Scoot Henderson is a Blazer. So is Damian Lillard, who made All-NBA last season, plays the same position as Henderson, and is 14 years older than him. These contradictions are either a weird problem or a tremendous opportunity, depending on your perspective.
There are two forces here, pulling in opposite directions: If you have an All-NBA guy, someone with multiple series-ending walk-offs, you should try and win; if you stumble upon someone considered by GMs to be a No.-1 level prospect, the sort of player with the potential to anchor a franchise for a decade-plus, you should build around him. While odd roster-timeline questions are endemic to the messy business of team-building, nobody's range of outcomes is as wide as Portland's is right now. They could try to win 16 games next season, or they could try to win 60, and whichever path they choose, it could shake the league.
The inflated stars-for-picks trade market has made committing to winning in the short term come at a prohibitive price. There are the teams with draft capital deficits and stars (Cleveland, both L.A. teams, Phoenix, to name a few), there are the teams with nutty draft pick surpluses and young players (Utah, San Antonio, Oklahoma City), and there are a ton of teams in between. Though results are necessarily going to skew across the board, most franchises have decided whether they want to win next season and how much future potentiality they are willing to leverage to do so. The Blazers can't expect too much with their current roster, and the bizarre three-way fit between Lillard, Henderson, and Anfernee Simons means they will have to do something this offseason.
For two years now, Lillard has fielded increasingly tiresome questions about his legacy and whether he would ever want to leave the Blazers for an actual contender. The whole saga has been a boring slog, though he's actually started lobbying for the Blazers to mortgage the future and get him some help.
"It ain't a threat. I ain't gonna say I'm putting them on the clock. I'm just saying if those things can't be done—if we can't do something significant like that—then we won't have a chance to compete on that level," Lillard said of trading out his teenage teammates for veterans in April. "And then, not only will I have a decision to make, but I think the organization will, too. Because at that point, it's like, 'Are you gonna go young, or are we gonna get something done?' I think we just kinda been on the fence with fully committing to either one."
I feel for Lillard here, and I admire his candor in openly naming the contradiction. Not only has he stuck with Portland through some tough times, he's now entering his late prime with a bunch of extremely raw prospects on his team. He has always wanted to win in Portland, but it's not possible to do so with Henderson and Shaedon Sharpe still at the start of their development curves. "There’s other stuff to do here,” Blazers GM Joe Cronin said. "I feel like we’ve done a good job of putting ourselves in good position to make these moves and start to get aggressive and push our chips in." To me, that is as direct of an admission that someone is getting traded as you will see from an NBA GM, and I can't shake the feeling that Lillard is going to ask out soon. Cronin said he and Lillard hadn't talked since Tuesday, and the tone of reporting from Lillard's official stenographer, Chris Haynes, is inching ever closer to openly adversarial.
Sharpe and Henderson are two hyperathletic geniuses, the sort any rebuilding team would be thrilled to get the chance to build around. Lillard will assuredly fetch a huge bundle of stuff should he actually get traded, though as Blazers fans themselves could tell you, rebuilding around hypothetical talent is not guaranteed to work out. There's no guarantee that either player will ever turn out to be half as good as Lillard, and as tempting as the new shiny thing can be, committing to the youth movement is just as risky as going all-in on a soon-to-be 33-year-old. That's what makes this position so fascinating: there is no safe option. The Blazers are going to have to fling themselves into the unknown.
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