The Portland Trailblazers are 33-46 and 13th in the Western Conference standings, staring another trip to the lottery in the face. Another wasted season during the prime of Damian Lillard, and the Trailblazers have to be feeling a sense of urgency to not waste his entire tenure. In order to capitalize on Lillard's greatness, the Trailblazers need to take advantage of this off-season, starting with the 2023 NBA free agency. Before they go after opposing teams' free agents, they need to secure their own.

Portland has a multitude of players that they will either need to re-sign or let go this summer. A total of eight Trailblazers will hit the market, and Portland will have to make some difficult decisions in letting a few of them go. General Manager Joe Cronin has three players that are absolutely imperative to re-sign. If he keeps these three players, and adds another star to go alongside Lillard, Cronin could build a championship caliber roster. So, who are those three players?

The three best players Portland must re-sign in 2023 NBA free agency.

*Stats via ESPN

Jerami Grant

The Trailblazers traded for forward Jerami Grant during the 2022 season, and he has fit in nicely in Portland. He was having a solid first full Trailblazers campaign in 2023, averaging 20.5 points and 4.5 rebounds per game, going along with a career-high 40.1% from the three-point line. He was gearing up for a playoff push before sustaining an injured quad that has kept him sidelined since the middle of March. He looks unlikely to play again in another lost season in Rip City.

Despite a less than ideal finish, Grant showed that he could be a serious part of the Trailblazers future. With Lillard and Anfernee Simons making up the backcourt, Grant is a perfect fit alongside them at a forward position. His size creates space for the Blazers guards on the perimeter, and his elite three-point shooting also allows them to drive, or drive-and-kick. Entering his tenth season and at 29 years old, Grant is firmly in the prime of his career. If the Blazers can keep him, Cronin will only have to add a center in order to round out the starting lineup.

Grant will be eligible to sign a five-year deal worth $233 million when NBA free agency starts on June 30th. This might not be what he ultimately signs, but he is sure to obtain some lucrative offers across the NBA. He will be an unrestricted free agent, so Cronin and the Trailblazers brass should prepare to invest quite a bit in Grant. With how well he fits on this roster and the improved chances of helping a Damian Lillard led squad to the NBA Finals, Cronin should give Grant whatever he wants.

Cam Reddish

Cam Reddish was drafted 10th overall in 2019 to the Atlanta Hawks, a highly touted prospect out of Duke. He showed flashes of elite production in three seasons as a Hawk, but ultimately lost the faith of the organization. He was traded to the New York Knicks during his third season, and his career stalled. In 1.5 seasons in New York, Reddish rarely found the floor, as he saw his minutes cut drastically. It wasn't until the trade deadline this year that he reclaimed some form from his days in Atlanta.

The Portland Trailblazers acquired Reddish as part of a deal that saw Josh Hart move to New York. Since his arrival, Reddish has seen his minutes jump up to almost 28 a game, and his scoring is back in the double digits. He has had multiple 20 point outputs since his acquisition and has fit seamlessly in Chauncey Billups' system. The intercontinental move might have just reinvigorated a career that got off to a slow start for Reddish.

Ultimately, Cronin needs to re-sign Reddish for one primary reason; He is 23 years old. Reddish still has the raw talent and athleticism that saw him become a top 10 draft pick, so much so that he is still far from an unfinished product. There was a time, when he was playing alongside RJ Barrett and Zion Williamson, that he was considered to be the best NBA prospect of the three at Duke. Cronin will be able to get the restricted free agent for a relatively cheap price tag given the start to his career, and again, he is only 23 years old. He can be a valuable piece off the bench as he continues to develop, but could easily blossom into a dynamic scorer once he reaches his prime. Once NBA free agency hits, the Trailblazers need to bring back Cam Reddish.

Matisse Thybulle

Matisse Thybulle has had a very similar trajectory to his career as teammate Reddish. He entered the NBA in the same year as Reddish, drafted by the Boston Celtics ten picks after his Trailblazers' teammate in 2019, before being traded to the Philadelphia 76ers the day after. Where he differed from Reddish was his production, as his prowess on the defensive side of the floor quickly made him a huge part of the 76ers and led him to NBA All-Defensive Second Team honors in 2021 and 2022. However, he mimicked Reddish once more this season, as his minutes were cut in half. He eventually found himself on the trade block. At the deadline, the 76ers pulled the trigger and sent him to Portland.

Thybulle has now played 22 games as a Trailblazer, starting all 22. In his time in Portland, he is averaging a career-high 38.8% shooting from the three-point line, a career-high in rebounds, and is back to his averages on the defensive side of the floor during his All-NBA seasons. He has returned to the Swiss-army knife type player he displayed at his best in Philadelphia, and is a perfect fit for a Trailblazers team that struggles defensively. He is also an ideal spell for the aforementioned Grant and Reddish, as he has shown the ability to play whatever role the team needs.

Thybulle is a few years older than Reddish at 26, but is still young in his career. Like Reddish, his price will be cheap and he is also a restricted free agent, so Cronin will have the upper hand in negotiations. He would be smart to keep the valuable role player off the bench that has already shown elite defensive production in the NBA. For what the Trailblazers can get him for, they would be misguided to not hold onto Matisse Thybulle.