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Grading the blockbuster Damian Lillard trade: Bucks become title favorites

Manolis Olandezos
Manolis Olandezos

Sir Charles in Charge

Damian Lillard (Rob Gray-USA TODAY Sports)

Damian Lillard is headed from the Portland Trail Blazers to the Milwaukee Bucks as part of a three-team trade also involving the Phoenix Suns. Here’s a recap of how each team will benefit.

Damian Lillard and NBA fans have been waiting since early July. It finally happened.

After months of speculation, the Portland Trail Blazers traded star point guard Damian Lillard. ESPN’s Adrian Wojnarowski reported on Wednesday afternoon that Lillard was heading to the Milwaukee Bucks in a three-team trade involving the Phoenix Suns.

Lillard had requested a trade from the Trail Blazers shortly after the NBA Draft. He hoped that Trail Blazers GM Joe Cronin would package the No. 3 overall pick in a trade for a veteran star. Instead, Cronin kept the pick and drafted G League Ignite guard Scoot Henderson. Lillard requested a trade at the beginning of free agency and will be playing alongside Giannis Antetokounmpo as a result.

Damian Lillard is traded to the Milwaukee Bucks

Lillard getting traded isn’t surprising. Lillard heading to Milwaukee is what sent shockwaves throughout the league and social media. The Miami Heat were rumored to be Lillard’s preferred destination earlier in the summer.

It was reported last week that Pat Riley and the Heat were daring the Blazers to find a better deal than their offer reportedly centered around Tyler Herro. The Toronto Raptors were rumored to be frontrunners to acquire Lillard earlier this week, despite Raptors president Masai Ujiri reportedly refusing to include forward Scottie Barnes in a trade.

Instead, Damian Lillard is headed to the “Cream City” and will join the Milwaukee Bucks. Many have already anointed the Bucks as THE championship favorites.

Did the trade make the Bucks THAT much better? How do the rosters of the Suns and Trail Blazers look after Wednesday’s blockbuster deal? Who won the trade? I decided to grade the trade from each of the three team’s perspectives.

My grades may surprise you…

Portland Trail Blazers
Portland Trail Blazers general manager Joe Cronin (Soobum Im-USA TODAY Sports)

Portland Trail Blazers trade grade: B

Heading to Portland: Jrue Holiday, Deandre Ayton, Toumani Camara, Milwaukee’s unprotected 2029 first-round draft pick, draft pick swaps in 2028 and 2030

This grade could be later bumped to an “A” if Portland gets even more out of this deal. I’ll explain.

Blazers General Manager Joe Cronin was put in a tough position when his star guard requested a trade out of Portland. He said all along that he would only make a trade involving Damian Lillard if it benefited the Portland Trail Blazers, even if it took months.

This was despite Lillard’s agent Aaron Goodman reportedly telling interesting teams that he would only play for the Miami Heat. This was despite Pat Riley allegedly daring Cronin to find a better deal than his. This was despite the Toronto Raptors making a late push to land Dame.

The Blazers got younger and more athletic at the center position by swapping the 29-year-old Jusuf Nurkic for the 25-year-old Deandre Ayton. Ayton is a double-double machine. Toumani Camara was a 2nd round pick of the Suns in this year’s draft and could be a solid frontcourt prospect.

The 2029 unprotected first-round pick that Cronin managed to get from Milwaukee could be valuable. The Milwaukee Bucks are built to win now. Both Lillard and Giannis could leave Milwaukee by 2029.

The Bucks would likely be a lottery team in that scenario. The Blazers could be a team on the rise in 2029 and will have an asset in that potential lottery pick. They could also move up in the draft if Milwaukee is in the lottery in 2028 and 2030 with the draft pick swap they agree to.

The most valuable player that the Blazers received in the deal is Jrue Holiday. The Trail Blazers are already rumored to be shopping the 33-year-old All-Star guard to a contender. Cronin could flip Holiday for a young star player, multiple young players, or a combination of players AND picks.

Cronin traded his franchise player to a contender while putting his team in a position to succeed. He is apparently trying to do right by moving Holiday to a contender. He kept his word and didn’t give in. Both fans and players alike will remember that.

For now.

Phoenix Suns duo (Photo by Christian Petersen/Getty Images)
Phoenix Suns duo (Photo by Christian Petersen/Getty Images)

Phoenix Suns trade grade: A

Heading to Phoenix: Jusuf Nurkic, Grayson Allen, Nassir Little, Keon Johnson

One of the question marks surrounding the Phoenix Suns after trading for Bradley Beal wasn’t regarding their offensive firepower. Kevin Durant, Devin Booker, and Beal are all among the NBA’s best shooters and scorers. The biggest question about the Suns’ roster was about their depth.

Not anymore.

Suns President of Basketball Operations and General Manager James Jones made the 2023-24 Phoenix Suns even better on Wednesday. He moved a former No. 1 overall pick in center Deandre Ayton. In return, Jones got an above-average starting center in Jusuf Nurkic, two solid rotation players in Grayson Allen and Nassir Little, and a young prospect in 21-year-old guard Keon Johnson.

Nurkic may not be as athletic as Ayton but may be a better fit for this Suns team. He brings a different skill set and isn’t afraid to mix it up in the paint. Allen is another shooter, brings toughness, and could be part of three-guard lineups for head coach Frank Vogel. Little could be an energy guy off the Suns bench.

Here’s the projected Suns roster after today:

  • Starters: Booker, Beal, Durant, Nurkic, Allen
  • Bench: Eric Gordon, Nassir Little, Josh Okogie, Damien Lee, Yuta Watanabe, Drew Eubanks, Bol Bol, Jordan Goodwin, Chimezie Metu, Ish Wainright

That’s not too shabby if you ask me. James Jones improved the Suns’ depth and made his team better today. He may have also solidified the Suns being the favorites to come out of the West this season.

Damian Lillard
Damian Lillard (Soobum Im-USA TODAY Sports)

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.

Manolis Olandezos

Manolis Olandezos

Manolis is based in Chicagoland and is a lifelong, but currently frustrated, Chicago Bulls fan. He has been a published blogger since 2021 through his work with The Sports Page Blog.