Giannis Antetokounmpo Should Learn From Damian Lillard’s Situation

PORTLAND, OREGON – APRIL 02: Giannis Antetokounmpo #34 of the Milwaukee Bucks dribbles against Damian Lillard #0 of the Portland Trail Blazers in the third quarter at Moda Center on April 02, 2021 in Portland, Oregon. NOTE TO USER: User expressly acknowledges and agrees that, by downloading and or using this photograph, User is consenting to the terms and conditions of the Getty Images License Agreement. (Photo by Abbie Parr/Getty Images)

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The old adage, “the grass isn’t always greener on the other side,” could be a guiding principle for Giannis Antetokounmpo and the Milwaukee Bucks. It certainly proved true for Damian Lillard and the Portland Trail Blazers.

Drafted sixth overall in 2012, Lillard spent 11 seasons in Portland, delivering elite production and collecting an impressive list of accolades. From 2012 to 2023, he was one of the most dynamic point guards in the league—seven-time All-Star, seven-time All-NBA selection, and a member of the NBA’s 75th Anniversary Team.

On the court, he built a reputation as the most dangerous long-range shooter in the world not named Stephen Curry. He shot 37 percent from three for his career and consistently hit the toughest shots imaginable—contested step-backs, logo threes, and buzzer-beaters that defined playoff moments.

But all of that individual success couldn’t mask the team’s shortcomings. Over his tenure, the Trail Blazers reached the Western Conference Finals just once (2019) and advanced beyond the second round only two other times. They missed the playoffs entirely in his final two seasons, prompting Lillard to request a trade in the summer of 2023.

His preferred destination was Miami, but Milwaukee stunned the league by acquiring him.

The pairing of Lillard and Antetokounmpo promised to form the league’s most potent duo. Their complementary skill sets appeared tailor-made to cover each other’s weaknesses. And in many ways, Lillard delivered—earning All-Star honors in both of his seasons with the Bucks and averaging 24.6 points and seven assists per game.

He was a professional in every sense. He embraced his role, competed hard, and never publicly complained about playing somewhere other than his first choice. Yet, his heart remained in Portland. Being away from his family and adjusting to a new environment proved more challenging than expected.

His tenure in Milwaukee ended the same way it often had in Portland—early playoff exits. Even after battling back from a leg clot to return ahead of schedule, he suffered a torn Achilles in the postseason. The Bucks, facing a harsh reality, made the difficult decision to waive and stretch his contract this summer.

Now a free agent with Milwaukee still obligated to pay him the $113 million remaining on his deal, Lillard had the freedom to sign anywhere. He chose Portland, inking a three-year deal to return to a franchise that hasn’t made the playoffs since 2021 and is no closer to contending than when he left.

At his reintroduction press conference, his words carried the weight of hindsight: “It never felt right not being home” and “It all just feels right.” These are the reflections of someone who may regret ever leaving in the first place.

Antetokounmpo would be wise to take note. For yet another offseason, speculation swirls about his future. While there has been no indication he plans to leave Milwaukee, if that thought ever enters his mind, Lillard’s experience should be a cautionary tale.

Lillard left chasing a better chance to win. Instead, he found less happiness. Antetokounmpo has built his career, family, and identity in Milwaukee. As Lillard’s story illustrates, the grass isn’t always greener—and sometimes, the greener grass is the one you’ve been standing on all along.