A highlight from A Dame Trade Deep Dive With Ben Thompson, Plus Seth Meyers and Million-Dollar Picks


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We did the big chill. It was very, very exciting. I have Kyle Brandt coming on Monday's podcast. I'm just gonna tell you the movie now because it is gonna be the best moment of your weekend if you spent two hours watching this classic. We're doing Toy Soldiers. It really brings everything possible to the table. So if you wanna watch it ahead of time, there it is. That podcast is going up Monday night. If you wanna hear stuff about the debate, we have Tara Paul and Mary's podcast, Somebody's Gotta Win. That reacted to it as well as the press box with Brian Curtis and David Shoemaker. So there you go. Our debate coverage has been on point. Also, higher learning. Van and Rachel had Larry Elder on this weekend. It made a lot of noise, man. That podcast is great. I hope you check that out as well. Hope you're checking out theringer .com. And on this podcast, gonna talk about the dame trade at the top. We're gonna bring in Ben Thompson from the Techery newsletter, which he's been on this podcast I think four weeks ago. And he's a huge Bucks fan. He's gonna give the Bucks fan side of things. We're gonna do million dollar picks. And then old friend Seth Meyers talking about a whole bunch of stuff. So really good podcast. It's all next. First, our friends from Pro Jam. What's up? All right, I'm taping this on Thursday afternoon. Normally when there's a big MBA trade, I always do the emergency trade reaction right after the podcast. But we just put up a podcast on Tuesday. So I decided to play it a little differently this time. I wanted a little distance, I wanted to listen to stuff, read stuff, and try to form some big picture opinions coming out of this. So I have four smaller ones, then one big one. First one, I thought Portland did an incredible job with this trade. I really liked this trade, especially everyone was trying to bully them in June and July about, oh, you got to take Miami's offer. You just got to. It's where he wants to go. It's the only offer you're going to get. And guess what? They waited. They played it perfectly. They stared Miami down, and they got a much better deal. First of all, they get the Drew Holiday piece that they can flip into a bunch out of their stuff, which we'll talk about in one second. I love the DeAndre Ayton gamble. As you know, on this podcast, I am a big DeAndre Ayton guy. Not in the sense of I'm the biggest fan of his in the world, but I'm a fan of the asset. I just think I love the valued assets, no matter what it is. Whatever market we're talking about, DeAndre Ayton, 18 and 10 for his career, 60 % field goals percentage, 25 years old. He's played in 45 playoff games. He played four rounds in the 2021 finals. Last year, he got his ass kicked by Jokic. Oh, sorry. Like, that never happens. And Phoenix just sold on him, which I can't wait to talk about. But just from a Portland standpoint, they not only get Ayton in whatever they get for holiday, they get the 29 first, they get the two swaps, and they dump Nurkic. Nurkic hasn't had a healthy start to finish all the way through the playoffs here since 2018, which I'm positive was a long time ago. He's basically 12 and 8. He's, you know, a 50 % shooter. I made a list of the top 30 centers. I encourage you to do this at home, because what's more fun than making lists of NBA centers? I can't imagine anything. I made a list of who I thought were the best assets of the center position for talent, contract, everything. He was 29th on my list. The only person I had ahead of him who's technically a starter, unless you start talking about the Detroit or Charlotte guys, was Zubats on the Clippers. I thought he was the 29th best center asset in the league. And Phoenix, you know, just quickly to go to them, they're trying to win this year. They got worse. They turned Ayton's money into Nurkic and Grayson Allen and Nasir Little. Grayson Allen, we already know with him, he can't play in playoff series. We saw him 22. We saw it last year. I heard and read in some places like that, I got two rotation players. Did they? Is Nurkic a playoff rotation player? Is Grayson Allen a playoff rotation player? Because I'm positive he's not. So for the same money that they were spending on Ayton, they got three guys that I don't think are going to help them. In 25, the money comes down a little bit to 23 million just for Nurkic and Little, which is 7 million less than Ayton. And then in 26, that money goes up to 25 .5. But I don't understand what Phoenix was doing. Why not wait to see if Ayton clicks with Vogel? Vogel has such a good history with centers. He rejuvenated Dwight Howard on the 2020 Lakers. He basically created Roy Hibbert's career in 2013 with the defense verticality thing. I thought he was going to do a good job with Ayton. I'm stunned that they gave up on him. I'm almost waiting for one of those, now they tell us stories when, you know, that's where Brian Curtis calls them, where like a week after something happens, there's this kind of notebook dump where it's like, here's seven terrible DeAndre Ayton stories. So maybe that'll happen. But for Phoenix just to be like, cool, we locked this down, man. We got Nurkic. You're trying to win the title. You have KD and Booker and Beal. And like, what