28 Biggest Winners and Losers of 2023 NBA Free Agency

It looks like most of the big free agents have been signed and I’m not waiting for Grant Williams to make a decision so let’s see who won free agency and who lost.

Let’s start with the biggest winners:

1. Damian Lillard

Congrats to Damian Lillard for finally ending his abusive relationship with the Portland Trailblazers.

The two of them have been staying together despite very clearly being unhappy and falling out of love with one another but Damian Lillard declared he’d never get a divorce and Portland took advantage of that by never putting great players around him.

I don’t think Lillard will ever win a championship.

If you look at the history of the NBA, only the greatest players of all time lead their teams to rings. From Nikola Jokic to Kawhi Leonard to Steph Curry to LeBron James, if you’re not one of the greatest to ever dribble a basketball then you’re SOL.

Lillard and Jimmy Butler can certainly make a Finals run in the East and that’ll be the furthest Lillard has ever gotten which is a huge W for him.

2. Blazers Fans: Portland Trailblazers fans no longer have to pretend to think Dame is a good rapper. Thousands of people just updated their Spotify playlists and removed those Dame Dolla songs they always tried their hardest not to skip.

3. Dillon Brooks

Dillon Brooks went from being the best defender on a Top 5 NBA team to a dickhead who broke Gary Payton II’s elbow by tackling him in the air to a pest who motivated the Lakers to beat them to being told his organization was never bringing him back under any circumstance to stealing $80fuckingmillion from the Houston Rockets.

Now, he gets to walk onto a Rockets team as the ‘veteran leader’.

No one should give this man power and authority. He is absolutely going to abuse it.

Dillon Brooks thinks he’s Draymond Green so don’t be shocked when he knocks out Kevin Porter Jr first day or practice.

4. Fred VanVleet: FVV is the only free agent who signed a max contract this offseason. He’s my height and wasn’t drafted. Dwane Casey, Nick Nurse and Kawhi Leonard’s legendary 2019 run sculpted this guy into the player he is today. He also looks like a screenshot of a screenshot of a screenshot of a screenshot of a screenshot of Drake.

5. Milwaukee Bucks

I can’t say the Milwaukee Bucks improved in any meaningful way but there was a 36-hour window where I really thought this team was about to implode like that submarine but Khris Middleton and Brook Lopez re-signed and the Bucks are back.

Personally, I would have liked for them to make a big swing at a guy like Chris Paul or something.

Bringing the same exact team that lost in the first round might be a mistake but Giannis injured his back and perhaps Milwaukee will be right back in the Finals with a full season of health and uh, Malik Beasley now, I guess, who I believe plays better is cities like Milwaukee and Minnesota where there are only baddies sitting front row if the Pelicans are coming to town and Zion Williamson tricked all of his side chicks into flying in.

6. Indiana Pacers

The Pacers were stuck in no man’s land last season.

They weren’t good enough for the play-in and didn’t stink enough to tank for a top draft pick.

But they still found themselves in a position to improve by signing Bruce Brown and trading for Obi Toppin from New York.

Bruce Brown is the ultimate sixth man.

You know those moments when bench players are out there having no idea what to do in the half-court offense? Bruce Brown solves all that awkwardness with his ability to drive and dish. He almost forces ball movement with his own individual activity.

Obi Toppin gives them a new look in transition. Tyrese Haliburton has free alley-oop assists with Obi in the dunker’s spot now.

7. Obi Toppin: Obi was never going to succeed on the Knicks. He was drafted to a team with an All-NBA forward in front of him and played for the last coach in the NBA who still makes sure there is always a 7-foot center on the floor at all times.

8. Phoenix Suns

For a team with no salary cap space, the Phoenix Suns sure were able to sign a bunch of dudes including Eric Gordon, Damion Lee and Yuta Watanabe.

I could try to be a contrarian, shock jock who tries to drive up engagement by saying “What has Bradley Beal ever won??” or any of that nonsense but we all know Beal is good at basketball and he’s highly overqualified for his role on the Suns.

Look how great the Nuggets looked when they added Aaron Gordon—who was the man in Orlando but never really did much until he suddenly became way overqualified for his role. Bradley Beal has to hit open shots and try on defense. I think he’s capable.

Plus, this team still has a final big move in its back pocket if/when they pull the trigger and send DeAndre Ayton out of town. There could be a 4th star on this team by October.

9. Devin Booker: With Dame requesting a trade, Devin Booker gets to claim he is the last one left on the team that drafted him. He didn’t run from the grind. He just happened to be drafted to the dumbest owner who was caught saying the wildest racist and misogynistic garbage only for a brand new owner to come in and demand a fantasy basketball team.

