Masai Ujiri to the Knicks? The case for and against

Toronto Raptors president, Masai Ujiri, is being pursued by James Dolan and the New York Knicks. What does Ujiri stand to gain from a move to New York City?

If we know one thing about Masai Ujiri, it’s that he loves challenges. He relishes them and embraces them. Last season, Ujiri traded DeMar DeRozan, a beloved soldier of the north, for a disgruntled, homesick mercenary carrying the name Kawhi Leonard. That trade made the Toronto Raptors immediate title contenders, precisely the challenge Ujiri was up for. With LeBron James out west leading a rebuilding-ish Los Angeles Leakers team, the time was right to make a big splash, and Ujiri did just that.

The challenge of establishing a relationship with Leonard was another uphill battle for Toronto’s president, but Ujiri persevered and soon found himself rolling through Toronto’s sunny streets, Larry OB trophy in hand.

Challenge complete.

Masai Ujiri, as he promised, won in Toronto. He built a winner in Canada and did so with class and humility. Aside from overseeing the Raptors, Ujiri is an advocate for women in professional sports.

Toronto’s front office is among the most diverse and tightly-knit as you’re going to find in modern-day sport, and it all starts with the man at the top, which brings me to the New York Knicks: a team desperately in need of a leader.

"Have you ever met someone who didn’t come from a woman?– Masai Ujiri"

What was by all accounts supposed to be a relatively quiet trade deadline week for Toronto has suddenly gotten very loud. We can all thank the Knicks “level-headed” owner, James Dolan for the noise. Fresh off firing team president Steve Mills, Dolan reportedly has tabbed Ujiri as Mills’ ideal replacement.

But does Dolan’s offer – a chance to live in New York, to further grow the Giants of Africa program all the while turning around one of the league’s most iconic franchises – make sense for Masai Ujiri?

Well, it both does and doesn’t.

The case to leave

“You either die a hero or live long enough to see yourself become the villain,” is a quote I often reference in life. It’s spoken by Harvey Dent aka Two-Face in the movie The Dark Knight.

This quote can be applied to Ujiri’s current situation in Toronto – if you’re Masai, what else is left for you to do in Toronto? He’s established a winning culture in Toronto and got what was a lost franchise back on a clear path for sustained success. Is there really anything else left to accomplish “up here”? Has Ujiri reached the summit of the six already? Is there nowhere to go but down? It may not be clear to Raptor fans right now, but anything besides another title will feel like a failure.

For a man with Ujiri’s aspirations, moving to New York would open so many doors off the court. First, the United Nations has a big presence in NYC, and that’s something Ujiri could (and would) leverage as he seeks to grow the Giants of Africa program. And of course, remember what Masai Ujiri is most attracted to – challenges.

The ship captained by Mr. James Dolan has been lost at sea for decades. Before Ujiri, you could say the same thing about Toronto’s hypothetical vessel. Having succeeded in altering the Raptors’ course, the time seems right for Masai to set his sights on another challenge, perhaps one involving bringing the New York Knicks back from the dead. He does that, and Masai Ujiri truly has no equal in the community of basketball executives.

Now, for the other side of the coin – why should Masai Ujiri stay in Toronto?

The case to stay

There remains one thing on Masai Ujiri’s Toronto to-do list. Everything else has a checkmark beside it.

What started out as a culture-building exercise culminated in a title a year ago, and it was made possible by Ujiri’s decision to go out and acquire a superstar. Of course, I’m talking about Kawhi Leonard. Sorry, Danny Green.

Prior to the arrival of Leonard, Toronto hadn’t seen a superstar since Vince Carter. Both DeMar DeRozan and Kyle Lowry qualify as NBA “stars”. The same goes for Chris Bosh and 2005-06 Mike James – one of these things is not like the other one…

To date, Masai Ujiri has yet to lure a superstar free agent to Toronto. He’s re-signed the likes of DeRozan and Lowry (twice) but has never returned home from the free-agent market with a larger-than-life star.

Enter Giannis Antetokounmpo – provided he doesn’t sign an extension this offseason, Antetokounmpo will become a free agent in 2021 and is sure to generate a little more than some interest on the open market. Every team (no exceptions) will be interested. Few will get a seat at the negotiating table, though.

If Ujiri is still in Toronto, best believe he’ll be at the head of the table.

If Masai were to ultimately be crowned the winner of the 2021 Giannis sweepstakes, he could honestly say that he’d done it all in Toronto. From there, he could move on to bigger and better things, such as rebuilding the New York Knicks. But if he leaves before even trying to attract Giannis up north, that will always be a teeny, tiny blemish on an otherwise spotless Raptors tenure.

A big decision awaits Masai Ujiri in days and months to come – two franchises posing two distinct challenges.

Which one will the giant of Africa choose to tackle?