If the Toronto Raptors are unable to sign Giannis Antetokounmpo, it could mean the end of Masai Ujiri’s tenure in the Six.
Masai Ujiri joined the Toronto Raptors seven years ago and within that timeframe has made more of an impact than any other individual in franchise history.
From trading Andrea Bargnani, screaming “F***, Brooklyn”, acquiring Kawai Leonard, and winning an NBA championship, the Toronto Raptors executive has been a brilliant decision-maker. Since being hired, the team has yet to miss the playoffs and will not be doing so anytime soon.
His hiring was a breath of fresh air and brought hope to an organization that was struggling. Before joining the Toronto Raptors, the team had only won one playoff round in 18 seasons and although the fan-base was loyal, it wasn’t as strong as what it is today.
In terms of accomplishments, Ujiri has essentially done everything an executive aspires to. He’s drafted and developed great talent (Pascal Siakam, OG Anunoby), re-signed key players in Kyle Lowry and Fred VanVleet, hired NBA Coach of the Year Nick Nurse, and put together a championship team in 2018-19.
He’s done more in seven seasons with Toronto than most executives achieve in an entire career. However, there’s still one thing left to do: attract a big-name free agent to Toronto.
Signing Antetokounmpo will be the exclamation point on Ujiri’s career
When you look back at the history of the Toronto Raptors franchise, there’s one thing that is constant. The team has never able to attract big-name free agents. Even when the team drafts and develops a superstar, it’s hard to believe that the player actually wants to re-sign in Toronto.
The Toronto Raptors have done a better job over the past few years in re-signing players, thanks to Ujiri. For example, re-signing DeMar DeRozan was a huge deal (before shipping him out to San Antonio for Leonard). Even re-signing Kyle Lowry, Pascal Siakam and most recently Fred VanVleet were big wins for the franchise.
However, history has shown us that “X Player” typically wants to leave. Whether it’s Vince Carter, Chris Bosh, Kawhi Leonard, Danny Green, Serge Ibaka, or Marc Gasol walking away via free agency or trade, most of the time the player doesn’t want to stay in Toronto.
Not only is it hard to keep a player, but it’s also even harder to bring one to Toronto. Although all of these players seem to love the city, the idea of playing in a different country still doesn’t seem ideal. Maybe it’s the tax or it’s just the cold, but recruiting a superstar to play for the Raptors has been an impossible task for the franchise.
With the “Greek Freak” set to become an Unrestricted Free Agent at the start of the 2021-22 season, you know Ujiri will do whatever he can to sign him. Whether it’s renaming Danforth Avenue, “Antetokounmpo Avenue,” or offering him a partnership with every company in Canada, Ujiri’s going to pull every string in order to cross “signing a big-name free agent” off his executive bucket-list.
If everyone isn’t aware already, Ujiri is also set to become an Unrestricted Free Agent at the beginning of the 2021-22 season and I truly think the “Greek Freak” signing will have an impact on whether he stays or goes. If he can sign Antetokounmpo and bring him north, he’ll stay and try to win another few titles in Toronto.
However, if he can’t get Antetokounmpo to play in Toronto, he’ll probably never have as good of a chance at signing another big-name free agent. Acquiring the “Greek Freak” isn’t a pipe-dream based on the two’s connection. Ujiri helped Antetokounmpo’s family emigrate from Nigeria to Greece, if he’s not going to convince Antetokounmpo, it’s probably time to move on.
If they fall short and Antetokounmpo signs with another team or stays with the Milwaukee Bucks, Ujiri will probably let his contract expire and pursue another team himself, with a bigger challenge and opportunity. Who knows where that opportunity may present itself right now, but I’d have to think that his biggest quest is getting Giannis than figuring out what his personal future holds.