The Portland Trail Blazers have a massive decision to make in the coming months. Superstar Damian Lillard has requested a trade, and the franchise must maximize their return if they want to quickly jump back into contention. Dame is still one of the best players in the league, but can Joe Cronin and the front office get enough back in return to make the deal worthwhile?
Cronin has been the team’s general manager and lead decision-maker since Dec. of 2021, but he has been with the franchise since 2006. He was named Director of Player Personnel in 2014 and promoted to assistant general manager in 2021 just before Neil Olshey was fired. Cronin became interim GM after Olshey’s exit and the team dropped the interim tag in May of 2022.
Cronin has been involved in a lot of key decisions since joining the Trail Blazers. Some of the team’s worst have come after he took over the top role. Portland has made plenty of regrettable moves since Cronin was promoted in 2014, but which are the worst?
Worst Portland Trail Blazers moves of the Joe Cronin era
10. Bob Cov trade
In 2020, the Blazers traded Trevor Ariza and two first-round picks to the Houston Rockets to get Robert Covington. Ariza was past his prime and traded three times over five days before landing with the Thunder. OKC sent him to the Heat four months later in what turned out to be his second to last season.
Covington was a valued commodity, but was he worth two first-round picks? He played a key role for the Blazers in 2021 but was shipped out at the 2022 trade deadline in a regrettable deal for Portland that features later in this countdown.
The Portland Trail Blazers paid a massive price to get Robert Covington and traded him 16 months later for significantly less. Covington’s defense slipped a bit in Rip City as he began to decline, and the franchise likely wishes they never acquired him.
9. Re-signed Meyers Leonard in 2016
The Blazers drafted Leonard 11th overall in 2012, and he showed improvement in his first four years. The seven-footer never broke into the starting lineup, but he averaged 8.4 points and 5.1 rebounds in 21.9 minutes per game just before he became a free agent.
Leonard was also helped by the massive cap spike in 2016. The $24.1 million increase left every team with money to spend, and the 24-year-old inked a four-year $41 million contract to stay in Portland.
Leonard’s playing time decreased immediately. He never worked his way into a starting role as the seven-footer averaged 5.2 points, 3.2 rebounds, and 1.0 assist in 14.0 minutes per game over the next three seasons combined.
The Trail Blazers traded him during the 2019 offseason in a four-team deal that sent Hassan Whiteside to Rip City. Whiteside’s stay lasted just one season but was a significant upgrade over Leonard.
Meyers Leonard was the 114th highest-paid player in the NBA in the 2016-2017 season as he made nearly double the mid-level exception. It was a disastrous deal that the Blazers luckily got out of a year early. Leonard never reached his ceiling, which meant the Portland Trail Blazers were stuck overpaying him for years.
8. Trading Batum to Hornets
The Trail Blazers were forced to pivot in the 2015 offseason after four-time All-Star LaMarcus Aldridge departed in free agency. Portland had made two straight playoff appearances and was hungry to stay in contention. That meant shaking things up and trying to get younger to replace Aldridge’s star power.
Just before free agency opened, the Blazers traded Nicolas Batum to the Charlotte Hornets for Gerald Henderson and Noah Vonleh. Henderson had been the Hornets’ starter for the last four years, but he was a shooting, playmaking, and defensive downgrade from Batum. The deal hinged on Vonleh’s development.
The 6’10 forward had a slow first season in Charlotte after being the ninth overall pick in 2014. He was a project that never reached his potential and was dumped after two and a half seasons in Portland.
This trade went from bad to worse as Batum took his game to a new level in Charlotte, and Henderson declined in Portland. Over the next two years, Batum averaged 15.0 points, 6.2 rebounds, 5.8 assists, and 1.0 steal in 34.5 minutes per game. Henderson lasted just one season with the Blazers where his minutes and production declined across the board.
This trade became a disaster and is one Neil Olshey, Joe Cronin, and the Portland Trail Blazers wish they could have back.
