14 Winners and Losers of the Damian Lillard To Milwaukee Bucks Trade

I don’t love doing Winners and Losers articles because so many sports sites vomit them out but then I remembered my shit’s better so here it is.

Lillard goes Milwaukee as part of a 3-team deal with Jrue Holiday, Deandre Ayton, Toumani Camara, a 2029 unprotected MIL 1st, and unprotected MIL swap rights in 2028 and 2030 to Blazers. Phoenix lands Jusuf Nurkic, Grayson Allen, Nassir Little and Keon Johnson. https://t.co/Ge0H91AiIA

— Adrian Wojnarowski (@wojespn) September 27, 2023

Let’s start with the winners:

1. Giannis Antetokounmpo

In 10 professional NBA seasons, Giannis has never once played with an All-NBA teammate. And I know what you’re thinking. “What about Jared Dudley??” Nope, shockingly never made an All-NBA team.

Jrue Holiday is one of the best perimeter defenders in the league. Cool.

Damian Lillard is an exponentially better basketball player who averaged 32.2 points, 7.3 assists with a 64% true-shooting percentage.

We also don’t talk enough about Jrue’s atrocious shot selection. My man is a CHUCKER just bricking shots when he feels like it. I guess Dame does that too but, ya know, he usually makes those shots.

With Damian Lillard’s history of hitting big shots and a hopefully health Kris Middleton, the pressure is off Giannis’s shoulders. He doesn’t need another 50-point Game 7 performance.

In a Fresno barbershop called Phase II a few months ago, Giannis Antetokounmpo was asked of the one player he would like to play with. His response was Damian Lillard.

— Chris Haynes (@ChrisBHaynes) September 27, 2023

This seems important.

2. Tyler Herro

Tyler Herro’s name was getting dragged all summer.

The Heat believed he was a price and made it sound like they were making a massive sacrifice by including him in a Dame Lillard trade while the Blazers would have rather shut down the entire franchise than have Herro on their payroll.

Herro was posting corny ‘loyalty’ posts on social media. We get it.

Herro has a social life in Miami I’m sure he popped a bottle of champagne when the Woj tweet dropped and he learned he gets to keep doing blow with rappers he’d never be in a room with if he were drafted to any other team.

3. Deandre Ayton

Deandre Ayton could not hang with high-pressure Phoenix Suns games.

Whenever you listen to one of those podcasts hosted by NBA players and they talk about ‘guys who don’t love the game’, they’re talking about Deandre Ayton who plays basketball because he’s 7-feet tall and good at putting the ball in the basket and I’m sure he enjoys the direct deposits. But yea, Ayton isn’t the guy you want in your starting 5 when you’re going on a championship run. My man might use his PTO in the playoffs.

And now he gets to play on a rebuilding Blazers team with no sense of urgency. Time to coast. Get your 20 points, 10 rebounds, and your paycheck—don’t ever look up at the scoreboard.

4. Scoot Henderson

From everything I read, Scoot Henderson is a guy you give the keys to your franchise to. No point in playing around with an awkward on-court relationship between Dame and Scoot.

Give Scoot the rock and let’s watch him go from beloved ‘dog’ to a guy who leads the NBA in usage rate and becomes hated by the media.

5. Devin Booker and Kevin Durant

Kevin Durant is at the point of his career where he’s only going out there to win titles or he might as well retire. Devin Booker proved he can be the best player on an NBA Finals team. And now that BUM Deandre Ayton is gone and no longer terrorizing this ball club.

(Or they could end up on the loser list if/when Nurkic gets injured and Durant has to play center against Jokic and AD and the Suns are in a worse position than when they started.

6. Heat Culture

The mythology of Heat Culture©️ only exists if they are an underachieving team full of undrafted or underappreciated players who outwork their opponents. That ends when you add a 7-time All-Star and a guy who made the NBA Top 75.

Now when the Heat stink all season but sneak into the 8th seed via the play-in tournament, the Heat Culture scam can stay alive. Jimmy Butler, Nikola Jovic and vibes vs. Everyone.

And now onto the Losers…

1. Brook Lopez

Brook Lopez is 35 years old entering his 16th NBA season. And the best perimeter defender in the league is not only gone but he’s being replaced by Dame Lillard who might as well hang back on the offensive side and not even worry about getting back on D to let get swallowed up by every screen or just straight up crossed up by opposing guards.

Brook is about to get his legacy redefined when he’s on every poster getting dunked on left and right while Dame appears in the background looking back like he’s mad at the lack of help defense.

2. Jrue Holiday

“I don’t want to play for any other team. I think we have a chance to continue to do great things as the #Bucks team and organization so I want to be in Milwaukee.” – Jrue Holiday https://t.co/qNfDBRl3vu

— Jim Owczarski (@JimOwczarski) September 26, 2023

An article came out YESTERDAY where Jrue Holiday said there’s no team he’d rather play for than Milwaukee and the Bucks were cleaning out his locker while the article was being edited.

3. Mike Budenholzer

Coach Bud won a championship and was fired.

Now, the Bucks go into the 2023-24 with the most talented roster in franchise history and Bud has to sit at home watching his replacement, Adrian Griffin, win Coach of the Year and make a Finals run. Everyone is going to praise Griffin’s coaching while Mike Budenholzer gets erased from our collective memory.

4. New York Knicks

The New York Knicks were so fucking close to acquiring Giannis who said he wasn’t signing a contract extension with Milwaukee unless they were in a position to compete for titles andddd that dream is dead. Dame and Giannis are going to be at the top of the Eastern Conference for as long as they want.

(But keep an eye on Luka Doncic though).

5. Jusuf Nurkic

Jusuf Nurkic had the comfort of playing in Portland where he could kind of coast under the radar either resting on the sidelines nursing an injury or getting burned trying to defend the pick and roll.

Now he’s on a team with Kevin Durant—a guy who could sneeze during a game and there will be podcasts dedicated to interpreting the subtext and what it means for the Suns.

Nurkic is about to be exposed.

6. Pat Riley

Damian Lillard made it extremely clear he had only one destination in mind: Miami. Anddd look who isn’t in Miami.

There was a story saying Pat Riley made an initial offer Portland turned down but then Riley NEVER CALLED BACK FOR A SECOND OFFER. Now, I think that’s bullshit from the Miami side in an attempt to maintain Riley’s image as this Godfather who created the Art of the Deal even though his biggest free agent signing was LeBron a decade and a half ago and since then, outside of get Jimmy Butler, his biggest move was…uh…Kevin Love(?) Ew.

7. Suns fans

Phoenix Suns fans have to root for Grayson Allen. Yikes. Couldn’t be me.

8. CJ McCollum

Damian Lillard and CJ McCollum were the stars in Portland for nearly a decade. CJ McCollum was sent to go team up with the overweight porn addict while Dame was sent to team up with one of the greatest basketball players of this era.

And now CJ’s name is being thrown in trade talks again but in exchange to send Jrue back to New Orleans and bring CJ back to where it all started but in far worse shape than it was when he left.

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