Other teams reportedly convinced Toronto serious about Lillard trade

Portland is talking to everyone but Miami about a Damian Lillard trade and one team has emerged as a serious suitor — the Toronto Raptors.

NBC Sports has reported on that buzz, and now the well-connected Marc Stein is the latest to discuss Toronto as a possible Lillard destination in his latest newsletter, and he adds the caveat everyone has with this trade.

The Toronto Raptors have convinced numerous teams around the league that their interest in trading for Lillard is genuine. The uncertainty at this point stems more from gauging Toronto’s true willingness to push all the way forward with its Lillard pursuit when it’s believed that the All-Star guard, behind the scenes, remains so resistant to the idea of becoming a Raptor.

There are a few things that could trip up this trade up, and the most obvious one is that Lillard would not drop his trade request. He would show up to Toronto and play, but the request would still be there, the pressure on the Raptors to deal with it would still be there, and the constant discussion about it — team president Masai Ujiri, coach Darko Rajaković and the Raptors players would be asked about it constantly — could become a huge distraction.

Another question about this trade involves who would be part of the trade from Toronto’s end. The name most commonly used is OG Anunoby, a coveted wing player, but also one who can be a free agent after this season (he has a $19.9 million player option he is expected to turn down because his market value is higher than that). Portland likely would prefer Scottie Barnes, who is four years younger, has two seasons left on his rookie deal, and is seen by some as having a higher ceiling. Toronto has been unwilling to put Barnes in any trade to this point. Beyond just who would be part of it, this likely would be a multi-team trade and could involve Deandre Ayton going to Portland and Jusuf Nurkic heading to Phoenix, and bigger deals are exponentially harder to put together.

Masai Ujiri and the Raptors front office tend to be cautious (some of the team’s fans would say too cautious). They didn’t trade Kyle Lowry and he bolted to Miami (in a sign-and-trade but all Toronto got back was an older Goran Dragić and Precious Achiuwa). They didn’t trade Fred VanVleet and he signed with Houston this summer. Is a cautious team like the Raptors going to bring in Lillard, knowing he wants to leave but believing they can win him over?

This much we know: Toronto is in talks with Portland and the rest of the league thinks they are serious, but nobody is entirely sure. Still, momentum is building and it feels like a Lillard trade will get done before the Oct. 2 media days for both teams. The only question is where Lillard is headed.