Simons Says Give Penny A Chance And … An Ode To Jack Handy And His Deep Thoughts

With the Portland Trail Blazers 2024-25 season being kicked off with Media Day, here’s what I’ve been thinking about.

There seems to only be one outstanding question about Shaedon Sharpe, and it has precious little to do with how good he’ll be, which is all but a given just two years in.  He’s expected to be really good, as in All-Star upside good, but it wouldn’t surprise me if he ends up being really, really good, as in All-NBA caliber.  The only thing then standing between him and stardom is availability.  Can he stay healthy enough to reach his ginormous potential?

Before his rookie campaign, Scoot Henderson also seemed destined for stardom but fell well short of expectations his first year.  And while I still get Russell Westbrook-esque vibes from Scoot, he does have much to prove this year.  (Love him or hate him, Westbrook is a multi-time All-Star, All-NBA team member, and former MVP, just saying!)

Step 1 in helping Henderson prove himself, as painful as it was to part with Malcolm Brogdon, was clearing the runway at Point Guard.  Much has also been said and written (even here at OSN) about how the way needs to be further removed, with PG also being Anfernee Simons’s best position.  But I don’t count myself among these masses.

Simons and I say, let’s first give the backcourt pairing of Scoot “To My Lou” Henderson and Anfernee “Penny” Simons a chance!

While Anfernee is unquestionably Portland’s best player at the present time, we still don’t know how high his ceiling is.  The Trail Blazers could always go the way of Jermaine O’Neal and trade “Penny” away as the means of finding out.  But I would much rather they take a wait-and-see approach as to whether Simons can become an All-Star.

As a refresher, against the backdrop of the Blazers’ gray sky of a season, Simons was a ray of sunshine:

In his first season sans Dame, his age 24 season, he averaged 22.6 points on 43% shooting, including 3.4 3pm on a 3P% of 38.5%, 5.5 ast, 3.6 reb, and 0.5 stl. Not too shabby!

In Lillard’s age 24 season, his third year in the league, he averaged 21 points on 43.4% shooting, including 2.4 3pm on a 3P% of 34.3%, 6.2 ast, 4.6 reb, and 1.2 stl.  Pretty comparable, right?  But at a fraction of the cost.

Simons [made] $24,107,143 [last]year, while Damian Lillard [made] $45,640,084.  The best part is that Anfernee Simons [was]24, and Dame [was]33.  That’s a savings of $21,532,941 and 9 years for this comparably raw statistical production.

Now, before you go all apples to oranges on me, let’s check in with Lillard to see how he [did last]year – [24.3 pts on 42.4% shooting, including 3.0 3pm on a 3P% of 35.4%, 7 ast, 4.4 reb, & 1 stl].  Not so apples to oranges, is it!?

And virtually no one was as preoccupied with Damian Lillard’s defensive limitations going into his 4th year as people seem to be with “Penny’s” going into next season.  At least with Simons, he really is trying, so there is hope for improvement.

In absence of a veteran mentor (a role Malcolm Brogdon seemed perfectly suited, See The Next Man Up, Exhibit 1B), a strong argument should be made for Anfernee Simons being the perfect catalyst for Scoot Henderson’s development as his running mate.  For Anfernee being Batman to Scoot’s Robin!

Let’s start with the obvious – shooting, shooting, and more shooting.

The more room Henderson has to “Scoot To His Lou,” the more likely he will be to flourish.  Simons will be leading the space, creating a charge as one of the best shooters in the NBA.  If he had played in the minimum games required, he would’ve been among last season’s leaders in 3-point shooting, his 3.4 makes ranking 6th between Klay Thompson and Paul George, and his 38.5% clip ranking 65th (not elite, but still pretty good considering his volume of 8.8 attempts, which would rank 4th).

Now let’s delve a little deeper, rewinding the tape back to Scoot Henderson’s first ‘Professional’ season – year one with the G-League Ignite – when far fewer were questioning if he was going to be a transcendent NBA player.

Another redux:

“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.”

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

Scoot just being able “to play and not think” as Simons’ fearless sidekick is a great recipe for Henderson being able to regain his confidence and swagger, to him being able to play with bad intent, ala Russell Westbrook.

And now for [A] Deep Thoughtbut by Jason Poulsen (Sorry Jack!)

The Portland Trail Blazers Rais[ing]the White Flagg is a record I’ve played before, and Cooper Flagg has since taken it upon himself to do his own raising.  After his performance as a member of the USA Select Team, his profile has never been higher.  Just ask his teammates, who were raving about him.  Or, if you prefer, you could ring up Kevin Garnett and ask the Big Ticket what he thinks of Cooper Flagg.

Call blocked? Not to worry, here is what KG said:

“I could see kids wanting to be like that and play like that… We ain’t have no cold a** white boy like this in a long time!”

Since there obviously is no toppin’ the Big Ticket, nuff said!  But this case is far from closed.

As thrilled as I would be for Portland to win the Cooper Flagg Sweepstakes, it would be a gross miscalculation for the Trail Blazers to embrace the tank from the jump.  While I could get behind them pivoting to tank mode, as they’ve deftly done three seasons running now, this should not be the goal at the onset of this season.

The goal should be to win, plain and simple!

Many a re-toolings, rebuilds have gone off the rails after there has been too much losing.  If you’re not playing to win, if you’re not playing for each other, then what are you playing for!?

Such an environment breeds selfishness and undermines organizational culture.  Losing permeates everything if it goes on too long; it becomes what most characterizes the culture.  And I believe, quite strongly, that the Blazers have reached a tipping point.  And Anfernee Simons seems to concur:

“We don’t want to have another year like this. My sixth year is done now, going into year seven, I want to have the opportunity to win.”

This is the year Joe Cronin gets to decide what type of franchise the Portland Trail Blazers are going to be.  He certainly seems to be leaning heavily to the side of development, which is code for losing, surely in hopes of winning the now-even-longer-odds draft lottery.

Might he surprise us, though?

A mark of a good leader is knowing when to lead and when to get out of your own way. And I really think Simons has the right idea: It’s time to compete, it’s time to win!

And one final Thought, just not as Deep

I was as flummoxed as anyone when the decision was made not to have Scoot Henderson participate in the summer league.  Why wouldn’t Portland want to allow Henderson to dominate and continue building off his strong finish to the season?  Why wouldn’t the Trail Blazers want to give Scoot Henderson and Donovan Clingan a head start on developing their on-court chemistry?  Etc., etc., etc.

There was much hand-wringing over this decision, but while researching this article, I was reminded of Scoot injuring his shoulder in his one and only summer league game before his rookie season.  Clearly, the Blazers decided the risk of injury outweighed any potential benefit.

Having remembered this, I now completely understand the decision and have stopped wringing my own hands over it.  There is no conspiracy, after all.  I had even been mulling over some of my own, but the truth of the matter won out!

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About Jason Poulsen 21 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.

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