What assets could the Toronto Raptors give up in a Damian Lillard trade?

The Toronto Raptors and Portland Trail Blazers have both seen their 2020-21 seasons end earlier than expected, as even the addition of Norman Powell couldn’t help Damian Lillard and Terry Stotts overcome a beat-up Denver Nuggets team. For the fourth time in five years, Lillard lost in the first round.

The reorganization in Portland is already underway, as head coach Terry Stotts has been shown the door. Lillard’s cryptic message on Instagram and pleas for the organization to hire Jason Kidd as their next head coach could be hinting that Portland needs to listen to his input and improve the infrastructure to keep him.

Naturally, this has reignited a firestorm of trade rumors, as his nine-year stint in Portland has seen him make just one Conference Finals appearance despite the good infrastructure around him. Masai Ujiri and the Raptors are trying everything to get back to contention, and trading for Lillard would certainly confirm that ambition.

However, Lillard is one of the few superstars in the league that is so good it actually could be detrimental to trade for him considering the deluge of assets that would need to be given up in order to acquire him. Still, gutting the roster for Lillard would help most teams improve their win-loss totals.

Do the Raptors have the assets needed to entice Portland in a hypothetical deal?

What could the Toronto Raptors give up for Damian Lillard?

Even though Lillard has proven to be a superior player, the Paul George trade might be a good barometer of what a swap might look like. In that move, the Los Angeles Clippers gave up a quality veteran in Danilo Gallinari, a young franchise player in Shai Gilgeous-Alexander, five first-round picks, and two first-round pick swaps.

In order to get a player of his caliber, it looks like one of either Pascal Siakam or Fred VanVleet would have to be moved. VanVleet, fresh off signing a four-year contract, could be more attractive for Portland by giving them a legit starting point guard without Lillard.

In order to both make the money match up and provide Portland with adequate value, the Raptors might need to part ways with Chris Boucher. Losing his presence in the paint will be a crushing loss, but Toronto would have to swallow that jagged pill if it means landing Lillard.

The Raptors own all of their first-round picks until 2025, but they would need to part with most or all of them to grab Lillard. 2021’s pick, which has the seventh-best odds at turning into the No. 1 pick, would likely have to be surrendered.

Due to the Stepien Rule preventing teams from trading first-round picks in consecutive seasons, giving up 2021 and 2023 while giving Portland the right to swap first-round picks in 2022 and 2024 gives the Blazers adequate value while also skirting around this provision.

A Lillard trade would completely turn the franchise upside down, but Masai Ujiri has a bit of a history with trading for disgruntled Western Conference stars, and there is a slim, albeit still slightly realistic, chance the front office pulls this off again with Lillard.