The Trail Blazers are at a fork in the road.


Are they flexible enough to keep one foot on both paths in front of them until they converge again in the future? Or will trying to do so tear them apart?

Can the team contend in the Western Conference?

When you have a player as good as Damian Lillard, the tendency is to always view yourself as a contender. After all, in the 8 seasons before this one where Lillard was injured, the team’s average record was 47-35 and they made the playoffs every year. But were they contenders? In 5 of those 8 years, the Blazers were eliminated in the first round. The one time they made it as far as the conference finals, they were swept by an undermanned Warriors team. They went 22-40 in the playoffs over that stretch, winning only 4 of 12 series. When you make the playoffs year after year and you have a superstar there’s a tendency to think that you’re one piece away, when you’re really not that close at all. In reality, you’ve maxed out as a second-tier playoff team who will open on the road and occasionally draw a favorable matchup and sneak into the 2nd round. And this newly remade Blazers team is even further away after trading veterans CJ McCollum, Larry Nance Jr., Norman Powell, and Robert Covington. Unlike in previous years when the team moved on from veterans such as LaMarcus Aldridge, Nic Batum, Wesley Matthews, Robin Lopez, Steve Blake, Chris Kaman, Ed Davis, Evan Turner, Al-Farouq Aminu, and Carmelo Anthony, this time those experienced players were replaced by young unproven players. But besides Anfernee Simons, who carried the team when Lillard was out injured by averaging 23.4 ppg and 5.8 apg and shooting over 42% from three point range over 27 games, none of the others even established themselves as reliable starters.

Considering this, it seems like a long climb back to contention and yet the team surely feels some pressure to accelerate that process too appease Lillard, who at this point in his career can’t afford to throw away 2-3 of whatever seasons remain of his prime on a rebuild. But that mindset is dangerous; it’s exactly the kind of thinking that has the team forfeiting future assets for a veteran like Jerami Grant, who is an upgrade but won’t exactly vault the team up in the standings. It’s unclear if the team will be able to retain starting center Jusuf Nurkic, who is an unrestricted free agent; even if we assume that Nurkic stays put, the team’s starting lineup of Lillard, Simons, Josh Hart, Grant, and Nurkic is fairly underwhelming. Add to that an inconsistent and inexperienced bench brigade of Justise Winslow, Didi Louzada, Nassir Little, Trendon Watford, Greg Brown, Keon Johnson, and lottery pick Shaedon Sharpe, and it’s difficult to imagine the Blazers having any shot at a playoff berth. The Suns, Grizzlies, Warriors, Mavericks, and Nuggets aren’t going anywhere, barring catastrophic injuries. Kawhi Leonard is returning to the Clippers and Zion Williamson is returning to the Pelicans. The Lakers still have Anthony Davis and LeBron James. The Timberwolves won 46 games last year despite 6 of their top 7 players being age 26 or younger.

Like it or not, the Blazers are in a rebuild. But is it possible that deep down, they already know this? And that moves like the one for Grant are really just a way to buy time? If the team went into an obvious and immediate rebuild, Lillard might demand a trade. But if the team can win enough games and generally be competitive, Lillard might be appeased long enough for the young core to develop. Unfortunately there’s a paradox – how do you give the young talent enough game experience to develop while still having enough minutes the veterans to stay engaged and ensure they’ll be competitive and win some games?

Two words – Shaedon Sharpe.

The Blazers selected Sharpe with the 7th pick. They could have traded that pick for another veteran, to fully commit to the effort to return to playoff contention. Or they could have take a safer prospect who may have been more guaranteed to help immediately as a rotation player. But the Blazers are trying to serve two masters. And in Sharpe they saw an opportunity to take a player they viewed as a generational talent, one who might have been in contention for the top pick had he played college basketball. Those opportunities don’t come along very often. Despite his age, if Sharpe really were one of those unique talents it would be evident pretty quickly. If all of a sudden Lillard had a legitimate wingman and a player as good as Simons was now the third best player, that would change everyone’s outlook. It would also make the team a desirable free agent destination for talented big men.

What evidence is there that the Blazers held Sharpe in such high regard, and that they felt that he could help them walk this tightrope? Some clues can be found in comments made by recently hired Assistant GM Mike Schmitz before he joined the organization. Until May, Schmitz had been working as a draft analyst for ESPN, where over the past few years he’d put built up quite a portfolio of skillfully produced video scouting summaries and detailed film breakdowns and interviews with top prospects.

Regarding Sharpe, Schmitz made the following assessments:
– “There’s a real argument to be made that he’s the best perimeter prospect in this 2022 class.”
– “It will be incredibly difficult for teams who have seen him in person to pass on his combination of physical tools and talent on the perimeter.”
– “Sharpe is as smooth and skilled of a scorer as Paul George with the potential to develop into a reliable playmaker and defender.”
– “Sharpe, unlike some of the other top prospects, has the ability to create offense on three level: he can make pull-up 3s with range, can create space out of isolations, and can get all the way to the rim for explosive finishes.”
– “In terms of the potential as a pick-and-roll scorer with passing upside, Sharpe is in a class of his own.”

Along with all of this effusive praise, Schmitz did acknowledge the risk. Sharpe is still a bit of a mystery due to his meteoric rise as a high school prospect and his reclassifying and subsequently missing a whole year of advanced competition. But the Blazers, for the first time in years, are a bit of a mystery themselves and the enigma at the center of it all is Lillard, who has a chance to be one of those rare superstars who spends his entire career with one franchise but also wants to win a championship. The franchise player ironically becoming the mirror image of his own team, each trying to walk two paths and hoping they converge. If they don’t, there will be a tough choice for someone to make and only one thing would be certain at that point – the Blazers will be losing a lot of basketball games.