Damian Lillard-Trail Blazers Partnership Nearing Moment of Truth

For four days, there has been an optimism within the Trail Blazers organization that drafting Scoot Henderson with the No. 3 overall pick on Thursday would not spell the end of Damian Lillard's time in Portland.

We should be finding out very soon if that hope is misplaced. On Monday afternoon, Lillard and his agent, Aaron Goodwin, were slated to meet with general manager Joe Cronin to discuss the direction of the roster going forward. Coming out of that meeting, there will either be an understanding that upgrades are coming or, if they decide there's no path forward, a trade request, which may or may not become public before a deal is done.

After the final game of the regular season, Lillard said Shaedon Sharpe was "enough 19-year-old" and he had no interest in being a part of the Blazers going young. On draft night, after taking Henderson and two other rookies and making no trades, Cronin insisted that he had "zero desire" to trade Lillard and that his goal was still to use trades and free agency to add veterans and put a "high-end winner" around him.

These two stances are not compatible. In order for the partnership to continue as both sides said they wanted, one outcome had to happen. The other one did. It's not a surprise that we're here, if you've been paying attention.

If Lillard does request a trade, it is expected that in the coming days and weeks, Cronin will work with Lillard's representation to find a deal that works for everyone. None of the options are great, but neither would be letting this drag out even longer if it finally reaches a breaking point. If this is the direction the Blazers are going to go, they've got a rebuild to start.

From both the Blazers' and Lillard's ends, the way they've handled the past month is totally understandable and perfectly defensible.

Lillard's media tour since the end of the season featured repeated hints that if Cronin didn't make a major move to upgrade the roster, it could change his stance on wanting to play his entire career in Portland. Applying that kind of public pressure to their teams' front offices is what star players can and should do in the modern landscape of the league. Lillard has never really exercised that leverage before, and being the good guy for the past 11 years didn't yield the results he wanted from either the current or previous front-office regimes. He had nothing to lose in finally trying the LeBron approach.

And Cronin's job, for whatever his public proclamations were about wanting to exhaust all options to build around Lillard, is to look out for the best interests of the franchise. In a way, moving up to No. 3 in the lottery in this particular draft hurt the goal of trading for an impact player. Once the Blazers' pick was high enough to land Henderson, believed by most draft analysts to be a franchise-level point guard who would go No. 1 in most non-Victor Wembanyama drafts, there were very few players it would have been possible to justify trading it for.

It's hard to blame Cronin for not making a deal with the third pick when the options that were out there would have set the franchise back in a major way. It's also hard to blame Lillard for feeling like he's Brett Favre and the Blazers just drafted Aaron Rodgers.

It remains to be seen where Lillard winds up should he end up asking out. The two destinations that have come up regularly are Brooklyn and Miami due to his close friendships with Mikal Bridges and Bam Adebayo. Neither has a great package to offer the Blazers, but if forced to choose, the Nets' collection of draft picks, both their own and Phoenix's, would seem more appealing. A Heat package centered around Tyler Herro (on a huge contract playing a position redundant with the young core Portland would be rebuilding around) and two mediocre far-out picks is an unmakeable deal, to the point that Cronin taking it would be just as irresponsible as trading the third pick for a non-superstar would have been.

Wherever Lillard goes, you just hope he will have made the decision for himself. Once he's out of Portland, he'll no longer be a full-time content vertical on First Take. The talking heads that have been trying to push him in this direction for four years out of a supposed concern for the well-being of his career will immediately move on to "rescuing" the next star from small-market irrelevance. And if he doesn't win at the level he wants to in a couple of years, it's not hard to envision his career taking the Chris Paul-Russell Westbrook trajectory of becoming a big salary to dump every year. That's a risk superstars run when they leave their original teams in the current age of player movement. If that's a gamble he's willing to make, more power to him.

Life after this marriage ends may not be better for Lillard and it definitely won't be better for the Blazers. Things would be rough in Portland for a while, and there's no guarantee the future will be brighter.

There are worse places to start with a rebuild than what they have. Sharpe showed legitimate star potential down the stretch of his rookie season, and everything I've read and watched about Henderson over the past week makes me convinced he has what it takes to be a franchise-changing superstar on and off the court.

But neither of them are going to get to that level for a couple of years at least. There will be a lot of losing in the meantime. The segment of the fanbase that wanted this might not be fully prepared for what they're signing up for.

If this is the end, both sides will be making a bet that they'll be better off without each other, and it's far from a sure thing it will pay off in either direction. Lillard had better hope he's right, that doing this will get him the championship Portland was never able to deliver for him. And Cronin had better hope he's right, that Henderson is good enough to make what will be a painful summer worth it.