are you guys doing? Anyway, from Portland's standpoint, I love the Ayton thing. I love that they didn't get bullied. And I know they're going to turn Drew Holliday into something. So this to me was at least an A minus for them, for where they were two months ago, where Dave's like, I want to go to Miami. That's it. And if you don't trade me there, that's kind of fucked up. And they made this work as it got reported that, uh, I think in the athletic, that he expanded his list to Brooklyn and to Milwaukee in the last two weeks. And that's what Portland was waiting on. You know, they were banking on the fact that he's a competitive dude. He's one of the best 75 pairs ever. He wanted a situation settled. So, you know, you wait, you wait, you wait, they expand the list and then you go. Uh, there's a Drew Holliday piece to this. That's awesome. He becomes a contender prize. I wouldn't call this a Drew Holliday sweepstakes. I reserved sweepstakes for the superstars, but it's a mini sweepstakes. This is somebody that could have a huge impact on the playoff race. You know, not only the usual suspects, everybody's talking about Boston, ironically, Miami is a really good fit for him. And in some ways, um, I'm a little more scared of them with Miami than Dame in some ways, especially at a much cheaper contract with giving up less and keeping some of their assets. Philly, if they could pull it off, they have to be in there in Golden State, Minnesota. I think I have to mention Sacramento, I think is a team that if they could figure out how to get Drew without giving up their core, which is basically Keegan Murray and Sabonis and Fox, like that's, you know, could Davion Mitchell be in that trade with some, with a salary and some picks, who knows. The team that I love for Drew Holliday is OKC. I have OKC, you know, I started doing my MBA research for the over -under spot and I haven't landed on a number for them yet, but to me, they feel like a high forties team with Chet and with the growth of their young guys. And if you just like, let's say they traded Lou Dort and a bunch of their picks, maybe two firsts and two of their lesser picks or three firsts and a second, whatever it is. And they just say, fuck it. And they get Drew and you put him with Giddy and SGA and Jalen fucking awesome Williams and Chet Holmgren and all these other dudes they have, that might be a top three team in the West. I mean, that, that's starting to give me some early 2010s OKC vibes. So where he goes is going to be important. I just feel like there was so much Drew Holliday slander the last couple of days. You know, he's one of my favorite players. Even Haralabob, who was the chairman of the board of the Drew Holliday fan club for years and would have the benefit dinners there and, you know, just did a lot of yeoman's work on that front. And even he was like, yeah, yeah, Dame's better than Drew. That trade makes sense for Milwaukee. I was hurt, Haralabob. I was 100 % hurt by that. But you know, Drew got his ass kicked by Jimmy Butler in the playoffs last year. I get it. It happens. Jimmy was unbelievable. I feel like he would have kicked anybody's ass. By the way, why is Drew Holliday guarding Jimmy Butler? That speaks more to some of the issues with Milwaukee. He was never supposed to be a point guard and a creator. I think he was always better as an off -the -ball guy. We saw that with Rondo and New Orleans and just in general. I want to see him with a point guard. I want to see him just being unleashed, not having the ball a lot, just worrying about hitting threes, being an occasional, you know, make -shit -happen guy and being like the third or fourth best guy on a team without having the offensive responsibility to have. All their half court issues got blamed on him for the last couple of years. And I get it. They weren't like an awesome half -court team, even the other one in the finals, but I really value that dude. I had him, even I did the trade value list in August and I had him 37th and I had Dame 23rd. I think he's one of the best 30 players in the league still. He's 33 years old, which, you know, I'm going to talk in a second about when guards hit their mid -30s, but just in general, I think he's a real asset. If he goes to a team like the Celtics and they can keep Derek White and Tatum and Brown in the center, it's like, look out, man. So little mini sweepstakes, rarely do we get the trade, but then we still get another asset to talk about. Thank you for everyone involved in the trade. And then the fourth small point is just that, you know, not rocket science, Milwaukee bought some Giannis time here. They have one of the best 20 players of all time. They were staring down the barrel of a situation that was not good. I was talking about it on this podcast in late June and early July. I thought he was going to put them on the clock. I thought Mark Lasry selling his stake was a really bad sign for all of this because that dude is smart. As I laid out in June, that guy is really smart. And if he's feeling like, you know what, it's time for me to sell my buck stock, that makes me nervous. And then all the stuff that Giannis said and did, which I thought he did really fairly and really smartly. And I think that dude's about titles and that's it. And I know we say that about players, but I think in his case, I don't think he cares about, you