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While they may have lost in the first-round of the playoffs this year, the 2021-22 season was a major success for the Chicago Bulls as an organization.

They eclipsed 40 wins and made the playoffs for the first-time since the 2016-17 season and they learned a lot about their core consisting of three All-Stars in DeMar DeRozan, Nikola Vucevic and Zach LaVine.

DeRozan is under contract through the 2023-24 season and Vucevic has one more year left on his contract, but LaVine is set to enter the offseason as an unrestricted free agent.

Early indications point towards the Bulls doing everything they can to keep their All-Star guard long-term, but he will not come cheap and Chicago is definitely going to have some competition.

Plenty of teams have already been mentioned as possible suitors for Zach LaVine in free agency and recently, ESPN's Brian Windhorst reported on his Hoop Collective podcast that there is not much certainty about LaVine staying in Chicago long-term.

Windhorst went on to mention that the Portland Trail Blazers have “popped up” as a potential landing spot for the two-time All-Star.

All season long, Zach LaVine has been asked about his future in Chicago and his upcoming contract situation, but he really has not given much clarity as to what he plans to do. Staying with the Bulls seems like the reasonable approach for him, but LaVine has said that he is excited to be an unrestricted free agent and will listen to every offer that comes his way.

“I plan to enjoy free agency,” LaVine told reporters following his team’s first-round playoff exit. “We're going to have to experience A through Z without making any fast decisions. I think that's something me and [agent Rich Paul] are going to go through and experience.

“You guys have been a really, really soft spot in my heart. I have to do this as a business decision, as a man, to not just be viewed one way and be like I'm automatically coming back or I'm automatically leaving.”

Based on his end-of-season comments, it seems like LaVine is truly  sitting on the fence about where his future in this league will be and in terms of going to Portland, they could certainly make a case for themselves to be an appealing destination for the All-Star shooting guard.

CJ McCollum is gone, making Zach LaVine the clear-cut No. 2 option next to Damian Lillard and the Trail Blazers have a lot to work with in terms of their young talents and roster reconstruction.

Anfernee Simons is a young guard on the rise in this league that Portland will very likely re-sign and he will be a favorite entering the 2022-23 season to win the league’s Most Improved Player award, Jusuf Nurkic could possibly return in free agency and Portland has multiple trade exceptions they could utilize to add more high-level talents around a core consisting of Lillard, Simons and LaVine.

Currently around $38 million under the tax line entering the offseason, Portland has multiple ways of opening up even more cap space and they could even leverage the contracts of Eric Bledsoe ($19.3 million) and Josh Hart ($12.9 million) to make room for Zach LaVine, while also keeping pieces like Anfernee Simons and Jusuf Nurkic.

This offseason, LaVine can earn as much as $212.3 million over five years from the Bulls and $157.4 million over four years from any other team in the league, according to Spotrac’s Keith Smith.

Chicago and Portland both find themselves in virtually the same place as opposite conference organizations and with others expected to show interest in Zach LaVine, the All-Star may very well be the most coveted free agent this summer. 

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