The Portland Trail Blazers have long been a team that has had success in the NBA. With stars like Damian Lillard and CJ McCollum leading the way, the Blazers had been a perennial playoff team. They still might make the play-in tournament this season where anything can happen.
But the Blazers have struggled to make a deep playoff run in recent years, and they are in danger of losing some key players this summer.
This offseason, the Blazers are faced with some important decisions. Several of their key players are set to become free agents, and the team must decide whether to re-sign them or let them go.
With the offseason rapidly approaching, it’s time to take a look at some of the most critical free agents that the Blazers need to re-sign to blaze a trail to success in the NBA.
Priority No.1: Re-sign Jerami Grant
When the Blazers sent a 2025 first-round pick (via Milwaukee), the 36th pick of the 2022 NBA Draft, a 2025 second-round pick, and a 2026-second round pick to Detroit for Jerami Grant, they had every intention of keeping him in Rip City for the foreseeable future.
Grant is a key piece to building a team around Damian Lillard that can compete for an NBA title.
In Grant’s first season with the Blazers, he’s averaging 20.7 points per game while shooting a career-best 48 percent from the field and 39.9 percent from three. He’s averaging 35.6 minutes per game and playing strong defense.
Earlier in the season, he was trending toward his first all-star appearance, and at 28 years old, he’s in his prime.
The Blazers already offered Grant a four-year, $112 million extension, the max contract possible at the time, but Grant said he was focused on the season and would wait to sign an extension.
Grant: “I’m kind of focused on the season at hand right now. Probably will wait until after the season and talk to (GM) Joe (Cronin). Everything is good. I like it here. Really enjoying it. So, yeah … we will discuss it when it’s time.” (2/3)
— Jason Quick (@jwquick) January 31, 2023
After July 1, the Blazers can offer Grant a max contract of five years and $233 million. Other teams will only be able to offer him a max of four years and $174 million.
The Blazers need to offer Grant the max contract possible and keep him in Portland as an essential piece next to Lillard and whichever superstar they can potentially acquire this offseason.
Priority No. 2: Cam Reddish, Matisse Thybulle, and Kevin Knox
The Blazers are always on the lookout for talented players who can help them compete at the highest level. They did what they could at the trade deadline and acquired some promising young players in Cam Reddish, Matisse Thybulle, and Kevin Knox.
This offseason, they will need to decide whether or not to extend qualifying offers to Reddish or Thybulle and pickup Knox’s team option.
Reddish has started every game since being acquired, and it has been easy to see the potential in his game – and he’s only 23 years old.
He’s shooting 44.8 percent from the field and 35.1 percent from three while adding much-needed length to the Blazers’ lineup. At this point, Portland should extend Reddish the $8,109,966 qualifying offer. This would give the Blazers more depth to work with moving into next season without tying up a lot of cap space.
Keeping Reddish also makes it easier to acquire a star by having multiple options for matching contracts in a trade scenario.
After being acquired, Thybulle said per Sean Highkin of Rose Garden Report newsletter and podcast, Portland is “…home to me. I’ve done countless weekend trips with my friends from Seattle to Portland. I’ve done all the hikes and seen all the waterfalls out here.”
He’s certainly playing like he wants to be a Trail Blazer. The two-time All-Defensive Second-Team guard is shooting 51.6 percent from the field and a career-high 54.5 percent from three. Even if his scoring numbers regress, his elite defense and love for Portland make him an invaluable rotation piece alongside the elite scoring guard duo of Lillard and Anfernee Simons.
Ma-Threese is a steal if he accepts his $6,275,861 qualifying offer.
Knox has only played 5 minutes per game in his four games as a Blazer. Although he’s only 23 years old, he’s in his fifth NBA season and has not shown enough to crack a starting rotation since his rookie year.
It’s clear that the Blazers’ coaching staff does not see him as an essential piece and would likely be better off saving the $3,000,000 in cap space this offseason.
Priority No. 3: Justise Winslow, Drew Eubanks, and Ryan Arcidiacono
In addition to the aforementioned players, the Blazers will need to decide whether or not to offer pending free agents Justise Winslow, Drew Eubanks, and Ryan Arcidiacono contract extensions.
Winslow is a talented player with a diverse skillset that has battled injuries his entire career. He’s been out since Dec. 21 with no signs of returning.
In an NBA.com interview, Winslow said, “I’ve found a home… I don’t want to go anywhere.” If Winslow is willing to return on a reasonable deal of around $3-4 million per year, he could be a nice rotational piece to back up Grant.
Keeping Reddish, Thybulle, and Winslow in town, alongside Nassir Little, would give the Blazers a lot of trade filler options when trying to acquire a star.
Eubanks has been an absolute steal at just a $1,968,175 guaranteed contract this season. He’s done an admirable job filling in for Jusuf Nurkic, and the Blazers should re-sign him as a backup center.
Eubanks brings energy to the lineup and is strong in small-ball lineups as a player who can be disruptive. He’s also averaging 1.2 blocks per game. The Blazers should resign the Trout of Shaq-dale and let him continue putting the opposing team into the vault.
Arcidiacono may not be the flashiest player on the court, but his hard work, energy, basketball IQ, and locker room presence have earned the respect of his coaches and teammates everywhere he’s played.
With Simons out, coach Chauncey Billups has given Arcidiacono some extended playing time when Lillard is resting. However, the fact that Trendon Watford appears to be handling the on-ball duties behind Lillard as often as Arcidiacono shows that he’s not likely a long-term piece for the Blazers.
Although he’s a nice piece to have, the Blazers should let him walk this offseason, unless he wants to come back at the minimum.