Masai Ujiri is entering the most difficult season as the Raptors’ boss

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

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When a basketball conversation is initiated with the Raptors, it begins and ends with Masai Ujiri — the vice chairman and team president, better known as a risk-taker who has had his fair share of success and failure in reshaping the roster when changes were needed.

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

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

“Watching us play this year was not our job,” Ujiri said as he reflected on the 2022-23 season, which ended with a home loss to the Chicago Bulls in the play-in tournament. “I didn’t enjoy watching this team play. I think that spoke loud and clear about everything that was going on.

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“You could see it all year round. There has never been so much excitement. There was never that full spirit. There was never that sense of togetherness. We’ve all seen it. You’ve all seen it.

“We weren’t this year.”

Ujiri did what any manager would do, turning the page. To his credit, Ujiri has never been reluctant to effect change, be it behind the bench or on the pitch.

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

He’ll get a glimpse of the impact his new head coach will have starting Wednesday night when the Raptors begin their season against visiting Minnesota.

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Last season there was no joy in Raptorland, conceding a goal from Ujiri was too selfish.

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A more committed Scottie Barnes, entering his third season, will help with that. A lot is asked of Barnes, but also of Ujiri, who is just beginning to scratch the surface of the work ahead.

There have been challenging times for Ujiri in Toronto, but this year may prove to be the most challenging.

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

Granted, the ball will move better in Rajakovic’s offense, players will be asked to be more active off the ball, but under no circumstances will the Raptors, at least not with their current makeup, be among the top teams in the East.

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

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Transactions of this magnitude are so rare that it is virtually impossible to imagine a similar franchise change deal.

On the other hand, if anyone is capable of planning such a move, then history is on Ujiri’s side.

He has amassed some wealth, but there is no definite favorite heading into the 2023-04 season.

Ujiri tried to sign Damian Lillard, but the electric winger and elite scorer ended up in Milwaukee to team up with Greek freak Giannis Antetokounmpo – a 2021 NBA champion who agreed to an extension with the Bucks, who have him under Pressure will be placed on the contract until the 2027 season.

When you start to delve deeper into the Raptors’ roster and the state of the Eastern Conference, it quickly becomes clear what a daunting task Ujiri has to make his team relevant again.

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It highlights the insecurity of those covering basketball in the Toronto market when opinions held in the United States are unnecessarily oxygenated.

It doesn’t take an expert to realize that the Raptors won’t have much success in the playoffs, if they even make it to the postseason. The goal in 2023 includes internal improvement and development.

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

As for Ujiri, he needs to prove again that he can make this franchise-changing move. There will be no shortage of attempts, but a lot will depend on the circumstances.

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

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“Did we look at other options (in the summer)?” Yes, we did. Have we thought about maybe getting younger? Yes we have got that. But sometimes these options are there and sometimes they are not.

“I know everyone is looking for trades, I know everyone is looking for moves. Trust me – when the right ones come, the right opportunities come, maybe we’ll take advantage of those opportunities.”

There have been moments and occasions in the Raptors’ history when change has been necessary.

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

Marcus Camby, a young and up-and-coming player, was traded to the New York Knicks by Charles Oakley, giving the Raptors instant credibility and an average factor.

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Many years later, DeMar DeRozan was sacrificed for Leonard.

Trades of this size and consequence don’t happen often. Ujiri, like anyone who even knows anything about basketball, knows what it will take to make the Raptors title-worthy again.

Courage is one thing, but timing trumps everything.

As a new season begins, timing doesn’t seem to be on Ujiri’s side, making one wonder if his time in Toronto is soon running out.

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