The Dame Dilemma – To Trade Or Not To Trade, That Is The Question

I think I’ve made my points quite clear regarding what I believe the Trail Blazers should do this offseason. But with there always being room for interpretation, let’s recap, shall we:

As all such players are not created equal, there are three factors worthy of scrutinization: 1) the availability of them – the best of the best, aka the truest of the bonafide, likely aren’t coming to Portland [think Giannis Antetokounmpo, Devin Booker, Luka Doncic, Nikola Jokic, Jayson Tatum, Kevin Durant (after just being acquired by the Suns), Joel Embiid, LeBron James, Jimmy Butler, or even Anthony Davis]; 2) their fit size & skill-set wise (no smallish/point guards or defensively challenged players thank you very much); and 3) price point with 2 & 3 being “the” most important considerations.

In the case of Siakam, the cost of doing business with the Toronto Raptors is the biggest question. If the 3rd overall pick in the upcoming NBA draft or even Shaedon Sharpe are involved, then “I’m out like Buster Douglas!”  (

The single most important consideration with Draymond is Father Time. If he doesn’t exercise his player option for next season, I’m not sure I would pull the trigger on a trade for him. But not because I view Green as only a one-year rental. Should they acquire him, the Trail Blazers should resign him, but only at their price point. And even if the Blazers win the championship next season, this should not factor into this calculus.

As an aside, paying a player for past performance is always fraught with challenges. I can think of no greater example of this in the history of the Trail Blazers franchise than Brandon Roy, as great as he was.

[Not that he actually had anything to make up for, but Roy certainly paid Blazer Nation forward by being a good luck charm at the NBA Draft Lottery. So again, I say thanks, Brandon Roy!]

He was unquestionably amazing, an All-Time Great who will forever live in Blazer lore, just not for long enough, by no fault of his, by the way. The fault was the franchise’s by investing a max contract in a player with balky knees. Let’s just hope they’ve learned their lesson if they have a chance to trade for and then resign Draymond.

With this being said, provided he exercises his player option for next season, I still am all in on the Blazers trading for Green. Him and Lillard forming a lethal duo beyond next season is a bit sketchy, though. They will need even more help going forward in their pursuit of bringing the Larry O’Brien trophy back to Portland after a 40+ year detour.

This brings us to: “To trade or not to trade Dame, that is the question.”

Having been a strong proponent of trading Lillard in the past, I’ve landed in a very unexpected place. No doubt a byproduct of the above-referenced thought exercises, otherwise known as my previously written articles, hence the recap. But be not dismayed; I’ll now lay out why the Trail Blazers should keep Dame until he reaches a ripe old age basketball-wise, the reasons for my about-face.

Before embarking on this thought journey, I was rather insistent the Blazers trade Lillard. While I liked the thought of the greatest Trail Blazer of all-time retiring a Blazer, the sentimentality of it didn’t carry near as much weight as what I believed the clearest path to championship contention was – trading Dame. My reasoning for arriving at this destination was 3-fold.

1. McCollum has another gear in him in Lillard’s absence, which he’s demonstrated in New Orleans for the Pelicans as their lead/point guard.

2. The haul the Trail Blazers would reap had they traded Dame. I was particularly gung-ho about one such rumored trade, which I viewed as a no-brainer at the time – Ben Simmons, Tyrese Maxey, and Matisse Thybulle, plus an untold number of future 1st round draft picks.

While I’m still a believer in Ben Simmons, if you were to anoint him, your PG designate and scheme to his strengths, especially offensively, it remains to be seen if he can overcome his obvious case of the yips. Maxey, though, is already even better than I thought he’d be this early in his career, and Thybulle is now a Blazer.

3. The Trail Blazers likely have to gut the team, present and future, to get Lillard the caliber of player needed to make a deep run into the playoffs. The risks just not outweighing the reward of only making a deeper run and not winning a championship.

But alas, the team was gutted anyway! Neil Olshey “went for it” in his last 1+ year at the helm but ultimately was undone by the team not having its full complement of players but in fits and starts due to injuries. Well, that and Olshey being a prick, per sources, just not mine, at least any that I’m going to out. This story has already been told anyway. What it did do, though, is ushering in the newest chapter in Blazers’ history, the Joe Cronin Era, aka Mr. Nice Guy.

Thus far, said era has been a mixed bag at best, with the team having fully embraced “the tank” the last two seasons. No wonder Lillard is fed up, losing sucks! But despite all of Dame’s very public bluster, it is incumbent on Cronin to do what’s best for the franchise and not just Lillard, like he did around this time last year by drafting Shaedon Sharpe. Joe Cronin’s niceties will surely be put to the test.

Here is the roadmap I’m trusting he’ll adhere to, but not necessarily in this order, particularly steps 1 & 2:

1. Pick Scoot Henderson or Brandon Miller in the NBA Draft on Thursday, June 22nd, with the 3rd overall pick.

2. Trade Anfernee Simons and possibly the 23rd pick for a player of Draymond or Siakam’s ilk.

As another aside, it pains me a great deal to part with Simons as I viewed him and Sharpe as the Trail Blazers’ “Going For It” backcourt of the future, but I now see the value in parting with him after landing the 3rd pick. The caveat, of course, is who the Blazers are getting in exchange for Anfernee.

3. Resign Jerami Grant.

4. Hope and pray for a season of reasonably good health, which should mark the Trail Blazers’ return to the playoffs, and the draft pick they owe to the Bulls finally being conveyed.

5. Trade future 1st round picks, and I mean as many as necessary, to get Dame, Jerami Grant, and hopefully Draymond Green or Pascal Siakam even more help.

This, to me, represents the best path forward, the threading of the needle between present championship contention, with Lillard still leading the charge, and future championship contention, with Shaedon and Scoot or B. Miller leading the way.

If this isn’t enough to placate Dame, I don’t know what would be, but I’m not trading him unless he demands it. And if it comes to that, Cronin’s first two calls should be to the Boston Celtics and the Minnesota Timberwolves. If I’m trading Dame, then for starters, I want either Jaylen Brown or Karl-Anthony Towns.

I’d prefer to do right by Lillard AND the not-too-distant future of the franchise (Sharpe & Henderson or Miller), but I’d leave it to Dame to decide what’s most important to him, chasing championships elsewhere or retiring a Blazer.

He could have it all, though (championship chasing & retiring a Trail Blazer) if Mr. Nice Guy would but follow this roadmap or something in very close proximity to it. Fingers crossed!

Avatar photo
About Jason Poulsen 17 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.