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NBA rumors: Raptors’ Damian Lillard pursuit was “aggressive”, huge offer made

By Mike Luciano

TORONTO, ON - JANUARY 22: Bobby Webster General Manager of the Toronto Raptors looks on before his team plays the New York Knicks at the Scotiabank Arena on January 22, 2023 in Toronto, Ontario, Canada. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Mark Blinch/Getty Images)
TORONTO, ON - JANUARY 22: Bobby Webster General Manager of the Toronto Raptors looks on before his team plays the New York Knicks at the Scotiabank Arena on January 22, 2023 in Toronto, Ontario, Canada. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and/or using this Photograph, user is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Mark Blinch/Getty Images) /
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The Toronto Raptors are back to square one as the preseason starts to inch closer. Bobby Webster and Masai Ujiri were reportedly trying to acquire Damian Lillard before the Milwaukee Bucks jumped in at the eleventh hour with a superior, Jrue Holiday-led package.

The question of how serious Toronto was in their pursuit of Lillard has been up for debate for some time. While Toronto was connected to him as frequently as anyone in the last few weeks, Ujiri and Webster were allegedly unwilling to part with OG Anunoby, Scottie Barnes, and Pascal Siakam.

The front office themselves seem to be hinting their Lillard pursuit was real, as they could take this (alleged) win-now team to the next level. Webster said Toronto’s offer for Lillard was as impressive as any past offer for a superstar player in franchise history.

According to Webster in a Media Day interview, the Raptors’ interest in Lillard was genuine, so much so that their “very aggressive” pursuit ended with them putting the largest offer they have ever made for an individual player on the table. Still, it wasn’t enough for Dame.

NBA rumors: Toronto Raptors were “very aggressive” in Damian Lillard talks.

The Raptors could have become an instant championship contender if Lillard was acquired, as he is still one of the best scorers in the game. With Lillard joining Giannis Antetokounmpo and Khris Middleton in Milwaukee, the Bucks are the favorites in the Eastern Conference.

If the three big names were off the table, it stands to reason that Gary Trent Jr. and many of the supplementary role players on the roster would have been funneled to Portland along with a treasure trove of first-round draft picks.

Instead of getting Lillard, the Raptors are left with three impending free agents in the starting lineup and just as many questions about the direction of the team as they had in the past. Lillard has also formed a superteam in Milwaukee, making their path to a championship even harder.

While we may never know for sure just how close Toronto was to getting Lillard, especially with Dame reportedly not putting the Raptors on his list of non-Miami destinations he would accept. If we are to take Webster at his word, Toronto gave it their all and couldn’t stand up to Miami’s offer.

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