Damon Stoudamire, Tracy McGrady, Vince Carter, Chris Bosh. Arguably the four best Raptors in franchise history by the turn of the decade. All four have one thing in common: They never spent more than seven years in Toronto.

Rewind back to the 2009 NBA Draft, the Raptors selected DeMar DeRozan with the 9th pick, and by doing so, selected another franchise great.

Now, seven seasons later, DeRozan is leading the Raptors to their third straight playoff berth. Following his rookie contract, DeRozan signed a four-year, $40 million extension with a player opt-out in his final year. At the time, the extension was a risky move by then-GM Bryan Colangelo, as DeMar’s game was still developing.

DeRozan quickly outperformed his new contract, making the All-Star team for the first time during the 2013-14 season. DeMar hasn't looked back, averaging over 20 points per game and becoming the team's clear go-to guy on offense.

The question at hand is whether DeRozan is worth the max deal he’s looking for. These days, a player under a max contract needs to fulfill certain criteria.

Is he a fit for the team’s system: DeRozan has only suited up for one NBA team in his career, and the Raptors have built a system under Dwane Casey that caters to DeMar’s offensive skillset. While many criticize the limited range on his jumper, DeMar is one of the most efficient scorers in the league. He leads all Eastern Conference guards in drives to the basket per game and gets to the free throw line 8.3 times per game. That places him among the best two-guards in the league alongside James Harden (10.1) and Jimmy Butler (8.2). DeMar is also one of the best in the league in the pick and roll game.

DeMar DeRozan ranks 2nd in the NBA in pick & roll scoring efficiency behind only Steph Curry and 7th in pick & roll scoring (1st among SGs). — Synergy Sports Tech (@SynergySST) January 14, 2016

Does he play a key role for the squad: DeRozan is the go-to scorer for the Raptors. Not only that, but he’s improved his off-the-ball game through his career, and is now contributing over 4 assists per game. This is an easy one to check off the list.

Does he keep his composure in clutch situations: Not just keeping his composure, mind you, but makes the right plays in late-game situations. DeMar has proven time and again that he’s the guy Casey wants with the ball in his hands with the clock ticking down.

Is he a leader: Kyle Lowry has played a major role as the team's vocal leader. DeRozan on the other hand, is more of a quiet guy. But don't misinterpret his silence for a lack of influence. DeMar leads by example on the court, and keeps teammates motivated in the locker room.

His relationship with the city: This really isn't a main focus when teams target someone with a max contract, but it comes into play when you're trying to give your player a new deal. DeMar has always been an active part of the community, and has been adamant about calling Toronto his second home:

“Toronto is all I’ve known, honestly. I came in, 19, everything was completely new for me. I appreciated the support, the love,” DeRozan, 26, told Yahoo. “I treated it like home since then.”

DeMar's feelings for the city were reciprocated a couple of years ago, to the point that he was able to avoid a change in the Raptors' colour scheme. Kyle Lowry explained on a previous edition of The Lowe Post podcast how DeRozan fought to keep the Canadian colours with the team:

"We was supposed to change everything. We was supposd to go black and gold everything"

"And DeMar was like, he didn't want to do that, because he's been here with the red and white - and they're Canadian colours.

Listen, our colours are red and white. This is what it is. Let's leave it how it is. We're Canada's team"

So for anyone out there who isn't a fan of the black and gold unis, you know who to thank for not making that a permanent thing.

The numbers show that DeRozan is in the very select group of top shooting guards in the league, and with the current fluctuation of the salary cap, he's absolutely worth the price tag he's asking for. Jimmy Butler recieved a 5-year, $95M contract following his breakout season. DeMar has been playing at that level for two more seasons.

Toronto has a hard enough time bringing in top tier players through free agency, and is a team that has to build from the draft and through player development. DeRozan is one of the best finished products the Raptors have groomed, and re-signing him should be top priority in the offseason.

More from Yahoo Canada Sports: