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As the New York Knicks work through an NBA playoff series against the Cleveland Cavaliers, an intriguing offseason nonetheless awaits the team as it continues to search for an established superstar that would earn them entry into the Eastern Conference's penthouse currently led by Milwaukee, Boston, and Philadelphia.

Could that offseason include convincing Damian Lillard to finally sever his long-established loyalties to the Portland Trail Blazers? New odds hint toward the possibility.

Oddsmaker Adam Thompson has labeled the Knicks the top team to lure Lillard away from the Pacific Northwest in new numbers posted on Bookies.com. While the Blazers (+200) remain the top team for Lillard to spend the 2023-24 season, the best outside chances belong to the Knicks at +350, followed closely by their cross-borough rivals in Brooklyn (+450). 

Lillard's loyalty to the Blazers has been well-documented (spending all 12 of his NBA seasons there since entering as the sixth pick of the 2012 draft) but more questionable with the team's lack of recent success and long-term plan. Set to turn 33 in July, Lillard is regarded as one of the most accomplished players with an NBA title ring. Portland has missed each of the last two Western Conference tournaments and the Knicks were direct beneficiaries of their latest roster sale, gaining Josh Hart in exchange for Cam Reddish, Ryan Arcidiacono, Svi Mykhailiuk, and late draft considerations.

Despite dealing with Portland's meandering 33-win season, Lillard enjoyed one of the best years of his storied career: he averaged a personal-best 32.2 points and 4.8 rebounds and also took home top long distance honors at the NBA's 3-Point Contest during the All-Star break.  

The seven-time All-Star has repeatedly insisted that he's eager to stay in Portland for the long-haul but what New York has building could perhaps be too tempting to pass up.

As constructed, the Knicks are in a genuinely optimistic stage of their seemingly eternal rebuild. Headlined be the services of All-Star Julius Randle and newcomer point guard Jalen Brunson, the Knicks' ongoing playoff run is the result of a 47-win season and fifth-place finish, their best in a full 82-game slate since 2012-13. Brunson has proven to be well worth the four-year, $104 million deal bestowed to him last summer and the Knicks have further enjoyed contributions from Hart and Sixth Man of the Year candidate Immanuel Quickley. 

Further working in the Knicks' favor is the arrival of Hart, who spent parts of two seasons in Portland. Despite his relatively brief stay, Hart managed to leave a lasting impression on Lillard. 

"We actually formed a friendship and you just get used to people being around," Lillard said shortly after the February deal was agreed upon. Any time that happens it’s tough, but I think, for him, just knowing that he is a good dude, he’s a good person, I know that he liked being in Portland, he wanted to be in Portland and, you know, you get people to come here and know that they want to be here but the business takes over is just unfortunate."

"It’s part of the business. It’s the thing that I, I guess, struggle with the most about it, but it’s part of it and that’s what we signed up for."

Hart, partaking in his maiden playoff voyage, is widely projected to hit free agency this offseason by turning down a $12.9 million player option in his current contract. But the depth star has made little effort to hide his love of New York, hinting of potential for a metropolitan future.

While the Knicks would undoubtedly love to add Lillard to their fold, there are more immediate affairs to focus on: Madison Square Garden returns to the NBA playoff conversation on Friday night when the Knicks host Cleveland for Game 3 of their best-of-seven set (8:30 p.m. ET, MSG/ABC). 


Geoff Magliocchetti is on Twitter @GeoffJMags

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