A Damian Lillard trade could actually hamper Toronto for years

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The Toronto Raptors, like the rest of the NBA, saw their attention fixed squarely on the Pacific Northwest yesterday, as it appears as if Portland Trail Blazers guard Damian Lillard is trying to lay the groundwork for an exit. After playing almost a decade in Oregon, Lillard is reportedly too frustrated with the organization.

Lillard is citing the backlash from Portland’s frankly disgusting hire of Chauncey Billups as their next head coach despite the 1997 case in which a woman alleges he and teammate Ron Mercer performed unwanted sexual acts on her as one of the reasons he wants out, while also claiming that he doesn’t believe Portland can be a championship contender.

It sounds like the Raptors should do everything in their power to add Lillard, as adding a true superstar could be the ticket that helps them get back to the postseason. With his shooting, scoring, and clutch play all well beyond excellence, he would be one heck of a Kyle Lowry replacement.

Unfortunately, while Lillard would be an immense help in the short term, there is reason to believe that his financial situation could end up impacting the Raptors in such a negative way that they should hold off on trading for him.

Should the Toronto Raptors trade for Damian Lillard?

Over the last six years, Lillard has been named an All-Star four times while averaging 27.2 points, 4.4 rebounds, and 6.9 assists per game. He’s a superstar, and he’d be a perfect fit in Nick Nurse’s offense. As tempting as that fit looks,

Even if you swallow the fact that Toronto would have to part with players like Fred VanVleet and give up control of their draft for the next half-decade for Portland to even consider giving Lillard up, 2021-22 is going to be the first year of a four-year, $176 million supermax extension Lillard signed with the Blazers.

This contract will pay him in excess of $42 million in every season from 2022-23 to 2024-25.  With a cap hit of just under $50 million in his final year, Toronto may have to gut their roster in order to support such a hefty financial burden.

If one of the issues with Portland over the last few years was a lack of support around Lillard, would a Raptors team that will be forced to sell off some of their stars be any more dangerous? Could they keep both Lillard and Pascal Siakam and sign a bunch of veteran minimum guys? Would Siakam have to get kicked out.

Lillard is one of a select few players in the league that is so dominant and valuable that it actually might be a net negative to trade for him considering all of the weight that would have to be jettisoned to bring him on board.