As a long time Toronto Raptors fan living in Toronto, it has been tough to see players leave that we drafted and developed. Damon Stoudamire, Marcus Camby, Tracy McGrady, Vince Carter, and Chris Bosh to name just a few.

In the June of 2009 at the NBA Draft, the Toronto Raptors selected DeMar DeRozan with the 9th overall pick in the first round and the city welcomed a 19 year-old kid out of Compton, California to the beautiful city of Toronto, better known simply as the Six these days. In 2009, Toronto was a shell of what it is today as the Raptors had finished with a record of 33-49, missing the playoffs for the ninth time in franchise history after experiencing consecutive playoff seasons.

When DeMar was drafted out of the University of Southern California, no disrespect to him but I knew his name more so due to the fact he was that dude playing at USC with Lil’ Romeo, the son of former rap star Master P (who coincidentally played in six preseason for the Toronto Raptors leading up to the 1999-2000 season), not as the “next Vince Carter” that some journalists were saying due to the dude’s immense athletic abilities.

His first season with the Raptors was difficult as we had the wrong mixture of players on our team with Bryan Colangelo at the realm as General Manager and the questionable roster decisions made by the organization reflected the final result of the team’s season by missing the playoffs for another season. That 2009-2010 Raptors team remains to date one of my least favourite Raptors team ever with the presence of the lottery mistake embodiment that is Andrea Bargnani, as well as the presence of the ridiculous Hedo Turkoglu and his massive contract. Following another poor season under Jay Triano in 2010-2011,management decided upon a front office overhaul with a coaching change that offseason and the hiring of a new GM, the notorious Masai Ujiri, at the conclusion of the 2011-2012 season.

In the beginning of the 2012-2013 season, the second season under current head coach Dwayne Casey, the Raptors inked DeRozan into a 4 year extension with an annual salary of $9.5M with no incremental yearly raises but with incentives to possibly raise it to $10.5M and a player option for the fourth year. Many analysts believed that it was a poor decision made by the Raptors at the time and on the day that the deal was announced, Sports Illustrated’s Ben Golliver said it best when the first sentence of his article reporting on the extension read, “Sooner or later, there could be some buyer’s remorse on this one.”

Well, it’s safe to say that the Raptors and DeRozan have proven these critics wrong as the first three years of the extension resulted in three Atlantic division crowns, three consecutive playoff appearances with home-court advantage, matching or setting franchise records in team wins in a season, and an overall record of 153-93 (62.2% winning percentage). Although the playoffs have been another story on its own, DeRozan has proven his worth in the NBA as an elite level wing player and will be demanding a max or near-max contract this summer.

With the increase of the NBA salary cap in the 2016-2017 season to approximately $90M, the max contracts for a player with seven years of experience in the league like DeRozan will be $25.3M with annual increases. As the Raptors do own his Bird Rights, they are eligible to offer him a fully loaded five-year max contract at approximately $146.95M with a yearly salary increase of 7.5%. The five-year max contract will have a starting salary of $25.3M and his salary by the final season will be approximately $33.8M. Other suiters will be able to offer him a four-year max contract at approximately $108.24M with a yearly salary increase of 4.5%, which will mean that although he receives the same $25.3M in the first year of this four-year extension, his salary by the final season will be approximately $28.9M, a notable difference in salary and security. Something vital to note is that certain teams, such as the Orlando Magic who play in the state of Florida, have the advantage of playing in states with no income tax which will be very attractive and there will also be numerous other factors including the possibility of playing for his hometown in Los Angeles and taking over the reigns of the Lakers from the recently retired Kobe Bryant.

Although the playoffs have not helped DeRozan’s free agency value, I truly believe that it will not matter and he will sign a max contract in the offseason as he will just be turning 27 years old at the beginning of the next season, entering his physical prime. I do believe that he will resign with Toronto for the full five-year max with an opt-out clause after his third season, due to the simple fact that $38M is a lot of money and as long as the commitment from the Raptors is still there, it is in the lines for DeRozan to join Lowry as consecutive star players that the Raptors were able to retain through free agency.

What are your thoughts?