Masai Ujiri enters most challenging season as Toronto Raptors head honcho

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A new hoops season begins in Toronto with a new head coach and a new vision.

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When any basketball conversation involving the Raptors gets initiated, it begins and ends with Masai Ujiri — the vice chairman and team president better known as a risk-taker who has had his share of hits and misses in reshaping rosters when change is required.

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During his tenure as the club’s head honcho, Ujiri has parted ways with two head coaches.

When many were clamoring for an experienced face to replace Nick Nurse, Ujiri decided to hand over the coaching reins to Darko Rajakovic, a rookie who is best known for his ability to develop players.

“To watch us play this year was not us,” Ujiri said when reflecting on 2022-23, which ended in a home loss to the Chicago Bulls in the play-in tournament. “I did not enjoy watching this team play. I think that spoke loud and clear to everything that went on.

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“You could see it throughout the year. There was never that full excitement. There was never that full spirit. There was never that feel of togetherness. We all saw it. You all saw it.

“This year wasn’t us.”

Ujiri did what any executive would do by turning the page. To his credit, there has never been any reluctance by Ujiri to initiate change, be it behind the bench or on the floor.

That being said, the changes he made this off-season speak to a team that remains very much in flux.

He’ll get a glimpse of the kind of impact his new head coach will have beginning Wednesday night, when the Raptors tip off their season against visiting Minnesota.

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There was no joy in Raptorland last season, one Ujiri conceded featured too much selfish play.

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A more engaged Scottie Barnes, who enters his third season, will help. A lot will be asked of Barnes, but a lot will also be asked of Ujiri, who is just beginning to scratch the surface of the work that awaits.

There have been challenging times for Ujiri in Toronto, but this year may emerge as the most challenging.

It has been four years since the Raptors won a playoff series and there’s no reason to believe this year will be any different.

Granted, the ball will move better in the Rajakovic offence, players will be asked to be more active off the ball, but under no circumstance will the Raptors, at least not as currently constituted, be among the top teams in the East.

Ujiri often swings for the fence and for that he must be commended. He’ll forever be known as the guy who helped bring an NBA championship to Toronto when he swung for the deepest levels in the upper deck to land Kawhi Leonard.

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Trades of that magnitude come around so infrequently that it’s virtually impossible to envision a similar franchise-changing deal.

Then again, if anyone is capable of engineering such a move, history is on Ujiri’s side.

He has assembled assets, but there’s no definitive go-to bucket-getter as the 2023-04 season gets underway.

Ujiri took a shot at acquiring Damian Lillard, but the electric wing and elite scorer ended up in Milwaukee to pair up with the Greek Freak, Giannis Antetokounmpo — an NBA champion in 2021 who has agreed to an extension with the Bucks that will see him under contract through the 2027 season.

When one begins to take a deep dive into the Raptors’ roster and the state of the Eastern Conference, one quickly begins to recognize the daunting task that lies ahead for Ujiri in making his team relevant once again.

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It speaks to the insecure nature of those covering basketball in the Toronto market when opinions based in the United States are given unnecessary oxygen.

One does not need to be an expert to realize the Raptors will not be making a deep run in the playoffs, if they’re able to even make the post-season. The goal in 2023 involves internal improvement and development.

Barnes, at least until proven wrong, has the highest ceiling.

As for Ujiri, he has to prove he can once again pull off that franchise-altering move. There will be no lack of trying, but so much will depend on circumstance.

“This is the team, now, that we want to take into next season,” Ujiri said when the Raptors gathered for their annual media day earlier this month.

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“Did we look at other opportunities (in the summer)? Yes we did. Did we look at maybe going younger? Yes we did. But sometimes those opportunities are there and sometimes they’re not there.

“I know everybody’s looking for trades, I know everybody’s looking for moves. Trust me — when the right ones come, the right opportunities come, maybe we’ll take those opportunities.”

In the history of the Raptors, there have been moments and opportunities when change was necessary.

One can go all the way back to the days when Vince Carter needed, for a lack of a better term, a bodyguard at the same time the Raptors needed toughness, when the NBA was played much differently than today’s perimeter-dominant era.

Marcus Camby, a young and emerging big, was dealt to the New York Knicks for Charles Oakley, who gave the Raptors instant credibility and a mean factor.

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Many years later, DeMar DeRozan would be sacrificed for Leonard.

Trades of this scope and consequence don’t come around often. Ujiri, like anyone remotely familiar with basketball, knows what is required to return the Raptors to title-worthy status.

Boldness is one thing, but timing supersedes everything.

Entering a new season, timing does not appear to be on Ujiri’s side, leaving one to wonder if his time in Toronto is about to run out.

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