5 Best NBA Free Agent Signings of All Time for Toronto Raptors (2024)

Not every team in the NBA has the luxury of being a market that attracts the cream of the crop during free agency. Star players tend to choose big-market destinations such as Los Angeles, New York, Boston, and Miami over smaller markets that don't provide the same appeal as the aforementioned major cities. This requires the front offices of these small market franchises to be resourceful with what they have and attract not necessarily the biggest name but the best fit for their team.

Among those small-market teams, the Toronto Raptors historically haven't had the most success in the free-agent pool. However, essential signings have been made in the organization's history, eventually leading to the team capturing the franchise's first NBA championship in 2019. GIVEMESPORT will look at the five greatest free-agent signings for the Toronto Raptors.

1 Fred VanVleet (2016)

Contract: One-Year, $550,000

One of the greatest moves the Raptors have made during the ongoing Masai Ujiri tenure was the signing of Fred VanVleet in 2016. VanVleet entered the 2016 NBA Draft following the conclusion of an exceptional college career with the Wichita State Shockers, including a Final Four appearance in 2013. Although VanVleet's name is etched in the record books in Wichita State's program as the all-time assist leader, it wasn't enough for him to get drafted.

The Raptors took a chance on the 6-foot point guard, and it turned out to be the greatest free agent signing in franchise history.

VanVleet's career arc is the perfect example of the great internal development of a player within an organization. He barely played his rookie season but was thwarted into the rotation the next two seasons and helped formulate the identity of the Raptors' 'Bench Mob' second unit that wreaked havoc against the competition.

During the Raptors' championship run in 2019, VanVleet's contributions were imperative, especially in the final two series against the Milwaukee Bucks and the Golden State Warriors.

In the 2021-22 season, VanVleet reached his pinnacle as a player, being selected as an All-Star. Following the exit of Kyle Lowry, who was the heart and soul of the franchise for nine years, VanVleet embodied those elements as the team's lead guard.

However, the guard would leave in free agency in 2023 following a lucrative 3-year, $128.5 million offer from the Houston Rockets, which the Raptors simply couldn't compete with. Despite how the partnership between VanVleet and the Raptors ended, he is recognized as a legend in the city, and for good reason.

2 Jose Calderon (2005)

Contract: 3-Year, $7 Million

Before the Raptors were a powerhouse in the 2010s led by Kyle Lowry, there was another general leading the team at the point guard position who went by the name of Jose Calderon.

Toronto had a bad track record of enticing American players to play up north during the early 2000s and elected to direct their focus on international players in hopes of finding the next Drazen Petrovic, Dirk Nowitzki, etc. There were many misses throughout the implementation of this philosophy, but Calderon turned out to be a diamond in the rough.

The Rob Babco*ck era wasn't the prettiest in terms of roster construction, but the signing of Calderon was the greatest thing he did as a general manager. Calderon became a fan favorite for his steady play coupled with his high-level production.

The Spanish point guard played 525 games for the Raptors and was one of the most consistent lead guards in the NBA during that time. In the 2007-08 season, Calderon set the record for the highest free-throw percentage in a season with a 98.1 clip, converting 151 out of 154.

Calderon helped lead the Raptors to consecutive playoff appearances in 2007 and 2008, albeit first-round exits. In 2013, the Raptors would part ways with Calderon in a three-team trade, which sent him to the Detroit Pistons and brought Rudy Gay from the Memphis Grizzlies to Toronto.

3 Dennis Schröder (2023)

Contract: 2-Year, $25.43 Million

Although Dennis Schröder didn't play an entire season with the Raptors, there is a large populace of the fan base that believes he is the best free agent signing in NBA history. Following the departure of Fred VanVleet in the 2023 offseason, Toronto needed a replacement and leaned in the direction of Schröder, which turned out to be a great decision.

The addition of Schröder seemed to be a seamless fit as the lead guard for the Raptors in the 2023-24 season. His relationship with head coach Darko Rajakovic from his tenure with the Oklahoma City Thunder, made the connection between point guard and rookie coach a smooth one.

Although Schröder was a plus player on the court for the Raptors, the overall roster construction proved to be flawed for the second straight season, putting forth disappointing results. The front office decided to hit the reset button and blew up the main core, resulting in Schröder being traded alongside beloved Raptors', Pascal Siakam and OG Anunoby.

Despite the tumultuous non-basketball-related developments during Schröder's tenure, he proved to be one of the highest-value contracts that the Raptors have received from free agency in the franchise's history.

4 Bismack Biyombo (2015)

Contract: 2-Year, $5.7 Million

Another player that played just a sole season with the franchise, it can't be understated how impactful Bismack Biyombo was for the Toronto Raptors during the 2015-16 season.

Biyombo joined the Raptors after failing to live up to expectations with the Charlotte Hornets as the seventh pick in the 2011 NBA Draft. During the 2015-16 season, Biyombo was solid off the bench for Toronto as a rim protector and defensive anchor. However, it was in the postseason that Biyombo elevated his play tremendously.

The Congo native was outstanding during the 2016 NBA Playoffs and was one of the driving forces to the Raptors clinching their first Eastern Conference Finals appearance in franchise history.

His game three performance against the Cleveland Cavaliers in the Conference Finals stands as arguably his greatest game as a pro and one of the best performances by a big man in Raptors history. He finished with seven points, four blocks, and 26 rebounds, marking a franchise record.

Biyombo had a player option in the offseason following his tremendous playoff run, and with no surprise, declined it. The Orlando Magic gave him a 4-year, $72 million contract, which cut his tenure in Toronto short. However, he hasn't been able to replicate the same amount of success and impact in his years since leaving the Raptors.

5 Anthony Parker (2006)

Contract: 3-Year, $11 Million

In the realm of 'Linsanity' stories in basketball, Anthony Parker's career rejuvenation with the Raptors was one of the best storylines of the 2006-07 season. Brother of WNBA legend, Candace Parker, Anthony wasn't able to succeed at the same rate as his sister during his first stint in the NBA.

Originally drafted by the New Jersey Nets but dealt to the Philadelphia 76ers in the 1997 NBA Draft, Parker was never able to find his footing in the NBA. By his third season, he was out of the league and transitioned to the Euroleague, where he would dominate, winning the MVP award twice along with two championships.

Parker made a strong impression on the Raptors following a preseason exhibition against Maccabi Tel Aviv. The 6-foot-6 guard finished with 24 points, including the game-winning basket. The following season, Toronto picked him up and he immediately made an impact.

In Parker's first season in Toronto, he ranked fourth in three-point percentage throughout the entire league. The Raptors were clawing their way back to relevancy in the post-Vince Carter era, and Parker helped lead the Raptors to their first-ever division title in franchise history.

Parker would leave the Raptors in 2009 and join the Cleveland Cavaliers for three seasons before calling it quits on his NBA career.