This season, the New York Knicks have been one of the biggest storylines of the 2020-21 NBA regular season because of how much success they have had in head coach Tom Thibodeau’s first season in Madison Square Garden. 

Not only are the Knicks the 6-seed in the Eastern Conference with three games left on their schedule, but New York is one of the best overall basketball teams because of how good everybody on their roster has played. 

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Julius Randle has had a breakout, All-Star season and will most likely end up winning this year’s Most Improved Player Award, R.J. Barrett is continuing to grow into a star-like talent in his second season, Derrick Rose has looked like one of the best mid-season acquisitions and other key talents on this roster have stepped up in big moments, especially on the defensive-end of the court. 

Given how great they are defensively, the Knicks are going to be a tough team to beat in the playoffs this year, but as things stand right now, they seem to be missing that key, star-level player to be able to make them true contenders in the Eastern Conference. This is why NBA trade rumors have surfaced over the last few weeks about the Knicks potentially looking to go after Damian Lillard in the offseason. 

It would be a long-shot for the Knicks to even consider this move, especially since he is the face of the Portland Trail Blazers and loves his organization, but if Portland loses in the first-round of the playoffs or even in the play-in tournament, not only could there be a coaching change there, but they could look to switch things up roster wise. 

It is hard to believe that Damian Lillard would be the first player Portland would look to move in the offseason, but if the New York Knicks truly are “all-in” on the idea of trading for Lillard in the offseason, then this is likely one of the best trades they can offer the Trail Blazers for him. 

New York Knicks Receive: G Damian Lillard

Portland Trail Blazers Receive: G Immanuel Quickley, F Obi Toppin, NYK 2021 1st Round Pick, DAL 2021 1st Round Pick (via NYK), NYK 2022 1st Round Pick (Pick Swap, More Favorable to Portland), NYK 2023 1st Round Pick

Basically, this trade for Lillard includes a total of six first-round picks: Three unprotected first-rounders, one pick swap in 2022 and two first-round picks from this past year in Immanuel Quickley and Obi Toppin. Even with all of this value, the Blazers may still quickly decline this offer, especially since Damian Lillard is their franchise. 

While Obi Toppin was the eighth overall pick in the 2020 NBA Draft, it has been Immanuel Quickley that has been the standout rookie for the Knicks this season and while he is only averaging 19.6 minutes per game off-the-bench this season, he has been a key talent for them offensively all season long. 

To this point, Quickley has averaged 11.7 points, 2.2 rebounds, 2.1 assists and has shot 39.7% from three-point range. His abilities to create space and knock down shots from the perimeter is what has made him a unique rookie this year, but his abilities to draw fouls and get to the free-throw line is even greater. 

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He trails only Anthony Edwards for Free Throws Made and Free Throws Attempted by rookies this season and is third on the Knicks in both of these categories as well. Toppin has not played much for the Knicks, but given his length and potential to be a great two-way forward, he is absolutely a player that Portland would likely want in return, especially given their lack of youth in their frontcourt. 

This trade is definitely something to raise an eyebrow at and it contains a ton of value going to Portland, but who knows if Damian Lillard is even going to be available! With that said, let’s take a closer look at this trade from both team’s perspectives and truly see if this is something that could happen this offseason. 

Does this trade make sense for the New York Knicks?

It would be hard for the Knicks to turn down a chance of trading for Damian Lillard, but does this trade put them in a great position to succeed? Pairing Lillard with Julius Randle and R.J. Barrett gives the Knicks a powerful trio in the Eastern Conference and with about $27.5M in cap space after making this deal, New York could potentially add another superstar player in free agency. 

There have been a lot of NBA trade rumors that the Knicks have been linked to DeMar DeRozan for a while and with him coming from a defensive-minded system in San Antonio, he could fit in perfectly on the wing in New York!

While they would have to give up a ton of their future assets via draft picks and through both Quickley and Toppin, going after Damian Lillard gives the Knicks their best chance to succeed now and potentially contend for a championship. 

As crazy as it sounds given how bad they have been over the years, the New York Knicks are not far off from being true contenders in the Eastern Conference. All this team needs is that superstar talent like Damian Lillard to pair with Randle and Barrett in order to contend with the best of the best. 

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The whole point of having future assets is to try and build a team that can compete for a championship and with the Knicks having this chance to do so by leveraging these assets for Lillard, this trade definitely makes sense for them to do. Even if Portland wanted another first-round pick, I believe that the Knicks should do whatever it takes to land Damian Lillard in the offseason, as he can be the final piece to their championship puzzle. 

Does this trade make sense for the Portland Trail Blazers?

Unless Portland is giving up all hopes of everything, clearing house on everyone and entering into a rebuild, this trade makes absolutely no sense for them. The Blazers have made the playoffs for seven consecutive seasons, this year likely being the eighth consecutive year and while they have reached the Western Conference Finals just once over this span, they too are not far off from being something special. 

They have one of the best backcourt duos in the league with Lillard and McCollum, they have a two headed monster at the center position with Nurkic and Kanter and with some experienced veterans in Carmelo Anthony and Robert Covington, this team seems like that they are missing that one other piece that can push them over the edge. 

They traded for Norman Powell at the trade deadline hoping that he could be the third high-level threat from the wing, but the fit has not worked out the way this organization had hoped. Giving up on everything now seems illogical and foolish, which is why the Blazers should not trade Damian Lillard for all the draft picks in the world. Well… maybe if the Thunder offered up 10+ first-round draft picks for him but that is besides the point! 

The Trail Blazers have really nothing to gain from making this trade with the Knicks and if they were to either accept this trade or a similar one that New York offers in the offseason, they would be taking a major step back as an organization and have to go back to the drawing boards on how to try and build this team back into a contender. 

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Quite honestly, if the Blazers were to target a few key defensive players in the offseason that could help make them better defensively, then they could probably end up being a Top-4 team in the Western Conference. Offensively, they are as good as anyone in the league, but defensively, they are giving up points to anybody that plays them. 

Keep Damian Lillard; look to add more talent on the defensive-end of the court. These are the two things the Portland Trail Blazers should have on their “offseason checklist.”