By: Khaqan Khan

After years of touting his desire to avoid shortcuts and win the hard way by staying in Portland, Lillard is now coming to grips with his basketball mortality. Now 31 years old, Dame's time in his prime is slowly approaching its end. The window for this team, if there was ever one, to begin with, closed two years ago when they peaked by making the western conference finals in 2019. The roster as currently constructed does not have a lot of cap flexibility, and unless Anferee Simons shows something, no young pieces to entice other teams. Improving the team would mean trading CJ McCollum and Jusuf Nurkic, both of whom's trade value is at an all-time low. The next opportunity for Dame to leave is 2025 where he would be a 35-year-old unrestricted free agent.

Welcome back to Far-Fetched Friday, where every Friday we give you a bold prediction that we believe will come to fruition. This Friday, we look at Damian Lillard and the resurgent Knicks.

The Trail Blazers front office must be so grateful for Ben Simmons, Kyrie Irving, and Zion Williamson to take the 'disgruntled-star in a bad situation' light away from Damian Lillard. After a rocky offseason, where Lillard wasn't shy about not liking his team's current chances, the Blazers responded by resigning Norman Powell for $90 million, signing Cody Zeller, and trading for Larry Nance. To make matters worse, Lillard got heat for the controversial hiring of Chauncey Billups. Over the summer, Lillard seemed to test the waters by having reports come out that he might ask for trade only to later backtrack by complimenting the fans. All of which seemed like groundwork to soften the blow when the inevitable happens.

Here come the Knicks with young pieces, cap space, and a winning structure.

Under World Wide Wes, The Knicks haven't been shy about their desire to have a star point guard. They have been in every discussion about potentially acquiring a point guard. Fred Van Vleet, signing Chris Paul, or even trading to Russell Westbrook. They were smart enough to be patient and by their time with a hometown hero in Kemba Walker.

Along with cap filler and draft capital, they could trade three of their four young players in RJ Barrett, Immanuel Quickly, Obi Toppin, or Mitchell Robinson to pair Lillard with Julius Randle. They would still have players like Nerlens Noel, Derrick Rose, and Evan Fournier to piece together another trade for a high-end wing. Not to mention, with Dame in New York, the Knicks can lure almost any free agent they want without having to overpay them. We would have to wait and see if James Dolan is willing to pay the luxury tax to have a legit chance, but nonetheless, the Knicks have room to maneuver.

Could you imagine how loud Madison Square Garden would be when Dame hits a shot from the logo late in the game in the Playoffs? Playing alongside Randle on a defense-first team would take a lot of pressure off Dame. The team would make up for his defensive inefficiencies and would mean he wouldn't have to go nuclear every night to keep his team in the game.

Everything about Damian Lillard as a basketball player suggests he strives for glory. Other players pursue championships to seek validation, while Lillard opts to stay in a small market for an above-average team for the sake of respect. However, it's hard to attain glory in sports when you're not winning. That's what has been bothering Lillard all off-season and will continue to do so if the Blazers stay on their current track. Damian Lillard could stay on Portland so he can say he stayed even though deep down he knows that team will never win, or he can view it as he's earned the right to ask for a trade. Ultimately, Lillard has to understand that outside of Portland, basketball fans won't hold it against him for leaving. Even in Portland, he's solidified himself as The Portland Trail Blazer.

It's nice to have a superstar like Dame in a small market team, but it's even better for the league to have Dame in a place like New York playing in Madison Square Garden in front of the most passionate fans in the league. At the end of the day, Lillard will decide what's best for him, and it seems like he's already made his mind up, but not without guilt. To Lillard's credit, he wants to do this the right way, which is why I think he'll wait till the off-season. 

When Lillard does decide to request out, the first team that will call is the New York Knicks.