What the Damian Lillard trade means for Giannis’s future in Milwaukee

Who would have thought that Damian Lillard would be a Milwaukee Buck? From the outset, Lillard seemed to be destined to be playing with Jimmy Butler and the Miami Heat. Terrorizing the Bucks in the playoffs with ridiculous clutch shots over Jrue Holiday or any other Bucks defender. He made it clear that it was Miami or bust. Well, clearly that wasn’t the case as of 10 days ago according to Marc Spears, who reported that Lillard’s agent Aaron Goodwin privately told the Bucks and the Brooklyn Nets that the All-NBA point guard would be willing to play with those teams.

This trade completely changes the dynamic of this Bucks roster. As our own Mitchell Maurer put it, this puts the Bucks and Giannis Antetokounmpo in a whole “New Territory.” Giannis and Lillard have never played with a player that was close to the caliber player the two stars are. Lillard got close with LaMarcus Aldridge, but Aldridge left for the Spurs in Lillard’s fourth year in Portland. Meanwhile for Giannis, the closest he’s ever gotten to a player like that was Khris Middleton and Jrue Holiday. The idea of perhaps the second-best point guard in the NBA, with the range Lillard has from beyond the arc, and one of the most dominant interior players in the game in Giannis playing together is a match made in heaven for the Bucks offense. The pick-and-roll duo between Giannis and Lillard is going to be one of the best we have ever seen in league history. Not since the days of Kobe and Shaq have we seen a duo this dynamic. While teams had to respect Holiday’s shot in a pick-and-roll, it is going to be a nightmare trying to get over a screen from Antetokounmpo to contest a Lillard shot.

Outside of the on-the-court changes, this trade shakes up the future of the team's no. 1 star in Antetokounmpo. Prior to this massive trade by GM Jon Horst, the biggest story of the off-season was the fact that Giannis had stated that he would not sign an extension with the team this off-season, putting into question whether he would stay with the Bucks for the rest of his career. Now with another All-NBA level talent on this team, it seems Horst is making good on Giannis’ request that the front office stay committed to winning. The last time Horst traded for an All-Star guard, Antetokounmpo re-signed and the Bucks won the title, so maybe Horst is banking on that working again.

In all seriousness, Lillard’s contract itself seems to indicate that this partnership could last beyond Giannis' current deal, which has a player option for the 2025–26 season. Lillard has two years left, with a player option in 2026-27 at age 36 for $63.2 million. If the Greek Freak were to sign an extension before the Oct. 23 deadline, his player option year in 2025 would become guaranteed, with two more years on top of that. It wouldn’t make Giannis a free agent until 2028 at the age of 34, effectively carrying the two stars’ contracts together and potentially further if Lillard can keep playing at a high level. While it is still more likely that Giannis will not sign an extension by the 2023 deadline, it won’t be for roster reasons. If Giannis were to wait until next year to sign his extension in 2024, he could sign a deal worth up to three years at $193 million, earning himself $20 million more than an extension in 2023 would be.

Outside of Giannis himself, this will affect the rest of the Bucks core of players moving forward. As of now, every single player that will be part of this core (outside of Marjon) will either be expiring or have a player option for the 2025–26 season. Personally, I would expect Brook Lopez to either retire or take a pay cut from the two-year $48 million deal he got this past off-season. He will be 37 years old by the time his contract is up and with his injury history, I don’t expect Lopez to play at the level he did last year moving forward.

As for the rest of the guys, Middleton, Bobby Portis, and Pat Connaughton all have player options for that 2025 season. If Giannis were to extend to that 2028 marker, I would fully expect all three of those guys to be back either with the player option or with an extension themselves. Portis and Connaughton will just be turning 30 years old and will want one more big payday before they end their prime.

Middleton is a bit of a wild card, with his injuries the past couple of seasons and the fact that he’ll be 34 years old causing some concern. While that may be the case, Giannis clearly loves having Middleton around. According to old friend John Henson on Sirius XM NBA, the Bucks tried to ship out Khris Middleton for Jimmy Butler who was in Minnesota at the time and it was Giannis who vetoed the trade. It could get very tricky to improve the roster that currently still needs a backup point guard and more perimeter defense than it currently has. Shipping out Middleton for a package of players could be something we see down the line from the Bucks in order to keep the duo of Giannis and Lillard competitive. It’s hard to say exactly what will happen at this point, but how Horst keeps this team in a title window will be something that will give him a lot of sleepless nights in the near future.

This trade for Damian Lillard has not only made the Bucks the favorite out in the Eastern Conference, just ahead of Boston and Miami, but it has potentially secured Giannis becoming a Bucks lifer. We’ll have to see if the trade works out on the court and if the Bucks can live up to their championship aspirations. There will be questions about perimeter defense at the point of attack and how well head coach Adrian Griffin can integrate Lillard into this team. However, as for now though, this is a great move on the court. Despite the losses of Jrue Holiday, Grayson Allen, and picks that are for current high school and middle school-aged players, being able to hold on to one of the two best players in franchise history for his whole career, seems worth it to me.

I want to hear from you out there, what are your thoughts on how the Lillard trade affects Giannis’ future in Milwaukee?