10. Villanova Wildcats

At first, it looked like the Knicks were forming a Kentucky super team with Julius Randle, Immanuel Quickley and assistant coach, Kenny Payne.

Then it seemed like the team was pivoting into a Duke squad as RJ Barrett began to flourish and Zion Williamson was talking about how much he loves New York.

But nope, New York has gone all in on the 2017 Villanova Wildcats which is totally okay when two of those three shot 40% from 3 last season and the Knicks won 8 straight games after acquiring Josh Hart.

Just an incredible way to make everyone in that building know Jalen Brunson is the star of the team and you are all here as his support staff.

Now it’s time to acquire Mikal Bridges, the final Cat.

11. Russell Westbrook: I thought Westbrook would be out of the NBA by this time and he just signed a 2-year deal with the Los Angeles Clippers.

11. Victor Oladipo: Speaking of being out of the league, Victor Oladipo signed a deal with the OKC Thunder. In the last 5 seasons, Oladipo missed 272 out of a possible 410 basketball games. You’d think he’d run out of sick days but the Thunder are signing him to use up more paid days off.

12. Pat Bev: After signing a 1-year deal with the Sixers, Patrick Beverley definitely cannot wait for James Harden to be traded so he can step in and be the star of the team because, in Pat Bev’s mind, he IS James Harden.

13. New Wizards regime: New Team President, Michael Winger and GM, Will Dawkins, have an interesting little squad centered around Jordan Poole and Kyle Kuzma with plenty of assets to acquire a third guy. Wayyyy better offseason than the year they traded for Westbrook.

And now, onto the Losers…

1. Houston Rockets

I just want to show you a quick stat:

Dillon Brooks took 991 shots last year. He shot 39.6%. There is only one player in the entire NBA that took more shots and hit less. That player? Fred Van Vleet.

Not only that, Brooks shot 32.6% on 439 3pt attempts, the worst percentage in the entire league for that volume.

— Trashtalker – NBA discussions (@trashta59114252) July 5, 2023

The Houston Rockets crushed the draft.

Amen Thompson is the perfect backcourt partner with Jalen Green.

Cam Whitmore was supposed to be a Top 5 pick but fell to their lap at no. 20.

All they needed was some vets off the bench who know how to play basketball and don’t expect a ton of minutes.

Instead, they elected to give a bajillion dollars to Fred VanVleet and Dillon fucking Brooks—the 2 worst high-volume shooters in the NBA. They will not only be taking valuable minutes away from their young core but they will be ruining every offensive possession by jacking up bricks.

2. Jalen Green: Uh, um, a Jalen Green video leaked recently and uh, yea, that’s a freaky boy.

3. Sacramento Kings

Harrison Barnes signed a new 3-year $54 million contract.

Domantas Sabonis signed a new 5-year $217 million contract.

Alex Len and Trey Lyles are back.

Ok.

This team bought the Golden State Warriors to 7 games last season.

The Warriors acquired Chris Paul and the Kings brought back the same Harrison Barnes that missed that wide-open 3 at the end of Game 6.

Why is this team not only running it back but giving everyone bigger contracts?

4. De’Aaron Fox: De’Aaron Fox established himself as the most clutch player in the NBA. With 5 minutes left in a basketball game, Fox levels up to God mode and now after dragging this team to their first playoff appearance since the Bush Administration, he has to face the fact that they will never get past the first round because WHY IS HARRISON BARNES STILL HERE.

5. Cleveland Cavaliers

Last offseason must’ve been exciting as hell for Cavs fans.

Donovan Mitchell is the most talented player to wear a Cavs jersey since that guy who shared a link to Nazi propaganda. But this team still had their brains bashed in by the Knicks.

Their solution? Max Strus and Georges Niang.

Sick.

I know players aren’t rushing to sign in Cleveland but why isn’t Jarrett Allen traded yet? Why aren’t they moving on from Mitchell before he leaves in free agency next year? This team should have made a big splash. Scared money don’t make none.

6. Dallas Mavericks

We truly do not spend enough time talking about Mark Cuban being the worst owner in the NBA.

He had that gross-ass Sports Illustrated story where guys were leaving porn running on their computers and slapping girls asses. It was like what every 17-year-old Barstool Sports fan hopes their first job is like.

Then he hired a guy who got rich from gambling to help make roster decisions leading to a strange power dynamic between he and Cuban and the actual GM as well as with Luka who didn’t understand why Bill Simmons’s friend was suddenly his boss.

