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Sharpe v. Simons: Who’s More Likely to Stay with the Blazers Long-Term?

With Portland intending to make a big move this summer, which young shooting guard are they likely to prioritize?

Phoenix Suns v Portland Trail Blazers Photo by Sam Forencich/NBAE via Getty Images

Led by All-Star Damian Lillard, the Portland Trail Blazers are trying to forge their way into the NBA Playoffs. It’s what we’ve heard from General Manager Joe Cronin on multiple occasions and I’ve got little reason to doubt him.

At his recent post-deadline press conference, Portland’s lead executive spoke of being “anxious” to build a contending team, giving him ample time to win it all.

“We’re borderline anxious to push all of our chips in. We cannot wait for that moment to happen, it just hasn’t come up yet. It’s my job to be the voice of reason, to be very diligent to not make a big mistake, to not get the wrong guy, to not overpay, to not give up on somebody that could eventually become a really good player. I’ve got to be really smart about this because it’s trying to thread a really thin needle here. We don’t have room for error, we need to get this right. We wanna maximize Damian’s time.

“I know it’s hard when I come out, like, ‘Oh, well, we’re looking forward to this summer,’ or ‘have faith we can get something done.’ It feels a little empty like it’s false hope or unrealistic promises, but hopefully our track record has shown that we’re willing to be really aggressive.”

“Certain things come into play whether it’s, we got a first and potential now five seconds. Those are good currency in the marketplace and definitely help enhance a package.”

“We’re definitely in position with a better asset pool than we started with and for me that’s really important.”

Social media is rife with Blazers watchers who are unwilling to believe Cronin until he’s able to pull off said deal. And that’s fair given a decade of stalling and over-selling under former President of Basketball Operations Neil Olshey.

We need to remember that this is indeed a new era with a new team building philosophy. It’s a departure from the minor changes made to an already-bloated payroll and a softening on the stubbornness to not include certain players in trades.

We’ve already seen it. In just six months, Cronin boldly and, for some, unpopularly cut salary, cleaned the books and secured Jerami Grant — a mere fantasy under the previous regime.

Now the hard work starts, with Lillard’s prime years ticking away. So what are Cronin’s options? The draft takes too long to deliver NBA-ready players and the team doesn’t have the cap space to entice free agents. Trade is the only way forward and to do any deal of consequence, the Blazers must regain control of their future first round picks.

The New York Knicks first-round pick (or the five second-rounders) yielded at this year’s NBA Trade Deadline will hopefully be enough for the Chicago Bulls to relinquish their hold on the Blazers’ future draft capital, owed to them courtesy of one of Olshey’s last big trades, for Larry Nance, Jr. two years ago.

Great, but in order to pull off the ideal deal, the Blazers are going to have to give up actual basketball players. Eight first rounders (including swaps) isn’t going to be enough to make salaries match. Teams are going to want good young players and/or rookie-scale prospects with ridiculous upside to go along with the bevy of picks Portland might offer.

Scanning players contracted to the Blazers next season, two names pop off the sheet. Anfernee Simons is a good young player and Shaedon Sharpe is the very definition of a rookie-scale prospect with ridiculous upside.

When discussing targets, the Blazers will have to match salary, which becomes complicated with the target likely earning close to max-type money.

Outside Jusuf Nurkic’s relatively unattractive three years and $54 million (at roughly $17.5 million a year), the Blazers aren’t flush with mid-tier deals. In fact, there’s only one, Simons.

The rest of the current 2023-24 roster, not named Lillard, is made up of Shaedon Sharpe ($6.3 million), Nassir Little ($6.2 million), Kevin Knox II ($3 million), Keon Johnson ($2.8 million) Trendon Watford ($1.8 million) and Jabari Walker ($1.7 million).

The other alternative is to wait until January so that the assumed re-signed Jerami Grant, Matisse Thybulle, and Cam Reddish can be included to make the salary work.

I’m not sure anyone inside or outside the franchise has the patience, so a mid-season deal is unlikely an option.

Anfernee Simons

Age: 23 (24 in June)
Experience: Five years at end of season
Contract remaining: Three Years, $77.6 million
Season numbers: 61 games, 21 points, 38% from 3pt, 2.6 rebounds, 4.1 assists, 0.7 steals

Simons is the guy Cronin cleared a runway for just over 12 months ago after he engineered the departures of CJ McCollum and Norman Powell. But as we know, nothing is forever in the modern NBA. Team building requires the changing of plans on a regular basis.