7. Allen Crabbe contract
Crabbe was the 31st overall pick in the 2013 draft and had a breakout third season just before he entered restricted free agency. The 6’5 wing averaged 10.3 points, 2.7 rebounds, and 1.2 assists in 26.0 minutes per game, and the Blazers wanted to continue developing the 24-year-old.
The 2016 cap spike left every team in the league with money to spend, and the Brooklyn Nets were hoping to add some young talent to their roster. They gave Crabbe a four-year $75 million offer sheet, which Portland matched. It paid Crabbe $18.8 million per season and made him the 31st highest-paid player in the NBA during the 2016-17 campaign.
Crabbe never fully broke out and the contract quickly became a negative value. The Blazers traded him to the Nets in 2017 for Andrew Nicholson, who they used the waive and stretch provision on. Portland still has a cap hit on their books because of Nicholson, but it was better than handing out that massive money Crabbe.
Allen Crabbe was out of the league by 2020. His defense and playmaking never improved, so he was just a shooter. Crabbe connected on 40 percent of his threes in just one season. His jumper was not good enough to make up for the rest of his game.
6. Evan Turner contract
If two nightmare moves in the 2016 offseason were not enough, the Blazers made a third when they gave Turner a four-year $70 million contract in free agency. The deal made him the 47th highest-paid player in 2016-17. Turner earned more than Stephen Curry, Draymond Green, Gordon Hayward, and Kyle Lowry, who were all All-Stars in 2017.
Turner averaged 9.0 points, 3.8 rebounds, and 3.0 assists in 25.5 minutes per game. It was a significant step backward from the previous season and turned out to be his best year in Portland. The Blazers did reach the conference finals in 2019 with Turner playing a 15-minute per-game role off the bench, but he was not a clear fit in a league that valued floor space more than ever.
Portland traded Turner to the Hawks for Kent Bazemore in 2019, and he lasted just one more year in the league before retiring in 2020. Bazemore was traded to the Kings in Jan. of 2020, but the Trail Blazers were happy to clear Turner’s contract off their books.
Joe Cronin was the Director of Player Personnel for all of the moves so far. He had a hand in them but was not the Portland Trail Blazers lead executive. Since taking over in 2021, he has made his fair share of regrettable moves and the top five will detail the worst ones.
5. Signing Gary Payton II
The Warriors wanted to bring back Gary Payton II after their 2022 title run, but the team had to watch their spending. There was no second luxury tax apron at that point, but Golden State knew a massive tax bill was coming and every additional dollar meant spending significantly more than that.
The Blazers swooped in and signed Payton II to a three-year $26.1 million contract that the Dubs just could not match. Portland was excited about his defense and developing jump shot, but they overlooked his flaws.
GPII was approaching his 30th birthday and had played more than 30 games in an NBA season just once. Even in his breakout year with the Warriors, he averaged 17.6 minutes per game. The Trail Blazers were expecting him to play a key role, but Payton II was getting just 17.0 minutes a night before being traded back to Golden State just eight months after leaving.
The Portland Trail Blazers got five second-round draft picks and Kevin Knox in the four-team trade, which was a massive haul for a bench player that is making $8.7 million per year. Credit to Cronin for finding the right trade because the signing could have come back to bite the Blazers.
4. Josh Hart trade
This trade may not look bad on paper. The Blazers got three players and a first-round pick in exchange for Hart one year after they acquired him in the CJ McCollum trade. This eventually became a four-team deal with the Matisse Thybulle trade lumped in. Portland gave up two second-round picks to get Thybulle, and none of the players they acquired from the Knicks remain on the team.
The first-round pick was used on Kris Murray, and it is too soon to say how that will work out.
Hart took his game to another level with the Knicks. He averaged 10.2 points, 7.0 rebounds, 3.6 assists, and 1.4 steals in 30.0 minutes per game and immediately helped them reach the second round of the playoffs.
