think it’s realistic to say Portland have around three seasons left to maximise Lillard’s potential.

If Nurkic and McCollum stick around, they bolster their wing positions and add a bit of experience, then Portland can definitely win with what they’ve got. Whether Dame’s age will force the Blazers into riskier moves down the line, we don’t know, but we do know that the clock is ticking, and Portland must get it right.