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I expressed my concern yesterday when the possibility of the Raptors and DeRozan coming to an extension agreement before the midnight deadline was only a report about progress being made in the talks, but in all honesty, I wasn’t that worried about it.

The way I saw it, if the Raptors locked up DeRozan last night, while all he had on his NBA resume were three so-so seasons where his offensive efficiency decreased and where he failed to show that he can be anything other than an inefficient scorer, surely they’d be locking him into a cheaper than expected extension, maybe even a bargain!

Think again. Four years, a reported $38 million guaranteed, with bonuses that can take the perplexing contract north of $40 million. Inexcusable.

While the heat’s grown around Bryan Colangelo over the last few years, I’ve remained relatively supportive. There were obvious experiments gone wrong (namely Jermaine O’Neal and Hedo Turkoglu) during the latter part of the Chris Bosh Era, but Colangelo (with Ed Stefanski beside him as a safeguard) seemed to have really figured things out over the last year or so.

Landing Steve Nash might have been a step back for the rebuild, but it still made sense for a lot of reasons. In the end, Toronto landed a point guard to move forward with to add to a potential franchise centre and a defence-first coach whose hire alone gave me reason to believe that Colangelo understood what was necessary to win in the NBA. I always knew the eventual final piece of landing a superstar would be incredibly difficult, but for now, it was hard to find much fault in Colangelo’s plan for the future.

And then yesterday happened.

I’ve heard a bunch of excuses from a bunch of fellow Raptors fans – friends, family members, coworkers, etc. – and none of them add up. I’ve heard about how hard of a worker DeRozan is, how committed he is to getting better, how young he still is and how the organization was anticipating DeMar might get an even bigger offer from another team as a restricted free agent in the summer, forcing the Raptors into a tough decision.

Well here’s the problem, effort and a desire to improve don’t win many games in the NBA. Sure, those are two traits you’d like your star players and others to have of course, but if you’re gambling on work ethic instead of talent and tangible results, you’re in trouble.

Yes, DeRozan is still a young player at 23, but in the world of pro sports, especially the NBA, he’s not thaaat young. I’m sure there are plenty of examples of raw players who blossomed later in their careers, but unlike with bigs, you can usually tell with wing players within their first few years as pros. And the ones that do develop slower still show some sort of consistent competency in more than one facet of the game.

Through three seasons, DeMar DeRozan is an exciting athlete that can score with a lot of touches, but hasn’t been able to score efficiently. I’m still encouraged by his developing post game, and as Oliver wrote yesterday before word of the extension broke, DeRozan’s time in the post can lead him down a path to becoming a more efficient offensive player. Unfortunately, it won’t change the fact that he’s a one dimensional player at that.

At 23, DeMar still can’t defend despite his athleticism and he can’t pass, or he just chooses not to. His rebounding is inconsistent at best and his jump shot doesn’t exactly scream “shooting” guard. For me to even be convinced DeRozan deserved a place in this franchise going forward, I wanted him to prove he could become a more efficient scorer and at least become average in other facets of the game in his fourth season.

Three mediocre seasons and an encouraging training camp/pre-season were apparently all the organization needed to not only be sold on the fact that DeRozan deserved a core role in the future, but that he was also on the verge of becoming a worthy $10 million per year player.

And that brings us to the last excuse for the contract, that Colangelo and co. probably thought another team would make him a $40+ million offer in free agency. My response? Good riddance!

If the current market in the Association deems that a player of DeRozan’s ability should earn nearly eight figures per year, then let another general manager pay him that money next summer. I’d rather overspend and spend even more than $38 million over four years on a player who can at least contribute to a winning core in the future as the second or third best player on said future team than overspend on a guy whose most positive attributes through three professional seasons are his work ethic and athleticism.

Furthermore, just because someone else is willing to overpay a certain player, it doesn’t mean that he’s necessarily worth it or even worth locking up at all. The question to ask isn’t “would another team give DeMar DeRozan $38 million over four years?” but rather “would a team serious about building a championship core for the future give DeRozan that money?” and I think we all know the answer to that question.

Under normal circumstances, I would have looked at last night’s heartbreaking loss as frustrating, but still a glimmer of hope of how good this team can be this season and more importantly, in the future. Instead, my frustration over the near buzzer beating loss, the latest in a string of those at home over the years, was compounded by my concern and frustration over the fact that DeRozan’s new lucrative contract will hinder this team’s chances of getting that much better over the next couple of years.

The Raptors should have had roughly $10 million in cap space next summer, with an amnesty option that could have taken that number to $15 million or more. Looking beyond even next summer, the team could have extended Lowry in the future with a sizable contract and still would have had plenty of breathing room going forward. With DeRozan’s contract soon to be on the books, the Raps might have little, if any, cap space next summer and might be capped out going forward once they extend Lowry, whose agent should be asking for max money with DeRozan at nearly $10 million (I’m only half kidding).

Lastly, to the abundance of fans and DeRozan supporters who will read this and vow to me that I’ll regret what I’ve written and that DeRozan will make me look foolish for writing it, here’s a newsflash for you: I hope you’re right. I hope I’m wrong. I yearn for Raptors success as much as anyone reading this, if not more. I like DeMar, I really do buy into his desire to make something of himself, I find his commitment to the city a breath of fresh air, and for the thousandth time, I find him incredibly easy to root for overall. Unfortunately, none of that means he was worth the money right now.

DeRozan isn’t going to be the only overpaid player in the NBA over the next four years and he certainly won’t be the last one to benefit from a ludicrous deal. In addition, Bryan Colangelo and the Raptors won’t be the last ones to sign a questionable player to such a contract, and at the end of the day, between the amnesty clause, trades and whatever else is out there, the Raptors’ future cap situation probably isn’t as dire as I think it is or understand it to be.

But this is a management team and franchise that looked to have finally figured out the big picture, the end goal and more importantly, how to get there, and a fanbase that had finally started believing we could see some light at the end of this dark, lonely tunnel. This unnecessary extension seems to be a step back for both in their quest to get to those destinations.