New Season, New Year: Big Things Lie Ahead for the Toronto Raptors

LAKE BUENA VISTA, FLORIDA - AUGUST 23: Toronto Raptors president Masai Ujiri (Photo by Kim Klement-Pool/Getty Images)
LAKE BUENA VISTA, FLORIDA - AUGUST 23: Toronto Raptors president Masai Ujiri (Photo by Kim Klement-Pool/Getty Images) /
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With the new NBA season and the dawn of a new year so closely aligned, let’s look ahead to what figures to be a seismic 2021 for the Toronto Raptors organization.

You could be forgiven for thinking that the Toronto Raptors just got boring. They sacrificed a lot to set themselves up for a free agent pursuit of Giannis Antetokounmpo next summer that never got off the ground. Now, they sit in a decidedly second-tier group of Eastern Conference playoff contenders with no obvious path — however hopeful it may have been — back to imminent contention.

But enough of the doom and gloom. The Toronto Raptors organization is simply too well-run to have one free agent disappointment derail the overall direction of the club. President Masai Ujiri and GM Bobby Webster haven’t stopped securing a core built on homegrown talent and possess no shortage of options moving forward, even as they navigate through a season in Tampa Bay that will likely result in an eighth straight playoff appearance.

It is those options that make the Raptors’ next steps so intriguing. While it appears that the club is set with a foundation of Pascal Siakam, Fred VanVleet, and OG Anunoby locked in for the long-term; team brass won’t sit idly by if they don’t believe that group has future title potential. So, where do they go from here? There are many moving parts within the organization and league-wide that could shape the Raps moving forward.

Masai Ujiri

To start, let’s focus on the biggest forthcoming domino for the franchise, one that won’t play a minute this season. Ujiri, of course, is the architect of not only the 2019 championship team but the golden age of the entire organization. His own pending free agency looms larger than any individual Raptor player.

A contract extension for Nick Nurse and an apparently forthcoming (???) new deal for Webster might prompt paranoid Raptor fans to wonder if Ujiri is laying the groundwork for his own departure. In truth, though, few know where his true motivations lie for the future. Does he even want to remain in basketball at this juncture of his career?

If he does, it’s hard to see a better fit than Toronto, where he has full autonomy over basketball decisions, a green light from ownership to dip into the tax to build a winner, and a promotional platform to further his philanthropic efforts (such as the annual Giants of Africa night).

The New York Knicks, who have long coveted Ujiri, offer a major market and a unique challenge, but also feature meddlesome owner James Dolan. Then again, who knows what the 2019 championship architect is thinking as he prepares for his own free agency.