After another disappointing season in 2022-23, the Toronto Raptors will be looking to make changes to build toward another run for an NBA title. The changes began with the Raptors firing head coach Nick Nurse. They then addressed a big need by drafting sharpshooter Gradey Dick in the NBA Draft. However, losing Fred VanVleet certainly hurt after he signed with the Houston Rockets as a free agent.

While the Raptors have had success with free agents before, that hasn't always been the case. Hopefully, they can learn from those missteps. In 2023, the Raptors have signed Jakob Poeltl and Dennis Schroder, but it's too early to judge the merits of those free-agent contracts. Let's take a closer look at the five worst free-agent signings in Toronto Raptors franchise history.

5. Hakeem Olajuwon

Hakeem Olajuwon is considered by many as one of the best big men this game has ever seen. He was a legend with the Houston Rockets, garnering Rookie of the Year honors, 12 All-Star call-ups, a season MVP, two Finals MVP's, and two championships, to name a few.

Not many, however, know or remember that Olajuwon actually retired as a Raptor. In the summer of 2001, at 38 years old, the 7-foot center signed a lucrative three-year, $17.4 million deal via a sign-and-trade. This was obviously not something Olajuwon could turn down, and for their part, the Raptors actually believed that the decorated big man could help them make a run for the title.

That dream simply wasn't to be, with Olajuwon averaging 7.1 points, 6.0 rebounds, 1.2 steals, and 1.5 blocks in 22.6 minutes per contest. He didn't even bother suiting up for the final two years of his deal with the Raptors, but he still made sure he would collect the remaining $12 million owed to him.

4. Jason Kapono

In the summer of 2007, the Raptors were in need of a guy that could space the floor in order to give star big man Chris Bosh more room to operate down low. Who better to fill the need than the reigning All-Star Three-Point Contest champion in Jason Kapono. It seemed like a match made in heaven with the 6-foot-8 swingman becoming an unrestricted free agent that same summer. Toronto pounced to the tune of $24 million for a four-year contract.

To cut the long story short, Kapono failed to live up to expectations. In two years with the team, he averaged 7.7 points, 1.8 rebounds, and 1.0 triples per game. The Raptors decided to pull the plug on the Kapono experiment mid-way through his four-year deal, sending him off to the Philadelphia 76ers in exchange for Reggie Evans.

3. Landry Fields

What makes the Landry Fields signing so intriguing is the fact that the Raptors never really wanted him anyway. It was all part of a ploy that backfired in the face of former general manager Bryan Colangelo.

So here's how it goes. In the summer of 2012, the player the Raptors were really gunning for was back-to-back MVP winner and Canadian national Steve Nash, who had become a free agent. Toronto's main competition were the New York Knicks. Fields, then a coveted up-and-comer who also happened to be a restricted free agent, was a player that New York valued. The Raptors banked on this notion, and offered Fields a three-year, $19.5 million deal under the assumption that the Knicks would match the deal, and thereby not leaving them with sufficient cap space to try and sign Nash.

Well, the Knicks called their bluff, and they let Toronto sign Fields, who played three unproductive years with the Raptors before (forcibly) retiring from the NBA at just 26.

2. DeMarre Carroll

Even before DeMarre Carroll signed with the Raptors in 2015, he was already a bona fide NBA journeyman. Playing in five different teams in the span of five years, it was with the Atlanta Hawks where the 6-foot-6 forward would finally find relevance. After a breakout contract year with the Hawks where he averaged 12.6 points, 5.3 rebounds, 1.7 assists, 1.3 steals, and 1.7 3-pointers, Carroll instantly became a hot commodity in the free agent market.

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Toronto offered the former Vanderbilt standout a huge $60 million, four-year deal that summer, to which Carroll gladly obliged to. Unfortunately for the Raptors, Carroll's production would dip in the two years he was with the team. In 2017, Toronto had enough of Carroll, trading him away to the Brooklyn Nets along with a first-round and a second-round pick for none other than Justin Hamilton.

1. Hedo Turkoglu

The Carroll deal was bad, but the Hedo Turkoglu signing in the summer of 2009 could make that decision look like a smart one.

Turkoglu had a tremendous season with the Orlando Magic in 2008-09 and appeared to be exactly the player the Raptors needed to bring in to help bolster the squad. Aside from his above average talent level — Turkoglu was the 2008-08 Most Improved Player winner — Toronto also brought him in as part of a ploy (yes, another one) to try and desperately convince Bosh to sign an extension with the team.

This cost them $53 million for five years (sign-and-trade). In his solitary season for the Raptors, the Turkish national averaged 11.3 points, 4.6 rebounds, 4.1 assists, 0.7 steals, and 1.5 triples per game. This actually wasn't all that bad, but it certainly wasn't worth the $9 million he was paid that year.

To make matters worse, Bosh ended up leaving anyway, opting to sign with the Miami Heat the following summer. This meant the Raptors had to rebuild, and they quickly rid themselves of Turkoglu, shipping him off to the Phoenix Suns just one year after signing that humongous deal.