Former GM, Donnie Nelson, claims he was fired for reporting a sexual assault that occurred to his nephew by Mark Cuban’s assistant.

And then last season, the Mavericks traded all of their defense for the guy who I feel is 6 months away from telling us he invited a new Math.

Kyrie played 20 games in Dallas. The team went 8-12 and 5-11 when Luka played with him.

A 20-game sample size is enough to say these two don’t work together.

Oh and then there were those random rumors about the Mavs front office having a meeting midseason about trading for LeBron James but with his contract extension before the season, it was literally impossible for the Mavericks to make that trade, like, it was against NBA rules, so either the Mavericks had a serious meeting about trying to get a player they could not get or they planted that story in the media to show Luka they were doing everything they can to make his team better which is a lie.

This whole article could be about the Mavericks being massive losers.

At least they’re bringing in Dante Exum who was drafted no. 5 overall in 2014 and hasn’t played in the NBA in 3 years. The last time we saw Exum, he was getting into a brawl in Lithuania or wherever.

Real Madrid vs Partizan in Euroleague has been suspended after a mass brawl erupted between the two teams.

The fight started when Guerschon Yabusele body slammed Dante Exum.pic.twitter.com/eJhABjbmEu

— Sam Street (@samstreetwrites) April 27, 2023

The Dallas Mavericks are about to have the first pick next year. This whole franchise is poison.

7. Luka Doncic: I mean, did you read everything I just wrote? Free Luka.

8. Golden State Warriors

I’m okay with being wrong here but this felt like the time to move on from Draymond Green—not sign him to a new 4-year $100 million contract after a 9-point performance in an elimination game against the Lakers.

Bob Myers stepped away from the team and the first thing the new GM, Mike Dunleavy, did was trade for Chris Paul.

Again, I’m okay with being wrong if this team succeeds but I also get worried when a new GM tries to establish his legacy day one.

I don’t see Chris Paul playing more than 40 games this season and I see Jordan Poole going crazy in Washington.

Also, bold move to end the summer without acquiring a single player taller than 6-foot-9.

9. Chris Paul: A majority of Chris Paul’s failures have come at the hands of Steve Kerr, Steph Curry and the Warriors. At no point did he believe he was going to be their coworker and here he is on a press tour for his new book having to answer nonstop questions about being traded to Washington and Golden State.

10. Minnesota Timberwolves

Last offseason this team traded every asset they have for Rudy Gobert. They missed the playoffs. This offseason, their big move was signing Shake Milton. Ok.

I don’t have the energy to dunk on them because I’m still pissed at how the Mavericks are running their team like a dollar store where the cashier is the only employee working there so customers just walk in and steal whatever they want while she’s on her 15 minute smoke break.

It’s insane this team has Anthony Edwards sitting there ready to dominate this league and he’s handcuffed by the two most overrated big men of this era.

Why is Karl-Anthony Towns still on this team? Trade him for a second-round pick if you have to but it’s over. Build around Anthony Edwards. Yesterday.

11. Bradley Beal: For the first time in a long time, Bradley Beal faces pressure. He’ll play in nationally televised games alongside Kevin Durant—a guy people hate solely because he has a Twitter account. If he misses just ONE open jumper, Shaq and Charles Barkley are going to spend an hour roasting him.

12. Celtics writers: Every once in a while you are reminded how many NBA media members are from the city of Boston. It was nasty seeing so many people suddenly believe the Celtics were automatic champions after they got Kristaps fucking Porzingis—a player who’s proven how invaluable he is off-ball playing next to Luka Doncic yet will somehow flourish watching Jayson Tatum and Jaylen Brown iso back-and-forth. I’m glad they can no longer talk about the GREAT Marcus Smart.

13. Tobias Harris: Uh, the Harris family is not handling this offseason very well. Tobias’s dad said he was the greatest scorer on planet Earth and Tobias called anyone who disagreed a ‘casual’. Maybe this is why he seems to always go missing when the games matter most. He 1000% cannot handle his name being mentioned. Like, at all.

14. James Harden: Jimmy opted into the final year of his contract under the guise that GM Daryl Morey will work with him to find a suitable trade partner but we just saw Morey take his sweet time trading Ben Simmons. James Harden just got tricked into playing for the Sixers one more year thanks to a pinky promise across the table at Zahav.

15. Toronto Raptors: At some point, other teams are going to stop offering all of their future first-round picks for Scottie Barnes, OG Anunoby and Pascal Siakam. The Raptors could’ve really cashed out this summer knowing FVV was leaving but instead, they signed Dennis Schroder. Ok.

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