As of this season, Portland Trail Blazers General Manager Joe Cronin has held the central seat in the organization for five years. To mark the anniversary, we’re looking back at various aspects of his tenure, examining the ups and downs of Portland’s performances during that span.
Thus far we’ve evaluated Cronin’s trades with a B+ grade, and his extensive drafting history with a B. Let’s dive in to review how he has fared with free agency and managing the salary cap.
Cronin kicked off his major work in free agency back in 2022 by re-signing incumbent free agents Anfernee Simons to a 4-year, $100 million deal, and center Jusuf Nurkic to a 4-year, $70 million contract. Since the Blazers didn’t have cap space, and both players at that time cost more than a mid-level exception, re-signing both represented the best talent they could afford within NBA salary cap rules. Both contracts were overpays, but both were crucial in using for trades that shaped the current roster.
Gary Payton II would be Cronin’s first attempt bringing an outside, unrestricted free agent to Portland via the Mid-Level Exception. Cronin signed Payton to a 3-year, $28 million deal. GP2 was fresh off providing a bench spark plug for the Golden State Warriors’ championship run. His calling card was being a pit bull on defense (something Portland’s guard corps struggled with.) Alas, Payton II would only play 15 games for the Blazers, dealing with extended injuries that raised questions about his desire to be in Portland. This situation may be the strangest in Cronin’s tenure, as Portland traded Payton back to Golden State by that year’s trade deadline. He failed his physical, but the Warriors held on anyway, instigating public jawing and accusing Portland of being shady with medical records. Let’s put this one behind us.
\*The Blazers also signed The Shaq of Troutdale, Drew Eubanks this year. GRADE A+ (heh heh)
In 2023 Cronin matched the Dallas Mavericks’ offer sheet for restricted free agent Matisse Thybulle of 3-years, $33.5 million. Tisse is a great teammate and defensive savant, however, he’s since played in 19 of the past 130 games. He’s now an expiring contract. Unfortunately, I have to give this signing a poor grade because Thybulle’s availability has been a liability.
Roster incumbent Jerami Grant became an unrestricted free agent in 2023, in search of big dollars. Damian Lillard requested a trade almost simultaneously with Cronin re-signing Grant to the tune of 5 years and $160 million! As the Blazers shifted into rebuilding mode, a steady veteran like Grant was a pillar to help in the development of the youth movement. Grant was conceivably Portland’s biggest name unrestricted free agent since Lamarcus Aldridge. It’s possible Cronin had seen how letting good talent walk for nothing in return damaged the asset reserve. The contract to Grant was an overpay, yet it gave Cronin a piece to theoretically move later down the road. Well, it’s a couple years down the road, and Grant’s contract is seen around the league as a difficult one to trade.
To start this season, Grant was moved to the bench and immediately thrived. He looked like the best version of himself as a 6th Man sniper. That development raised a question for fans: Should Grant now be kept long-term with his new role fitting like a glove?
Like most of the roster, Grant has been struggling with injuries for the past month. If Cronin ever wants to move Grant, he’s going to need creativity to thread the needle of the existing 3 years and $103 million left, counting this season. Productive Grant is cool. The money owed and years remaining is not.
Exactly 749 Days after Damian Lillard requested to be traded, he signed a 3-year, $42 million Mid-Level Exception contract with…the Blazers! The guard had been waived by the Milwaukee Bucks after rupturing his Achilles Tendon in the spring. (At that point he still had 2 years and $112 million remaining on his contract. I wanted to include that extension signing as something to critique Cronin on, however, the fact the Bucks are eating the entire thing by stretching it to $22.5M annually over the next 5 years, is what the kids would call “diabolical work.”) Lillard might have destroyed the OKC franchise back in the day, but Cronin the Barbarian earned that nickname by teaching the Bucks franchise the Riddle of Steel.
Lillard’s homecoming was (and is) a happy story. After leaving the organization with apparent bad blood, Dame found enough happiness to come home and rehab. The team has drastically changed since he left, both in personnel and playing style. How he fits in, and to what level he physically returns, are major questions. However, Lillard remains one of the scariest players in the league with the ball in his hands in the clutch. No matter how things eventually go for Dame, him coming back to Portland to finish his career on a highly affordable deal with a massive chip on his shoulder is great cinema.
It should be noted that Cronin and his management team have really done a great job working around the fringes when it comes to recent two-way contracts. Currently, we’re seeing some fantastic growth and performances from Caleb Love and Sidy Cissoko. Both players are looking like regular-contract candidates. Duop Reath also started as a two-way player before earning a veteran’s minimum deal with the Blazers. These three help cover up some of Portland’s free-agency droughts.
