With The Clock Having Run Out On Dame Time, Now What?

Here we’ve been, skipping along through the Trail Blazers’ offseason, using a roadmap as our guide (https://oregonsportsnews.com/the-dame-dilemma-to-trade-or-not-to-trade-that-is-the-question/), seemingly everything going according to plan, only to find ourselves in a tangled pileup on I-5. Or so it feels, with Damian Lillard having requested a trade to the Miami Heat!

We even made it as far as Step 3 on our MapQuest with the resigning Jerami Grant, only to have Dame make his request in the immediate aftermath. It’s almost as if Lillard was simply waiting for his friend and teammate Grant to get his bag before semi-demanding a trade. (By the way, a trade is less a request and more of a demand when you insist on being traded to a single team, I’m just saying.) While the timing of Dame’s demand is curious at best and super suss at worst, this is not the story I’m interested in telling.

As we’ve learned from the wreckage wrought by this pileup, this offseason journey we’re on as Blazer fans is more fluid than anything. And thank goodness for this! Otherwise, we might have taken an unnecessary detour by completing the steps on our road trip in order by trading Anfernee Simons (Step 2).

With Lillard exiting stage left (eventually), Simons very likely will be Portland’s’ best player next season, even with the drafting of Scoot Henderson, the resigning of Jerami Grant to his exorbitant contract ($160M over five years), and the anticipated emergence of Shaedon Sharpe. He’s that good! Or so I think he’ll be when not paired with Dame and his crazy high usage.

It’s Penny Time, as in Anfernee, but not Hardaway!

Admittedly, this doesn’t have the ring to it that Dame Time does, but this catchphrase is a euphemism of sorts as it’s a work in progress, much like our beloved Portland Trail Blazers. And speaking of work, Joe Cronin certainly has his cut out for him now.

But it’s in Mr. Nice Guy I’m hoping to trust forevermore (https://oregonsportsnews.com/with-the-future-secured-now-what-should-the-portland-trail-blazers-do/), even though, at least according to Jason Quick of the Athletic, he had zero competition for the job:

“Jody Allen promoted Cronin to replace Neil Olshey without interviewing a single candidate. Not one.” (https://theathletic.com/4643433/2023/06/27/damian-lillard-trail-blazers-future/, subscription required).

I won’t hold this against him, provided he can maximize his return for Lillard. And given the game of chicken, hardball, or whatever you want to call it, he’s playing presently with Dame and his agent, he’s off to a good start!

If necessary, I would love to see Joe take a page from another Joe’s playbook. The other Joe being Joe Tsai, the owner of the Brooklyn Nets, and, by extension, his General Manager, Sean Marks. When given an ultimatum by his star player at the time, Kevin Durant, to choose between him and Head Coach Steve Nash and GM Marks, Tsai took to Twitter:

“Our front office and coaching staff have my support. We will make decisions in the best interest of the Brooklyn Nets.”


Trading Durant at that time for what likely would’ve been pennies on the dollar was not “in the best interest of the Brooklyn Nets,” so they brought KD back the following season (2022-23), then traded him to the Phoenix Suns in the lead up to that season’s trade deadline for a premium return more commensurate with a player of Durant’s caliber.

This is how far I’m hoping our Joe is willing to take this, even if it means bringing an unhappy Damian Lillard back for next season. Getting this right is that important! Which, thankfully, is a point on which Woj and I concur:

“This is the trade of Joe Cronin’s NBA life. It doesn’t have to go quickly, but it does have to go right.”

(https://www.espn.com/nba/insider/insider/story/_/id/37964651/inside-trail-blazers-damian-lillard-trade-talks, subscription required)

Where there may be a divergence between Woj and I lies in how we define such a trade as “go[ing) right.”

A trade that meets this definition for me may already be on the table in some form, but this is just me reading the tea leaves. A Woj I am not, to be precise.

Now onto the trade and the ‘now what’ post-Dame’s trade demand.

While the rest of the NBA may have, I can’t seem to quit you, Ben Simmons!

During OSN’s Summer Break, I got my Twitter on with a series of Tweets to explain why trading for Simmons makes sense.

