The Portland Trail Blazers is still considered a small market team, which somewhat makes them not so enticing for big-time free agents.

Still, this hasn’t stopped them from handling out huge bucks to sign or retain some top-notch players from free agency.

But like every team in the league, not every lucrative investment turned out the way they hoped for. They found gold with the likes of Brian Grant and Rod Strickland, but somehow struck out with these five signees.

Let’s rank the Blazers’ worst free agency decisions of all time.

5. Hedo Turkoglu (2009)

This is a peculiar choice considering that the Turkish legend never even logged in a single second in a Blazers jersey.

However, Portland really believed they had the 6-foot-10 stretch forward at their disposal after Turkoglu reportedly gave them a verbal agreement in the summer of 2009. Fresh from the Magic’s defeat in the Finals that year, Hedo initially chose the Blazers as his team of choice and even had a deal in place.

But after a sudden change of heart, he opted to sign with the Raptors for a 5-year, $53 million deal. This, of course, stunned the Blazers who didn’t have a contingency plan in place. Exact figures of Turkoglu’s deal with the Blazers remain undisclosed, but the former Most Improved Player winner reportedly would have made $3 million more annually with Toronto.

The Blazers, of course, wasn’t the one at fault on this one. Still, there’s no denying that Turkoglu would have fitted in nicely with Brandon Roy and LaMarcus Aldridge back then.

4. Pau Gasol

1-year, $2.6 million deal (2019)

Speaking of international stars who didn’t even play for the Blazers, Gasol also fits the bill. The two-time NBA champion was brought in for his winning pedigree and veteran guidance for a short-term deal.

With the Blazers’ frontline already thin due to injuries, the 39-year-old Spaniard added to their woes. Gasol only played three games for the Bucks the season prior due to injuries, but it did not scare off the desperate Blazers.

Portland’s move backfired big time, as Pau’s surgically-repaired left foot never got better and he was waived by the team last November. Gasol has since confirmed that he is mulling retirement and will likely join the team’s coaching staff instead.

3. Brandon Roy

5-year, $82 million extension (2009)

Despite his unfortunate history with injuries, Roy still had a remarkable career for the Blazers. Pundits still argue that the 6-foot-6 stud could have been one of the best shooting guards of all-time, had he managed to stay injury-free.

Roy has given so much for the Blazers franchise that they still rewarded him with a massive contract despite their reservations about his health. But once he signed the dotted line, the injury bug just never left Roy alone.

The 3-time All-Star’s knees degenerated so much that he now lacks cartilage between the bones of both knees. This forced him to retire right about the time he was supposed to be in his prime.

Roy made a comeback in 2012, but couldn’t rerun to the Blazers since they used the amnesty clause for cap space flexibility. Adding more salt to the wound, Roy cost Portland $17 million when he played five games for the Timberwolves.

2. Evan Turner

4- year, $70 million (2016)

Turner was extremely fortunate that his contract year came around the same time the league experienced a spike in the salary cap. The 6-foot-6 guard was just one of the several underwhelming free agents who received bloated deals in the summer of 2016.

To be fair, Turner did enjoy a career resurgence under head coach Brad Stevens and the Celtics the season prior. He averaged 10.5 points, 4.9 rebounds, and 4.4 assists in limited minutes. Still, his play wasn’t deserving of the All-Star-type money he got.

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Portland gave him all the chance to replicate the same impact he had with Boston, but he failed to justify his huge payday. He was a durable player for coach Terry Stotts and embraced his reserve role. Even while starting 40 games in the 2017-18 season, the former 2nd overall pick still came up with mediocre production.

With a year left in his hefty deal, the Blazers swapped him from the Hawks for Kent Bazemore in 2019.

1. Darius Miles

6-year, $48 million extension (2004)

The electrifying Miles did show some promise when the Blazers first got him via trade midway in the 2003-04 season. His rejuvenated play perhaps made Portland brass think that he could finally live up to his ceiling as a premier talent straight from high school.

They gave the big extension afterward and Miles has proved he was worth the money at first. He averaged 12.8 points, 4.7 rebounds, 2.0 assists, 1.2 steals, and 1.2 blocks per contest in 2004-05.

As exciting as he was on the open floor, Miles wasn’t worth the headache off of it in the coming years. The 6-foot-9 forward infamously berated then head coach Maurice Cheeks after a filming session. He was then suspended for violating the league’s substance-abuse policy.

His numbers soon slipped and he figured in a career-threatening knee injury. Much like their scenario with Roy, the Blazers also took a salary hit when the supposedly retired Miles un-retired in 2008. His short stint with the Grizzlies added $18 million to Portland’s cap amount.