Still, the area has not been a strong suit. However, when you enter a rebuild as a small market that historically struggles in this department, free agency takes a backseat as a player acquisition vehicle.
**OVERALL FREE AGENCY GRADE: C-**
When Cronin took over for former President of Basketball Operations Neil Olshey, the Blazers had paid luxury tax penalties in two out of the previous three seasons. They were on track for three out of four. That would have triggered the Repeater Tax penalty for the 2021-2022 season, a sizable price tag for a declining roster.
With Lillard already shut down for the season with an abdominal injury requiring surgery, Cronin’s first major move as General Manager was to shed salary and get under the tax line. On February 4th, 2022, Cronin traded Robert Covington and Norman Powell to the Los Angeles Clippers for Eric Bledsoe, Keon Johnson, Justise Winslow and a 2025 second-round draft pick.
That trade was criticized because of the gap in talent going out versus coming back in. That’s fair. Bledsoe never suited up for Portland. Winslow was chronically injured and could only cobble together a small run of games. Keon Johnson represented a shot in the dark on a young, athletic talent. It didn’t pan out. Could Cronin have found a better return elsewhere? Perhaps.
However, that’s not the lens through which to view this trade. This was a salary dump to get under the tax, then clear $18 million off the books with Bledsoe’s expiring deal. It might have been messy, but so was the imbalanced roster. Teams were holding more leverage in trade negotiations against the Blazers, who were actively looking to duck under the tax. [Cronin addressed that when discussing the Clippers trade in his 2022 post trade deadline presser.](https://www.kgw.com/article/news/local/trade-deadline-joe-cronin-blazers-press-conference/283-9cb7aeca-b02a-44c7-8441-ff07afc4d2fc)
_“The deal was important for us because it got us out of the luxury tax this year, which completely reset our repeater clock, meaning we won’t go back in, even if we’re in the tax in future seasons, until at least 2025._ **_And the deal also gave us a bunch of leverage in the next deals that we needed to make, where teams would no longer hold getting us out of the luxury tax as part of the negotiation._** _So that was a good deal for us.”_
The Clippers move allowed Portland to get the deal they were seeking from New Orleans. They essentially turned CJ McCollum and the first-round pick he was traded for into Josh Hart and Jerami Grant. These two trades represented Cronin’s only attempts to retool around Damian Lillard with impactful veterans, still keeping the team below the tax threshold.
When Lillard was traded in 2023, the Blazers were still butted up close to the tax line. Instead of actively trading high-priced vets like Deandre Ayton and Grant to create more flexibility to take on salary dumps like a lot of rebuilding teams do; the Blazers decided to use the talent as a helpful transition bridge for the ensuing youth movement. When Ayton was waived this past summer, the Blazers eventually saved $10 million on what they owed him.
Ayton’s former salary can be considered earmarked, covering most of the extension costs for Shaedon Sharpe and Toumani Camara that kick in next season. Sharpe’s salary jumps from $8.4 million this season to just over $20 million next, while Camara goes from $2.2 million this year to $18 million next. Considering the Kings just signed Sharpe’s draft contemporary, Keegan Murray, to a 5-year, $140 million extension, the numbers for Camara and Sharpe look like great contract extensions for two crucial players in Portland’s rebuild.
Last summer’s trade that sent Anfernee Simons and his expiring $27 million deal to Boston for Jrue Holiday was a financial head-scratcher. The 36-year-old Holiday has three years and $105 million remaining on his contract. That’s a big pill to swallow for a player whose body is showing signs of decline. Holiday still has game, and his leadership is legendary, but the jury is out on how this trade ultimately affects the Blazers. With Deni Avdija’s next contract on the horizon, as well as a decision on Scoot Henderson’s future extension, the Blazers will likely be turning over a franchise ready to go into the tax to new owner Tom Dundon. That is, unless one or both of Grant and Holiday are traded to bring them back below. At some point, if you want to contend, you gotta spend!
Just about all of Cronin’s tenure has been about retooling and rebuilding. He’s kept his ownership from paying the tax under his watch while still adding talent. The extensions for Sharpe and Camara were solid deals and are quite tradable. If Grant and Holiday are still here a year from now there may be trouble. There’s work to do yet, but the project isn’t finished either.
**SALARY CAP MANAGEMENT GRADE: B**
We’ll have one final article to come to finish this series, as we discuss the culture Joe Cronin has created over his 5 years. Until then, what are your thoughts on Cronin’s work in free agency and managing the cap?
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