“Ben Simmons very well could be a sunk cost for any team that may acquire him, but pre-yips/injury, he was a rising All-NBA & All-Defensive Team player. In the right situation, playing to his strengths & for a coach fully vested in him, I still believe he could return to form.

“And if any NBA coach can bring the best out in Simmons, it’s Chauncey Billups! A return to total health willing, Billups, once a bit of a sunk cost himself, could lead Simmons down Redemption Road.

“But given Simmons IS a sunk cost for the Nets presently, Brooklyn likely would gladly take Tyler Herro & Duncan Robinson off Miami’s hands as the 3rd team in a trade for Damian Lillard. And send Noah Clowney to Portland for their trouble.

“And if I’m the Blazers, I would also want Nikola Jovic from Heat & possibly Jaime Jacquez Jr., along with all the future 1st round picks I could squeeze out of Miami & Brooklyn.

“This, to me, is a trade that represents the best nod to present & future competitiveness should Simmons return to full health. In Billups, I would absolutely trust in this redemptive endeavor! And the risk is mitigated by Simmons only having two years left on his mega-deal, and by the haul of young players and future draft picks, this trade would net Portland.

“So, for those keeping score at home…

“The Blazers receive:

– Ben Simmons & Noah Clowney from the Nets -&-

– Nikola Jovic & possibly Jaime Jacquez Jr. from the Heat

– Plus, 1st round picks from one or both teams

“Brooklyn receives:

– Tyler Herro & Duncan Robinson from Miami

“The Heat receive Damian Lillard.”


I would also add that Simmons is the rare player that can play the 1 – 5, given his size, strength, and skill. Before you scoff at the idea of a non-shooter playing shooting guard, think Tony Allen, but with elite play-making ability.

And with Simmons joining a starting five likely consisting of Simons, Sharpe, Grant, and the Bosnian Beast, there would not be a non-shooter among his starting mates, giving Simmons all the room he would need to thrive. 

I rest my case …

… or have I?

P.S.  For those of you who may be concerned about the effect trading for Ben Simmons would have on Scoot Henderson and his development, you needn’t worry!

After graduating early and skipping his senior season of high school, so at the tender age of 17, he burst onto the scene in his first year with the G-League’s Ignite with averages of 14.3 pts, 4.8 reb, 4.2 ast, & 1.67 stl.

Relevant for our purposes because: “In his first season, Henderson was the junior partner on a team that featured 2022 draft picks Dyson Daniels (No. 8 to the Pelicans), MarJon Beauchamp (24th to Milwaukee) and Jaden Hardy (taken in the second round, No. 37, by Dallas). Henderson wasn’t on the ball most of the time, Daniels was. Henderson was given the green light to play and not think.”  This all per some obviously stellar reporting from The Athletic’s David Aldridge.

(https://theathletic.com/4676386/2023/07/17/scoot-henderson-blazers-point-guard-billups-brooks-curry/, subscription required)

The point is, I am all but convinced Scoot To My Lou is a transcendent player, and he will have a high impact on the ball or off, as a starter or reserve.  He won’t be limited, not really.  He, too, is that good!

P.S.S.  In the context of his trade, I am also very open to him starting alongside Anfernee “Penny” Simons.  Let him and Shaedon Sharpe battle it out for the right to start.  Either would make for phenomenal 6th men.  I don’t think it’s even out of the realm of possibilities that Henderson or Sharpe could be the 6th man of the year.  They’re both that good!

By now, though, I think you catch my drift!

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About Jason Poulsen 11 Articles
As a former collegiate basketball player, with a great deal of emphasis on the former, my passion for the game has since led me on quite the journey. Writing for the Oregon Sports News, along with the effort I’m putting in to finally get a long ago developed proprietary basketball performance analytical tool off the ground, represent full circle moments. There have been a multitude of stops & roles along the way, the pertinent ones being Assistant to Director of Basketball Operations, Basketball Operations Assistant, NBA Draft Statistical Analyst, & Sports Writer, & the less pertinent – Store Manager, Lids Sports Group. I suppose one hasn’t really lived unless they’ve worked in retail or so I’ve told myself.