know, what's my legacy, how do I compare against Dirk DeWhisky, any of that stuff. I just think he wants more rings. I mean, think about the guys who have won two rings out of the best 35 guys on my list of my pyramid. Those are all guys in my top 35 that won multiple wings. You go to the one -ring side, Jerry West, Oscar, Moses, Dirk, Jokic, Giannis, Pettit, Garnett, Kawhi, Rick Barry. That's the list he's on now. I certainly don't think he's looking at that list going, I got to get away from these guys, but it's a slightly different list. I think when you win multiple rings in multiple situations, it elevates you in a certain way. I think he fundamentally understands that at least a little bit. I want to be the best player since LeBron James. I think that's a thing that he wants. How am I going to do that? I need more rings. I need more finals trips. He knew from last year and maybe even the Boston series that they just weren't good enough. Whether this trade is going to be the thing that propels them, we'll find out, but he's been in the league 10 years, two MVPs, five first teams, two second teams, and now we have this little two -year window. Kawhi and the Raptors was a one -year window. This is a two -year window, I feel like. With Giannis, he's got two years left in his deals. So does Lopez. Middleton has two in a player option. Dame's got two, and then this crazy $120 million player option extension thingy that he has that just keeps going and going. It's probably two years. There's a world where this could go terribly this season, at least for what the expectations are, and then maybe it becomes Kawhi, Raptors. Maybe Giannis is like, you know what? That didn't work. Trade me. And the Bucks, who have no picks left and no future, they look at it next summer, and they go, all right. We tried it. Giannis, what can we get for you? Dame, what can we get? And they just do a reboot, rehaul. Remember, they won in 2021, which just takes so much pressure out of this. It's so much different than the Clippers situation, where they went all in on Kawhi and Paul George. They give up all those picks and SGA, and they've gotten nothing out of it. They haven't even made the finals. So it's got to happen. I think they at least probably have to make the finals. If they get bounced in round two, do I think Giannis is going to stay because they made this Dame -Mower trade? Probably not. So that leads to the big question, is how good of a trade was this? So there's a big picture angle on Dame, and it's going to sound negative, but I really don't want it to sound negative because I think Dame, I voted for him for NBA Top 75. I think he's been one of the best guards in the last 15 years. I think there's a ton of great things you can say, and there's a chance that he goes to Milwaukee, and this thing is fucking awesome. I know any Celtic fan I've talked to, including Isaiah, who's helping produce this podcast today, the Giannis -Dame pick and roll is just terrifying. Other than Jokic and Murray, it's going to be the single most unstoppable offensive play in the league. It is. We are conceding that point. The spot Dame is in right now, big picture -wise, it's weird. He's a superstar, but he's not, and we've seen guys like this before. I judge superstars by, do you have the resume statistically, and is your team succeeding consistently at a certain level? You can't totally say that about Dame. He's never been on a 55 -win team. He's missed the playoffs completely four times in 11 years. He said three first -round exits. He made the Final Four once in 2019, which was really lucky because Golden State and Houston were the two best teams, and then they got smoked. He's never been on a true contender ever. Instinctively, you go, well, that's not his fault. Who's he played with? Well, he played with LaMarcus Aldridge and CJ McCollum and a couple other guys, but not really anybody. The reason I'm putting this up is there's a success element that he has not had yet that for somebody with his resume is actually kind of unusual. I went and I looked up how many guards in the history of the league averaged 22 points a game for their career and played at least 700 games. I thought the list would be like 20. I didn't know. I didn't know what I was walking into. Only I think 75 guys have averaged 22 a game. So I went and I looked up the list, and it was 10 guys, 700 games, 22 a game for their career. There were some guys who came close like David Thompson, who I think is one of the best guards I've seen in the last 45 years, but had a short career and had some drug issues. He didn't make it. He didn't play enough games. Pete Maravich, 24 .2 points a game, but he didn't play enough games. Kyrie hasn't played enough games yet. Bradley Beale is five games away. I'm actually kind of glad the cutoff's at 700 so we don't have to talk about him. And then Mitchell and Trey Young aren't there yet. There's only 10 guys that made it, and the 10 guys are all fucking awesome. And again, I mentioned this in the context of Dame, who we think he is versus the success he's had. So the 10 guys, Michael Jordan, 30 .1, Jerry West, 27 .1, Allen Averson, 26 .7, George Gervin, 26 .2, Oscar Robertson, 25 .7, Kobe, 25 .0, Harden, 24 .7, Curry, 24 .6, Wade, 22, barely made it, and Russ, 22 .4, and then Dame is at 25 again. All right, what does he not have that those