Grading the blockbuster Damian Lillard trade: Bucks become title favorites

Milwaukee Bucks trade grade: A-

Heading to Milwaukee: Damian Lillard

The Milwaukee Bucks were Eastern Conference contenders before this trade. They are the obvious frontrunners to come out of the East this season now that they have added Damian Lillard.

I also believe they heard Giannis Antetokounmpo’s comments about wanting to play for a contender loud and clear.

Dame joins the “Greek Freak” in Milwaukee to form a lethal scoring 1-2 punch. Don’t forget three-time All-Star and perennial 20-point-per-game scorer Khris Middleton. Good luck to opposing teams trying to stop all three of those guys on a nightly basis.

The Bucks gained a player named to the NBA’s 75th-anniversary team coming off his best scoring season. Lillard has unlimited range, is a willing passer, and is unafraid of the big moment. Lillard will also help the Bucks stretch the floor and open opportunities for Giannis inside.

He’s also a significant upgrade at the point guard position from an offensive standpoint over Jrue Holiday.  Who would you rather have on your team: Damian Lillard or Jrue Holiday? Most, including me, would say Lillard.

It helps that Bucks GM Jon Horst didn’t have to give up Middleton or significant roster depth to acquire Lillard. How’s this for a potential starting five for the Bucks?

Giannis Antetokounmpo, Damian Lillard, Khris Middleton, Brook Lopez, Malik Beasley or Pat Connaughton.

Hell, they could trot out Bango the Buck and still have a potent starting five! So why didn’t I the Bucks an “A+” for this trade? Honestly, I almost gave them a “B+.”

There isn’t a lot NOT to like for the Bucks with this trade. It does come with risk. The first is Damian Lillard’s health. When Dame is on the court, he’s still one of the best in the NBA. Lillard has missed significant time the past two seasons due to injury. The Bucks need a healthy Lillard to compete for an NBA title.

While the Bucks gain a prolific scorer in Lillard, they do lose one of the league’s best defenders in Holiday. Who covers the opposition’s best perimeter player now? Sure, no one really plays defense in the NBA anymore. Come playoff time they do. That’s when I think the Bucks could miss Holiday more than most people think.

There is also Dame’s contract. He has four years and $216.2 million left. Lillard will be 36 years old heading into that final season which would potentially pay him $63.2 million. I’ll spare you the salary cap tax penalties and potential financial ramifications. They’re scary.

The Bucks didn’t give up a lot today, but they may have given up a haul for tomorrow. Milwaukee sent its 2029 first-round draft pick to Portland as part of the trade. They also gave Portland the right to swap first-round picks in 2028 and 2029. Why does that matter?

Lillard will be 39 and Giannis will be 35 in 2029. My guess is that neither will be in Milwaukee by then. The Bucks will likely be rebuilding, perhaps without high lottery picks for three years.

Of course, none of that matters if the Bucks win the championship this season and/or next. The chances of Giannis signing an extension to stay in Milwaukee look much better after today.

Jon Horst needed to make a gutsy trade and he did it. He may have kept his franchise player from leaving town as a result. Regardless, it’s now “Dame Time” in Milwaukee.