In 29 seasons in the NBA, the Toronto Raptors have never been a major player in free agency. The Raptors have built great teams through the draft and via trades, but have never been a magnet for major free agents. What the Raptors have done in free agency, however, is find under-the-radar free agent signings like Jose Calderon and Fred Van Vleet who massively outplay their initial contracts.
For the sake of this list, we'll look at the seven best free agent signings in Raptors franchise history by only including true outright free agent signings and not players who were drafted or acquired via trade and then re-signed by the team.
Without further ado, the top free agent signings in Toronto Raptors franchise history:
7. Jarrett Jack, PG
The 2009 offseason was a disastrous one for the Raptors, as Hedo Turkoglu and Andrea Bargnani were both signed for over a combined $100 million in total salary. The only saving grace was that Bryan Colangelo also signed Jarrett Jack to a 4-year deal worth $19.5 million, which ended up being a bargain in the one full season Jack played in Toronto.
Jack was a part-time starter for a 40-42 Raptors team that had a top-5 offense with him in the backcourt. Jack averaged 11.4 points and 5 assists per game on great shooting splits (48-41-84) while sharing the point guard duties with Jose Calderon.
The Raptors, unfortunately, couldn't guard anyone and were dead last in defensive efficiency with Calderon, Turkoglu and Bargnani playing major minutes. Toronto ultimately missed the playoffs, and star big man Chris Bosh took his talents to South Beach the next year. Jack would ultimately get dealt to New Orleans for Jerryd Bayless, but he was one of the first sought-after free agent acquisitions by Toronto to actually pan out.
6. Jamario Moon, SF
Jamario Moon took one of the most unique paths to the NBA in league history. After playing one season of junior college basketball, Moon declared for the draft…and wasn't drafted. Moon ended up bouncing around all kinds of leagues in America, including the CBA, USBL, ABA, and WBA.
The breakthrough for Moon came at age 27, when he impressed the Raptors in a three-day tryout camp and earned a spot on the roster. Incredibly enough, Moon ended up starting 75 games in his rookie season, quickly enamoring himself to Raptors fans with his incredible athleticism and leaping ability. With Moon as a rookie starter, the Raptors made the playoffs, snapping a five-year postseason drought.
Although Moon would only play in Toronto for two and a half seasons, he was able to represent the Raptors at the 2008 Slam Dunk contest and was a true diamond in the rough signing that paid major dividends.
5. Chris Boucher, PF
Chris Boucher is another player who took an unusual path to the NBA, going undrafted out of Oregon and not making his debut until he was 25 years old with the Golden State Warriors, where he played in exactly one minute of one game for the 2017-18 championship Warriors squad.
Fortunately, that wouldn't be the end of the road for Boucher. Masai Ujiri would eventually convert Boucher's two-way contract into a full one…and Boucher would win yet another championship in his second year, despite rarely playing for the Raptors.
While Boucher's championship streak had to come to an end, he's blossomed into a productive rotation player for the Raptors in his five seasons with the team, 9.1 points, 5.4 rebounds and 1.1 blocks in 18 minutes a game. Finding inexpensive production is always difficult, but Boucher provided multiple seasons of above-average play at his position for some of the best Raptors teams in franchise history.
4. Bismack Biyombo, C
Bismack Biyombo only played a single season in Toronto, but he provided major defensive production for the bargain price of just $3 million a year on a 56-win team that went to the Eastern Conference Finals.
Biyombo, who was only 23 at the time, averaged 5.5 points, 8 rebounds and 1.6 blocks in just 22 minutes a game, helping to solidify Toronto's frontcourt rotation while providing the defense and toughness Dwane Casey's team needed.
While the one-year deal worked out for Toronto, it worked out even better for Biyombo, who parlayed his big postseason performance into a massive deal worth $72 million the next offseason. Biyombo never lived up to that contract, as his lone season with the Raptors was the best of his career.
3. Anthony Parker, SG
Anthony Parker came to Toronto after playing six seasons overseas in Italy and Israel as a 31-year-old free agent. Expectations were relatively modest for the two-time Euroleague MVP, as Parker was signed to a 3-year deal worth $12 million.
But Parker exceeded every expectation for the Raptors, becoming a full-time starter right from the jump and providing incredible floor spacing for the rest of the roster. Parker shot an incredible 42.4 percent from behind the arc in the three seasons with Toronto, averaging 12 points and 4 rebounds a game.
The Raptors weren't able to advance out of the first round during his time with the team, but Parker was a quality starter who could shoot and defend on a cheap deal. This may feel high for him on a franchise free agent ranking list, but Parker was a very good player who didn't take anything off the table when he played and was a bit ahead of his time as a 3-and-D wing.
2. Jose Calderon, PG
Jose Calderon is one of the best players in Toronto Raptors franchise history, and signed with the Raptors as a free agent from Spain in 2005. After battling for minutes with T.J. Ford early in his career and struggling with his shot, Calderon kicked it into high gear this third year in the league, averaging over 11 points and 8 assists a game on incredible shooting splits (52-43-91), joining the “180 club” reserved for the league's very best shooters.
Calderon was a little ahead of his time, though, and his efficiency shooting the ball wasn't yet fully appreciated. Despite being one of the league's best shooters and table setters, the Raptors kept trying more athletic but less skilled players at the position instead of fully handing the offensive keys to Calderon.
Despite all that, Calderon remained incredibly effective, putting together eight great seasons with the Raptors. Jose Calderon is second all-time only to Kyle Lowry in assists for the Raptors, and ranks either right at or very near the top in multiple other categories on Toronto's all-time leaderboard. This is about as good as it gets from a bargain bin free agent signing.
1. Fred Van Vleet, PG
That is, of course, except for Fred Van Vleet. The undrafted guard out of Witchita State grinded his way into a substantial role for the Raptors, culminating in an incredible postseason run for the 2019 NBA Champions, where he averaged 14 points a game and burst onto the scene as one of the most underrated two-way guards in the league.
Van Vleet would later go on to become an All-Star in the 2021-22 season, an astonishing accomplishment for an undrafted guard who made the league minimum his first season in the league.
After seven terrific seasons where he defied all logic for what an undrafted free agent signing could do, Van Vleet cashed in when the Houston Rockets signed him to a 3-year deal worth $130 million. Fred Van Vleet is still the only free agent signing in Raptors franchise history to make an All-Star game while signed with the team. Like Jose Calderon, Moon and Parker before him, Toronto's investment in “untraditional” rookies paid off majorly for the franchise on this one.
The Raptors probably don't win a championship without signing Fred Van Vleet as a free agent back in 2016, making him by far the best free agent signing in Raptors in franchise history.