other guys have? Well, MJ, don't need to talk about him. Don't need to talk about Jerry West, who's the freaking logo. Allen Averson, pretty good comparison, right? Big stats, really memorable player, but not a ton of success. Here's the difference. Averson made the finals once. He won an MVP. Dame has done neither of those things. George Gervin was the best scoring guard of the 70s. He made two final fours. He had some bad luck. He really, in 79, really should have came close. And some of it's on him, right? He could have come through. Bobby Dandridge is the one that ended up coming through for the Bullets. They lose. But two final fours, he had four top five MVP finishes, five first teams, four second teams. He was just unassailably the best guard in the league until MJ. Oscar Robertson, don't need to go through him, but he won a ring and an MVP. Kobe, five rings and an MVP. Eleven first teams for Kobe, by the way. James Harden, three final fours, an MVP, six top five MVP finishes, six first team MBAs. And even though Harden has never made the finals as the best guy, he made it with OKC as the sixth man, you could build a contender around Harden. We saw it. We haven't really seen it with Dame. I think that's a fair thing to bring up. Curry, four rings, two MVPs, you know, the Curry thing. Dwayne Wade, three rings, two top five MVPs, two first teams, three second teams. He's more in the Dame waters a little bit, but he had the 2006 finals and he was the second best guy with LeBron on those heat teams. And then Westbrook, who you would say, well, Dame had a better career than Westbrook. Did he? Westbrook made the finals in 2012. He was second best guy on that team. Almost made the finals in 2016. He won an MVP. He had two first teams and five second teams. It's at least like a real argument. And I think when you look at Dame, he only had that one 2019 round three, got bounced. He's only had one top five MVP finish. He's only had one first team MBA and four second team MBAs. Really, really good top 75 career. But the piece that's missing is, have you been on a really good team? Have you made a real run at it? Which is why, you know, I think this Milwaukee trade is so much fun. This is his real chance. I get nervous about a couple things with this trade. One is that, you know, if you look at the 33 and older guards who average 22 points a game in a season. Jordan did it twice. Curry did it twice. Still going. Kobe did it three times. Jerry West twice. Sam Jones once. Hal Greer once. That's the entire list. Now the NBA is different. We have more three -pointers now. It's easier to score. Scoring is the easiest it's ever been. Guys can play at a longer age. So I'm not ruling out Dane being good for the next three years. But just pointing out, history is saying, be a little nervous. In general with guards, like Chris Paul, we saw from age 35 to 36 to 37, like it just dropped. But that's two years older than Dane. Maybe it's fine. I just worry about guards. We have not a lot of instances with guards in their mid -30s of them either peaking as players or being able to sustain whatever success they had during their prime. It always starts to go down with really no exceptions, except for Steph Curry. He's the only non -exception. So if your case is Dane's as good as Steph Curry, or Dane can be as potent as Steph Curry on a winning team, like, you know, Steph Curry is better than Dane, but I'm not going to argue that he couldn't do a lot of the stuff that Curry did in Golden State. The bigger issue for me, the age I'm definitely worried about. Dane has not been healthy the last couple of years, and we have not seen him play nine straight months at playoff basketball with a big bullseye on his back. Everybody coming after you, you're the best team. We haven't seen him do that ever, much less than the last couple of seasons. So can he stay up? Can he stay healthy? That's one thing. The defense with Dane just got kind of swept under the rug the last couple days, and I don't really understand it because there's five categories of defensive player I feel like. There's excellent, there's good, there's average, there's not so good, and then there's bad. And I think Dane's a bad defender. I think the stats back it up. Like, his defensive rating last year was 245 out of the guards. He's the 245th guard for defensive rating. You know, 117 .4 individual defensive rating is 483 overall. Portland's team's always defensively, it was the Achilles heel for them. Partly because of Dane, because he couldn't guard anybody. He's too small. And, you know, think about what we saw from the playoffs the last couple years. I think about the 2020 bubble Celtics playoffs, not infrequently, because I think that team had a chance to potentially win a title. What happened? Everyone hunted Kemba Walker. It was hunting season. It's like, where is he? Got to get a switch. Got to get Kemba Walker guarding somebody who's bigger, or got to beat him off the dribble, and it just became a hunt session with him. And basically, he got played out of the league. He's not in the league anymore. You know, we had this with Isaiah Thomas, too, in the mid -2010s. I think it's been an issue with Kyrie Irving. The Celtics certainly went at him in the playoff series with Brooklyn a couple years ago. Curry, you saw, who I think is a better defender than people give him credit