Blazers’ Damian Lillard deserved to ask out, but Joe Cronin isn’t to blame

Two seasons ago, the Portland Trail Blazers’ descent down the Western Conference standings ended any chance of Damian Lillard returning from an abdominal injury. Last season, the team shut down Lillard after a chance at a high lottery pick took priority over a low-level playoff seed.

That’s two years of Lillard’s prime the Blazers have spent tanking and hinting that lottery picks could be traded for win-now veterans, only to end up drafting two rookies.

This offseason, most people perceived Portland General Manager Joe Cronin’s draft-day decision as a binary path: trade for a veteran to win now, or draft a rookie to win in the future. An evaluation of Cronin’s options shows that case was not so straightforward.

Blazers GM Joe Cronin is not to blame for Damian Lillard’s trade request

The expectation after last season was that the Blazers would strongly consider moving their lottery pick for a veteran, as Jason Quick of The Athletic reported. After Portland obtained the third pick in the draft, Cronin confirmed the team’s plan to be aggressive in trade talks.

What emerged in the trade market was an underwhelming group of floor-raisers, not needle-movers.

Cronin has received frequent criticism for his messaging. His press conference comments – particularly those delivered at the end of last season – signaling the team’s willingness to sacrifice its future for the remainder of Lillard’s prime, have come across as misleading.

Drafting Scoot Henderson, counterintuitively, aligns with the core of Cronin’s messaging that’s remained consistent throughout his tenure: build a championship-level contender around Dame.

When he replaced former GM Neil Olshey, Cronin inherited a playoff-level team. Around Lillard and CJ McCollum, Larry Nance Jr., Robert Covington and Norman Powell rounded out a solid core – one capable of making some noise in the early playoff rounds but not talented enough to win at the highest level.

Raising the Blazers’ ceiling to championship heights was the logic behind the McCollum trade. A Dame-CJ backcourt works if a team has playoff aspirations, but their combined defensive liabilities limit championship upside, given the defensive demands of playoff basketball.

Saddled by hefty contracts and limited flexibility, Cronin devised a plan: reshuffle the whole deck. Open up lots of flexibility and use it to acquire upside. Take big swings. Not all of them will pan out, but just one or two hitting might provide avenues toward championship contention.

Shaedon Sharpe was a big swing. No player available for the seventh pick in the 2022 draft presented the same amount of upside.

Trading for Jerami Grant wasn’t as much of a gamble, but it’s far easier to envision him as part of a championship-level core with Dame than McCollum due to positional fit.

After trading away Josh Hart and Gary Payton II at the 2023 trade deadline, Cronin’s biggest PR mistake was doubling down on the team’s commitment to prioritizing the present over the future. This offseason’s draft contradicted that commitment, at least on the surface. But Cronin’s actions since the deadline have remained consistent with his philosophy of taking big swings.

Which players were actually available in a trade for the 2023 draft’s No. 3 pick remains unclear. At best, they included one of Pascal Siakam or OG Anunoby, whatever collection of assets with which the Pelicans were willing to part to draft Scoot, and maybe Mikal Bridges if the Blazers were willing to pile more assets on top of the third pick.

Siakam, Anunoby and Bridges are good players, but none of them move the needle for Portland on their own, and acquiring any of them would have required the organization to empty its chest of assets. A hypothetical core of Lillard, Siakam and Grant is an upgrade from any group Olshey assembled, but relative to the rest of the talent in the Western Conference, it still won’t get the job done.

More moves would be needed – a problem when trading for Siakam would have exhausted most of the team’s valuable trade assets.

Drafting Scoot Henderson gives the Blazers a chance to acquire a superstar

Scoot changes the equation. No, he won’t help Lillard contend for a title in his rookie year, but there’s still a chance he pops. If the Pelicans’ reported aggression to move up the draft board for him was any indication, the league views Scoot as someone with star-level upside.

He’s 19 years old and on a rookie-scale contract. In other words, his value keeps trades for superstar-level players in play for the Blazers.

This summer has re-emphasized that the league is constantly in flux. The balance of talent throughout the NBA  is constantly changing, meaning it’s only a matter of time before the next superstar feels alienated on a team, signaling that a different direction is coming.

After years of the Philadelphia 76ers trying to find a second star to pair with Joel Embiid, James Harden is unhappy and Embiid has sent mixed messages about his commitment to the 76ers’ organization.

The Milwaukee Bucks almost lost their defensive anchor in Brook Lopez this summer. Even though they re-signed Lopez, Giannis Antetokounmpo’s future seems hazy in Milwaukee. The core around him is aging, and the team has minimal flexibility to keep leveling up.

A recent interview in which Giannis affirmed his willingness to leave Milwaukee if a “better situation” for him to win opens up adds to the intrigue.

Even if Giannis and Embiid stay put, there’s no telling which superstar is next to ask out. That’s the nature of the NBA.

Trading the third pick for a middling all-star would have burned the Blazers’ collection of assets. Drafting Scoot keeps alive the possibility of trading for the next needle-moving superstar.

Lillard and Siakam have a chance at making some noise in the second round. Lillard and Giannis? That’s a championship-level duo.

Now that Dame’s trade request has already been made, he will likely be moved, and the Blazers will rebuild around Henderson. That’s not a bad thing. Henderson has generational upside. His arrival deserves to be celebrated, not clouded by trade talk and fans’ anger.

Cronin’s messaging wasn’t perfect. But he was right to keep taking big swings. Moving the third pick for a vet would have left the Blazers right back where they were at the end of the Olshey tenure: not enough talent to win at the highest level and not enough flexibility to keep building.

Big swings deliver championships. Low-upside moves do not.