Blazers benefit on Draft Night, but have fewer chips to "push in"

Joe Cronin didn't lose all his trade chips. But "threading the needle" is harder than ever.

It’s the best of times. It’s the worst of times. The Blazers won. But it feels like they lost. I feel like Rosie Perez in White Men Can’t Jump (1992).

For the past three weeks, it seemed like the Portland Trail Blazers making the No. 3 pick would be the last straw on Damian Lillard’s tenure sight unseen. And perhaps, one day, maybe it still will be. Which is the feeling hanging over the franchise after what normally would be a completely celebratory moment.

Michael Jordan, in his final act as the controlling owner of the Charlotte Hornets, gave us a piece of dramatic symmetry nearly 40 years since Portland passed on taking the GOAT No. 2 in the 1984 NBA Draft, by passing up on the player Portland actually wanted with the No. 3 pick, delivering Scoot Henderson to Portland. The bar I was at during the draft was as excited as I’ve seen it around here since they made the Conference Finals.

A few weeks ago, naive as it may have sounded to some living outside my own brain, I hypothesized a basketball world in which Damian Lillard, Scoot Henderson, and Shaedon Sharpe were on the same team. Two of the three are amazing at getting to the rim. Two of the three are elite shooters from deep. And Henderson is probably already the best defender of the three. And while in my basketball convictions, I still believe such a pairing would be a problem for opposing defenses, I know my basketball proclivities have little impact on such things.

The Brooklyn Nets refused to play ball for a trade involving Henderson and Anfernee Simons for Mikal Bridges, it seems less because of the value, but more because they believe they can get Dame. When it comes to Brooklyn or Miami, the Nets have far more attractive draft capital, as well as an exciting frontcourt player in Nicolas Claxton, which remains this team’s biggest need. However, seeing Brooklyn enter the season having made no moves, only to bring back the same sub-.500 team that they had after the trade deadline would be very satisfying when they had a shot to bring a potential superstar in a deal that would have benefitted both teams. Now I only want bad things for the Brooklyn Nets, a branding exercise disguised as a basketball team, that the NBA has tried to make happen for two decades, only to fail.

As far as Miami is concerned, would Portland really be enticed to take a deal bringing back the ball-dominant Tyler Herro to take touches away from Scoot/Sharpe/Simons? And while I like Philadelphia’s Tyrese Maxey more as a prospect than I like Herro, the same question about bringing back another small guard remains.

And with regards to Lillard, how much does he think it would really work playing next to James Harden, as it seems more likely now that Harden stays in Philadelphia? How about the Knicks next to Jalen Brunson? Another small guard? Not to mention, I’m super passing on a package involving RJ Barrett, Julius Randle, and picks.

Erik Spoelstra being the coach in Miami is probably the ultimate variable in their favor. But the business of the NBA ecosystem is set to come down on Miami too. Also, Erik Spoelstra is set to get a new contract soon. Is Mickey Arison going to pay him $20 million per year, which he will almost certainly ask for after Monty Williams landed his massive deal in Detroit? They also are set to lose starting wing Max Strus in free agency, because he’s about to get paid. Caleb Martin has a player option next summer that he will almost certainly pass on after his fantastic playoff. And while the Heat just made the Finals (we will ignore that Giannis got injured), does Dame really need to move his entire life in order to come up short against Denver?

These are the questions at hand for the Blazers and for Lillard. And I don’t think anybody involved has a clear answer about what’s best for both. One thing that is clear to me is, for Portland, trading Lillard is not what’s best for the franchise, because the potential returns on the market are so minimal and do not complement their young core. However, after months of rhetoric about “pushing their chips in,” the Blazers have considerably fewer chips to play with at the poker table to add more veteran help they need to field a playoff team around Lillard.

Intellectually, after sobering up from last night, I agree that adding Scoot is better than adding a star player who is older and more injured. Especially in a world with an even more restrictive collective bargaining agreement. But these are complex, business, personal, and emotional decisions. I do not envy Cronin or Dame’s positions. Although it does look like Dame is having a great time in Paris with family and Jerami Grant. That part, I do envy.

But how will Joe Cronin and the front office answer their questions? Last night, Cronin said the “biggest possible move” was drafting Henderson. And as a generational talent, maybe that’s true. But now the Blazers have four guards on the roster who are going to demand around 30 minutes per game with only 96 minutes between the two guard spots.

I do believe the Blazers looked around for what they could get at the draft and I understand why they kept Scoot. Paul George’s shoulders and knees have been through a lot. It also seems that New Orleans never wanted Scoot Henderson as much as they had projected in the past few weeks and that Zion Williamson, as nice as that would be, was never truly on the table.

But now it’s on Cronin and the rest of the front office to find players who can actually create a roster with a chance at the postseason. Not only to convince Dame that sticking around isn’t a waste of time, but they need to get their young dogs some playoff reps ASAP if they want to do anything beyond being a fun, plucky team.

Lillard can’t be traded until July 9, which is giving Cronin time to keep this thing going. But make no mistake, more than at any time since two summers ago, it feels like the clock on Dame Time is actually on a countdown.