for, but the And he's a much better defender than Dame is. Jordan Poole is somebody that got hunted in playoff series recently. Chris Paul, obviously, is a big one. Jalen Brunson, remember what the Heat did to him? Mitchell, when he was on Utah, this was a huge issue. And then Trae Young, obviously. My fear with Dame is he's a DH, and I think in Portland, part of the reasons he was able to put up the stats he did was because he wasn't playing defense, right? It was just, how many points can I score? My team isn't very good, and I'm just going to do my thing. He's an incredible offensive player. But how much of a trade -off is the defense, right? Well, you think, all right, well, Milwaukee, they're really good defensively. They'll be able to protect him. Here's the team. Giannis, Dame, Lopez, Portis, Middleton, Conaton, Beauchamp, Crowder. Who's guarding Trae Young on this team? Who's guarding Jason Tatum? Here's a partial list of guys that I don't think this team will be able to guard this season. Devin Booker, Tatum, Butler, Trae Young, Kyrie, Curry. Who's going to be chasing Curry around the screens? Dame lowered? Good luck. SGA, Luca, Mitchell, Murray, Edwards, Brunson, Ja, Garland, Fox, Halburn. Are they going to be able to cover Derek White? I don't know. The way this team is constructed, they are not going to have the ability to guard other guards at all, which means they're just going to have to be in a shooting match with them, right? It's going to be not much different than what's going to happen with Phoenix, where they're just literally going to have to outscore the other team. I've just watched too much playoff basketball over the last couple years, where it's like, if you have that weak link on defense, and you're playing a team that's smart enough, they're going to go after that weak link. Like, think about them against the Lakers, right? The Lakers figure their crunch time. Let's say they make the finals. It's Milwaukee and the Lakers, and Lakers crunch time. They're going to have LeBron and Davis and Austin Reeves and, I don't know, a shooter and a point guard, whatever. All they're going to be doing is trying to find where Dame is on the court and going after him. What about when they play Boston? Boston puts out White and Brogdon and Tatum and Brown and a center, and all they're going to be doing is trying to make sure Dame is covering somebody who has the ball who's now torturing him. I think it's a real problem for them. And what's funny is they gave up Drew's defense and, you know, they, what they gave up on defense, which is significant, and they gained an offense, it might end up just being a wash and they might just be a different version of the same team where they still have a huge flaw. It's just on the other end of the court. I'm just shocked that nobody brought up the defense. I agree he's an amazing offensive player and what's cool about this trade and what I'm excited about as a basketball fan is, can he go up a level? Right? A lot of these stats he put up, especially the last couple years. They didn't mean anything. They were, he was on bad teams. Like, who cares? Ultimately, Bradley Beal scored 30 points a game on the Wizards. Who cares? I think most really good offensive players, if they're on a bad team, can get between 25 and 30 a night. Can you do it nine months in a row? Can you do it when you're getting hunted on defense all over the place? How much can Milwaukee protect him? And what does he have in the tank at age 33 with 900 plus games on the O 'Dominor already? I'm still afraid of the Bucks, but people have, like, FanDuel had them as best odds in basketball and I think most people feel like they're the favorite now. I don't feel like there's a favorite. I think you can go through every team. Boston, I could, I'm scared of Porzingis. What's going to happen with Jalen Brown out there? He has contracts. Can Peyton Pritchard, all these different things. Philly, God only knows. Miami, they're unquestionably worse. Yeah, Milwaukee is going to be really good, but depending where Holiday lands and how this all plays out, I just think it's still wide open. And the other piece, so if you're just talking Boston, Miami, Tatum kills Milwaukee. I have no idea why. Boston is kind of built to at least stay with Dame and, you know, Derek White is about as good of a person you're going to have to try to keep Dame in check, at least. And Boston's done a really good job of guarding Giannis over the years. They don't have Grant Williams this year, but I just don't think, I think there's as many ways this goes wrong as it goes right, I guess would be my final thought on this because for what they gave up, especially with that 29 unprotected and the two swaps and, you know, they are all in on this team. And you know my theory, when you go all in on a team, you better think you can win. Not positive, but it's an awesome trade. It really is. It makes the league so much more fun. Dame and Giannis together. I'm going to enjoy watching Portland. I still have my eating stock. Watching Phoenix fans slowly realize that Derkiszna isn't the answer is going to be fun and then we'll see where Drew Holliday goes. So really fun trade. We're going to talk about it a little bit more with Die Hard Bucks fan, Ben Thompson in one second. Let's take a break.

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