Over the course of its history, the Toronto Raptors have not been the top destination for big-name free agents. Some believe that while Toronto is a great city filled with the most passionate fans, players are not too ecstatic about playing in a different country, especially for Americans.

Despite this reality, the Raptors organization has managed to lure in some decent free agents, most of whom helped turn the franchise around.

5. Jamario Moon

Moon is a certified basketball journeyman. Prior to signing with the Raptors, he had spent almost a decade in various basketball leagues in the U.S. and in Europe. He even had a stint with the legendary Harlem Globetrotters.

With a wealth of experience and a load of talent, it's no surprise that Moon quickly attracted the Raptors' scouts in a three-day mini-camp in the summer of 2007. They offered him a two-year deal and right off the bat, Moon did not disappoint.

In his rookie year, he played 78 games (75 starts) and averaged 8.5 points, 6.2 rebounds, 1.2 assists across 27.8 minutes. He was named Rookie of the Month in February. And in the All-Star weekend, he laced up his shoes to join the Dunk Contest against Dwight Howard and Gerald Green.

At the end of the season, Moon was selected into the NBA All-Rookie Second Team.

4. Bismack Biyombo

Bismack Biyombo inked a two-year $5.7 million contract in the summer of 2015. This was after four mediocre seasons with the Charlotte Hornets (then Bobcats). As such, nothing much was expected from the seventh overall pick in the 2011 NBA Draft other than being a decent backup to then center Jonas Valanciunas.

But as the season progressed, Biyombo turned out to be a pretty good rebounder and a capable defender. In the regular season, the Congolese played 82 games (22 starts) and averaged 5.5 points and 8.0 rebounds (career high) across 22 minutes.

The peak of his lone stint with the Raptors came in the 2016 playoffs where he beefed his averages to 6.2 points and 9.4 rebounds in 25.3 minutes. Particularly in Game 7 of the second round against the Miami Heat, Biyombo logged in 17 points and 16 rebounds, which helped propel Toronto to its first-ever Conference Finals appearance in history. Against LeBron James' Cleveland Cavaliers, Biyombo set a Raptors playoff record with 26 rebounds.

Biyombo's time in Toronto came to a close in June 2016 when Biyombo opted out of his contract with the Raptors.

3. Anthony Parker

Anthony Parker was one of the top stories of the 2006-07 season. After all, he was making his return to the NBA after an unsuccessful stint almost 10 years earlier. The difference between then and his NBA comeback was that Parker was a decorated basketball player. He had won Euroleague MVP twice as well as two championships.

Right from the get-go, Parker proved that he does not only belong in the NBA, but he is a bona-fide starter in the best basketball league in the world. In his three seasons donning the Raptors' jersey, Parker was a respected shooter from beyond the arc and from midrange. At one point, he even led the team in 3-point field-goal percentage and free-throw percentage.

In his first season with the Raptors, he ranked fourth in 3-point percentage in the entire NBA. With Parker in the fold, the Raps clinched their first-ever division title. They also qualified for the playoffs for the first time in five years.

2. Jose Calderon

Prior to joining the Raptors, Calderon was already a decent playmaker in Europe. He wasn't a superstar, which is why there wasn't much hype surrounding his signing. But as the years progressed, Calderon's playmaking talents became more apparent to critics.

In eight seasons with the Raptors, the Spaniard averaged 10.0 points and 7.2 assists across 28.4 minutes.

In addition, Calderon was usually near the top of the assists-to-turnover ratio rankings, which is a great testament to his efficiency. He also developed into a deadly 3-point shooter and shot as high as 46.1 percent in one season. As of this writing, Calderon ranks second in assists (3,770) in Raptors' history, third in assists per game (7.2), and first in free throw percentage (87.7).

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Calderon also twice had 19 assists in a game, which was the Raptors record until Fred VanVleet had 20 assists in a game in 2023.

Without a shadow of a doubt, Calderon was a major steal from the free-agent market. It's unfortunate that Calderon joined the Raptors while they were still on rebuild mode. Nevertheless, the Spaniard made the most of his stint in the city of Toronto.

1. Fred VanVleet

For a team that has struggled to land big names in free agency to big contracts, it's fitting that it's greatest free-agent signing was for an undrafted free agent. VanVleet was an undersized point guard coming out of a mid-major college at Wichita State, so he from the beginning, he had to battle for his roster spot.

VanVleet spent much of his rookie season in 2016-17 in the NBA Development League. He earned a full-time roster spot his second season and became a key member of the rotation when the Raptors when the NBA title in 2018-19. He averaged 14 points per game in six games of the NBA Finals.

The next season, VanVleet earned the starting spot for the defending champs. In the four seasons since, he averaged 19.3 points, 6.7 assists and 1.8 steals per game. VanVleet even received the ultimate honor of a bid to the 2021-22 All-Star Game in which he scored six points.

He is once again a free agent after VanVleet opted out of his contract with the Raptors. However, there is still some hope VanVleet will return to the Raptors.