Hart just got a four-year $81 million contract extension. That is massive money and more than Portland wanted to spend. Still, it feels like they should have got more than the 23rd overall pick for a player that is now making more than $20 million per year.
This was another key factor in the Damian Lillard trade request. The seven-time All-Star formed a tight bond with Hart during his year in Portland and the trade further proved the Blazers are not ready to contend.
3. Overpaying Jerami Grant
The Blazers were desperate when free agency opened in 2023. They gave up one first-round draft pick and two second-rounders to acquire him just one year earlier. Portland did not want that to be for just one season, especially a year where they won 33 games and missed the playoffs.
The Trail Blazers also knew they had to do whatever they could to keep Damian Lillard happy. He wanted roster improvements, so they could not lose Grant for zero return if they hoped to keep one of the franchise’s GOATs.
Those factors gave Grant all the leverage and the 6’8 forward cashed in with a five-year $160 million contract. He will be tied for the 36th-highest-paid player next season, despite never being an All-Star. Grant is set to make more than Devin Booker, Jamal Murray, DeMar DeRozan, Jaylen Brown, and Jalen Brunson in 2024.
To make matters worse, Lillard requested a trade before Grant officially signed the deal. The Portland Trail Blazers could not go back on their word. Grant will be the team’s highest-paid player if Lillard is dealt, and Portland will have to figure out how to make him part of their rebuild.
This deal will likely look worse as Jerami Grant exits his prime. He turns 30 in March and will be 33 when deciding on his player option in 2027-28. It is not a fantastic place for the franchise to be.
2. Powell and Covington trade
Norman Powell signed a five-year $90 million extension with the Trail Blazers in the 2021 offseason before being traded to the Clippers at the 2022 deadline. It was not a great look for general manager Joe Cronin and the haul he got back made it even worse.
Portland gave up two first-round picks to get Covington in 2020 and just over one year later he was traded with a wing that averaged 18.0 points, 3.3 rebounds, 2.0 assists, and 1.1 steals during his 67 games with the Trail Blazers for virtually a second-round pick. Powell is the Clippers’ sixth man and a key contributor that would be traded for more than a second-round pick right now.
Eric Bledsoe never played for Portland. Keon Johnson averaged 10 minutes per game in his second season, but it is too early to write him off completely. Justise Winslow struggled to stay healthy and played just 40 games in Portland over the next year plus.
Without Johnson becoming a starter and key contributor, this looks like an awful trade for Portland where they shipped out two capable rotation pieces for one second-round pick. Yes, Covington fell out of the Clippers’ rotation last season, but the 6’7 forward can still space the floor and make an impact in the right role.
Consider this trade a disaster, but one the Portland Trail Blazers have already paid for. The top move on this list still has the rent due.
1. Re-signing Jusuf Nurkic
The Trail Blazers have tried to keep a competitive team around Damian Lillard in recent years, and it immediately resulted in some regrettable moves. Portland acquired Nurkic and a first-round pick in 2017 for Mason Plumlee and signed him to a four-year $48 million extension in 2018. It allowed him to hit the open market again in 2022, and Joe Cronin and the front office locked him up to an even bigger deal without seeing the red flags.
In the three years before signing his new contract, Nurkic played a total of 101 games, or just 33.6 per season. Injuries set him back every year, and the Blazers were coming off a bad season. None of that mattered. They still inked him to a four-year deal worth $70 million.
After a fourth straight injury-plagued year, no team in the league wants to trade for Jusuf Nurkic. The soon-to-be 29-year-old has $54.4 million remaining on his contract and does not become a free agent until 2026. How many games can the Blazers expect at this point? It is a bad situation and arguably the worst move of Joe Cronin’s tenure as the team’s lead decision-maker.
Should Portland Trail Blazers fans have faith in Cronin to make the Damian Lillard trade? It is a fair question to ask. Most of these moves are regrettable at best, and the franchise needs to maximize its return if it wants to bounce back quickly. Will Joe Cronin make the right deal? Stay tuned to find out.
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