Agent X is an active and certified NBA Agent with clients who have played on Masai Ujiri’s teams in both Toronto and Denver. He’s also Sportsnet’s NBA Insider, and you can check out his previous articles here.



Moving into this summer it’s obvious Masai Ujiri will be faced with some interesting decisions that will shape what the Raptors look like for years to come.

One of the main things you have to respect about Masai is that he never rushes a decision. He decides things on his terms, and that patient approach isn’t one you see from a lot of NBA franchises. All too often teams will get swept up in emotion and simply react. Masai has shown an ability to wait situations out, and it’s resulted in some very advantageous deals for his teams. The Carmelo Anthony trade he orchestrated while running the Denver Nuggets is a good example. An even better one would be his dealings with current Raptors head coach, Dwane Casey.

Many expected otherwise, but when Masai first took control of the Raptors, he delayed a decision on Casey, who had been hired by the previous regime. When Masai took the job, there was a natural window to change the coach, as new GM’s often try to do. Instead, he mostly kept the team intact. Aside from the Rudy Gay deal with Sacramento, the core of this team is the same as the one he inherited when he took the job. He’s given it time to grow and develop, and his patience has paid off.

A lot of people don’t realize how difficult the process of hiring a coach in the NBA really is— especially the right coach. Because job security is rare in their field, coaches are conditioned to the hiring process. They interview well and portray themselves in a certain light in order to get jobs, but once they’re handed the reigns, their true natures always (and I mean always) come shining through.

Experienced GMs realize this and it’s why they typically take so long during coaching searches. You will not find a GM who regrets anything more than a bad coaching hire.

In Masai’s case there are clearly no regrets. He gave Casey the time and space to really find his stride and build the team the way he wanted to, and the coach is now being rewarded for it with his second contract extension.

Masai is an interesting guy. He’s one of the most popular GMs in the NBA, but he can seem distant at times; you’d be hard pressed to find a lot of people who consider themselves to be truly close with him. That applies to both people like me who have worked with him for years from the opposite side of the fence, and those that have worked for him in the front office. This is something he does by design.

For the most part, Masai is a man of few words—until he isn’t. A typical interaction with him will begin with a generic greeting. After that you never know if he’s simply going to walk away or corner you for 15 minutes to talk about a subject of his choice—a potential new signing, contract details, information on happenings around the league, etc. If he does this you better have answers on the questions he’s asking because he is going to be very direct.

But the reverse is not true: He will not allow himself to be pinned down on anything.

If you try to approach Masai on your terms and corner him, he won’t let you. He’s flat-out just walked away from me on things. At the time it was annoying, but I’ve come to appreciate in a way. He absolutely wants to keep an air of mystery about himself and the Raptors’ business. Looking back at those interactions now, and considering his success, it’s something you have to respect.

I’ve enjoyed every interaction I’ve had with Masai, whether in-depth business dealings and contract negotiations (I’ve had multiple people play for him in both Denver and Toronto) or simply running into him and talking about everything but work. But as most people will tell you he does not get in-depth or particularly detailed in everyday interactions, and pressing him to do so makes him visibly uncomfortable.

So it can be hard to get a read on him. But whether he lets on or not, you know he’s going to be extremely active this summer.

Free agency is going to be an absolute frenzy this year. There are marginal players in this league who are going to secure contracts that will truly shock people, and a great many GMs are going to be very leery of setting a market for a role player.

Toronto might very well lose Bismack Biyombo, who I’m hearing could be the first contract signed this summer that really surprises people. After the success the Raptors had in the playoffs, the market is just taking off for Bismack. Once he comes off the board, it will be interesting to see what the Raptors do.

It would seem securing DeRozan to a long-term deal is a no-brainer, but anyone who knows Masai knows he has something planned that no one else sees. In other words, he is going to take a swing for the fence. Whether it’s Kevin Durant, Al Horford or someone else, Masai will take a run at a player via free agency or trade that will surprise people in the industry.

The Raptors are in a tough position. Sure, they had by far the lowest payroll of the NBA’s Final Four this year. But that was because two of their rotation players—Terrence Ross and Jonas Valanciunas—were on rookie contracts. With their extensions kicking in at the start of next year at a combined $28 million, plus DeMar’s new contract, Toronto’s salary commitments are going to greatly increase.

Team success in the NBA comes at a cost for ownership—coaches, players and staff all expect to be compensated.

The Raptors played the maximum amount of home playoff games possible without making the Finals this year, and everyone involved is going to expect to share in that success. Moving forward, Masai will have to find a way to use the limited resources (on paper at least) Toronto has to add pieces in free agency that will help this team take the next step.

One thing is for sure: When it’s time for him to step to the plate, Masai will swing for the fences.