You all know how the Kawhi Leonard saga played out — he came, he saw, he conquered, then he went home — but is it worth it for Toronto to make a similar play for Lillard?
Lillard is not Leonard. He doesn’t come with an NBA Finals MVP on his resume, or two top-3 regular-season MVP finishes, a couple of defensive player of the year wins or a reputation as a bonafide playoff killer.
But nor does he come with Leonard’s mercurial personality or injury history. And he’s pretty damn good, too, one of only 10 active players named to the NBA’s 75th anniversary team.
So, with a shout out to the late Bob Barker, we say it is worth the Raptors’ while to acquire Lillard — if the price is right.
For Mitchell, Cleveland surrendered three unprotected first-round picks, plus two pick swaps, plus a player who had just been taken 14th overall, plus future all-star Lauri Markkanen and Collin Sexton.
OKC got four unprotected firsts from the Clippers, plus two pick swaps and future superstar Shai Gilgeous-Alexander for George.
Minnesota, in an all-time screw-up, dealt four firsts, two swaps and five players, including centre Walker Kessler — third in rookie of the year voting last year and already arguably as impactful as Gobert — to Utah.
Toronto’s front office is not the type to offer anything close to those packages, but can still put more enticing deals on the table than Miami. Even with Scottie Barnes off the table, which he should be.
OG Anunoby is a premier two-way role player with designs on being seen as more than that. It probably can’t happen in Toronto, if Scottie Barnes or Pascal Siakam are around, but it can in Portland.
The Blazers have long coveted Anunoby, though he’s heading for unrestricted free agency and has little incentive to extend now when he can get much more by waiting until the summer.
If Portland gets the chance to talk to Anunoby about his intentions, he makes sense as a centrepiece of a deal, along with Gradey Dick — the 13th pick of the most recent draft — and something like a 2026 Raptors first-round pick (Toronto already owes a protected first to San Antonio in 2024, so can’t deal one then or in 2025), a 2027 pick-swap option for Portland and Precious Achiuwa or Christian Koloko, plus salary filler (Thaddeus Young, Otto Porter Jr.). That’s the type of deal that could satisfy both sides.
The financial argument against moving for Lillard is a valid one. Lillard is guaranteed $153 million over the next three seasons ($51 million per year) and then will surely opt in for a fourth year worth just over $63 million, the highest currently owed to any player of the 2026-76 season. Lillard also trails only Stephen Curry in terms of cap hit in 2025-26.
While Lillard’s annual cap hits won’t look quite as massive once other stars sign new deals and as the league’s salary cap rises, Lillard will be 35 and then 36 in the final two years of his deal. Father Time is undefeated and it’s quite possible Lillard no longer will be dominant in his mid-thirties. Plenty of stars have fallen off by that point of their careers.
Since missing only 25 games over his first seven seasons, Lillard has been far less durable. Other than playing most of the bubble year, Lillard has missed 16, 53 and 24 games.
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