Let me start by saying, I don’t want Simons to be moved. But if a big deal eventuates, his contract, youth and ability seem almost too convenient to exclude. This season, Simons has had to adjust to starting alongside Damian Lillard. He’s suffered a slight dip in efficiency from three, but improved his field goal and free throw shooting.

The 23-year-old is also improving as a facilitator, competently taking ball handling responsibilities from Lillard when the veteran point guards sits.

Chauncey Billups’s third-most-used lineup this season features Simons, Josh Hart, Justise Winslow, Jerami Grant and Jusuf Nurkic. A combination that has delivered a total +19, averaging 9.6 minutes, 22 points, 8.7 boards and 5.6 assists a game — the team's second-best combination of Blazers playing in more than eight outings.

Simons’ departure was felt recently during the six games he took to overcome an ankle injury, with the Blazers’ second unit relying on Trendon Watford and Cam Reddish to initiate the offense. It wasn’t great and the offense was seriously stunted.

While Simons’ defensive shortcomings have been widely discussed, he’s far from a pushover on that end of the floor. He has the foot speed and lateral movement that, when finally mastered, should enable the 23-year-old to be serviceable on that end of the floor.

Shaedon Sharpe

Age: 19 (20 in May)
Experience: One year at end of season
Contract remaining: Three years, $21.3 million (including team options on year 3 and 4)
Season numbers: 69 games, 7.9 points, 35% from 3pt, 2.5 rebounds, 0.7 assists, 0.4 steals

Credit to Jacked Ramsays' Brandon Sprague for coining the “Baby Kobe” nickname. It definitely set an expectation before the season started.

While those expectations are still realistic, the chances of a teenager who didn’t play college basketball becoming an instant star were never high.

Sharpe has skill, athleticism, and is growing his basketball IQ. Becoming the star-like player that Sprague’s moniker suggests is still a tall order, but it appears defense is hindering Sharpe from playing the big minutes he needs to prove his worth.

I’m not concerned. Blown defensive assignments should be expected at 19. If and when he does it put it together, Sharpe’s defensive potential blows Simons’ out of the water.

Two big issues for me. The first is obviously whether he’s able to put it all together. Second, if he does get there, how long does the young Canadian take to figure it out? If Simons is moved in the offseason, Sharpe is nowhere near ready to start.

The latter concern was allayed ever-so-slightly when the Blazers secured Thybulle at the deadline. If Simons is moved, Thybulle can slide in next to Lillard in the backcourt thanks to his elite defense and recent improvement in three point shooting until Sharpe is ready.

The other real issue to consider is that Sharpe will only be earning a smidge over $6 million next season — which won’t really help the Blazers match salary. He’d need to be combined with other contracts in return for a player who’s most likely on his second, third or fourth contract, earning north of $25 million.

But I want to make this abundantly clear though. Sharpe will never be a throw-in for a deal. He’s a centerpiece, and rightly so. That’s amazing to consider, given he’s only played 69 games.

Could both be moved?

Nothing can be known for certain. If a Joel Embiid-type deal is on the table and Philadelphia 76ers President of Basketball Operations Daryl Morey demands both Simons and Sharpe, you do that deal.

I’m sure Cronin will do all he can to keep at least one of them, but if it means the difference between 33-year-old Damian Lillard contending or not, it gets done.

In no way do I get the sense that Cronin views Simons and Sharpe the same way Olshey viewed CJ McCollum. If a deal makes sense for Lillard and his title chances, it gets done.


It’s unlikely the Blazers wait until the 2024 trade deadline just so that they can include contracts signed this summer.

My gut tells me that unless the Blazers can somehow offer up picks, swaps, and filler for a player of consequence, Simons will not be in a Portland uniform next season.

His combined money and potential would no doubt be attractive to the remaining 29 front offices while helping satisfy salary-matching requirements.

Alternatively, a deal involving Sharpe only takes place to enhance a package that already includes Simons...or another deal that brings in an extra difference-maker next to Lillard.

Having said all that, I cannot wait to see what happens through June and July. If and when Cronin regains control of the Blazers’ draft assets we should see attempts at deals to help Lillard compete into the following June.