4 Rapid-Fire Trade Deadline Thoughts
Some teams made smart moves, some got a little creative and some didn't do much at all.
Thanks to all who joined Molly and me on our wild two-hour trade deadline chat Monday night. We had a lot of fun, even if we had no idea what was going on. We are now less than a week away from the launch of The Joy of Baseball podcast — we recorded another episode on Tuesday — and we can’t wait to share with you.
If you are a member of The Clubhouse or a paid subscriber to Molly’s awesome The Long Game newsletter, you will be automatically given a free year subscription to the JOB experience, where we’ll be doing all sorts of fun chats and live events and other stuff.
Three other quick things. One, CNN has started releasing its Decades in Sports documentary series — they released the 1960s and 1970s on Sunday and will release the 1980s, ‘90s, 2000s and 2010s every Sunday over the next month. The series is a lot of fun and, yeah, I’m in it a lot — or at least I’m in the first two a lot.
Two, here’s another reminder that Mike Schur and I will be introducing and discussing “A League of Their Own” at the American Cinematheque PodCasting Film Festival in Los Angeles on August 20. We are about to start the JoeBlogs baseball movie countdown; I’m hoping to time that so I can announce No. 1 on that day. Anyway, we’ll be at the Aero Theater, and tickets are available here.
Finally, the new Ted Lasso season has started, and while I have not been a particular fan of the show since Season 1, the first episode of this season has a wonderful scene about the Negro Leagues Baseball Museum, so that’s well worth watching.
OK, under a bit of a time crunch today, so I’m going to rapid-fire a few trade deadline thoughts. Here we go!
I like what the Red Sox did.
Shortly after the Red Sox traded three prospects — including one of the fastest rising prospects in the game, 21-year-old pitcher Anthony Eyanson — to Baltimore for Adley Rutschman, a somewhat panicked Mike Schur sent me this somewhat panicked tweet:
So, I have a very strong opinion about this … I think this just might be the most Boston talk-radio, Liam from Lexington, Sean from Sherborn, Paul from Peabody, hot-take nonsense reactions I’ve ever seen. I don’t mean that the trade is good for the Red Sox. I have absolutely no idea how it will turn out. There are a million factors involved, including health and development and luck and a bunch of other things.
But it is beyond absurd to say that the Red Sox trading a fast-rising pitching prospect who wasn’t even in Keith Law’s Top 100 when the season began, a 21-year-old pitcher with a 5.26 ERA in high A ball and a 19-year-old lottery ticket for a three-time All-Star catcher who, not so long ago, was viewed as one of baseball’s franchise players can possibly be “literally one of the most ridiculous trades I’ve seen in 30 years.”
Scouts fall in love with prospects. We all know that. We’ve all read and seen “Moneyball.” They sometimes fall so deeply in love with prospects that they lose all perspective. All three of those Red Sox players might end up in the Hall of Fame; but that’s the trap. They can become anything. As a writer, I call it the empty page conundrum. An empty page might become “The Great Gatsby.” It might become a shopping list. It might become a series of terrible jokes that you put together in a book that you hope people will read on the toilet. It might become a paragraph that is so embarrassing, you can’t hit delete fast enough.
It probably won’t become The Great Gatsby.
Let’s say that Eyanson ends up being the No. 9 prospect in baseball by year’s end. We don’t know — Keith has him No. 21 right now — but let’s say that’s where he ends up. Here were Major League Baseball’s No. 9 prospects in the 2010s:
2010: Justin Smoak
2011: Jesus Montero
2012: Trevor Bauer
2013: Gerrit Cole
2014: Kris Bryant
2015: Joey Gallo
2016: Joey Gallo
2017: Tyler Glasnow
2018: Forrest Whitley
2019: Alex Kiriloff
You might get Gerrit Cole, maybe. You might get Forrest Whitley or Alex Kiriloff. And that’s the NUMBER NINE PROSPECT IN ALL OF BASEBALL. Prospects are, almost always, overrated. This isn’t necessarily because they don’t live up to their baseball potential. Sometimes they don’t. But also Injuries happen. Aging happens. Life happens. Kris Bryant lived up to his potential for sure — he won Rookie of the Year and MVP in his first two seasons. Then came the injuries and the slumps and all the rest.
The other side of this Red Sox trade tells the story — four years ago, Adley Rutschman was utterly untouchable in trade talks. You couldn’t even ask about him. Rutschman was the Orioles’ franchise player — a switch-hitting, five-WAR catcher who hit with some power, played great defense and was a natural leader. The Orioles won 101 games with one of the youngest teams in baseball, and Rutschman was at the very heart of the good vibrations.
Then came some injuries and power slumps and all the rest, and at 28 he’s still a GOOD player — heck, he made the All-Star team this year — but the shine is off, and the Orioles readily traded him away for future hope. I happen to think that the Red Sox did well here, that Rutschman needed to get out of Baltimore, and that playing on a contending team will pick him up. But we’ll have to see.
What I can say now is that the Red Sox, for the first time in a long while, actually pushed in some chips, took on some money, and are trying to win. I know it’s in the DNA of many Red Sox fans to see impending doom. But I really think this is a good thing.
On the Brewers’ failure to launch.
A few years ago, the Kansas City Royals traded away Wil Myers — a consensus Top 5 prospect — to Tampa Bay for Big Game James Shields. They also picked up a tall right-handed starting pitcher who hadn’t lived up to his potential (we’ll get back to that). The Royals were pretty unanimously mocked for the deal, and it was easy to understand why. I called up Kansas City’s general manager, Dayton Moore, to ask him to explain.
And I will always remember his answer, which, essentially, was this: If you’re going to build a winning team, then at some point you have to get out of development mode and move into contending mode.
I have come to believe this with all my heart. It drove me absolutely bananas that the Orioles refused to get out of development mode. They had so many great prospects, and they decided to believe in all of them. That just won’t work. They needed to identify which prospects they REALLY believed in and which prospects they SORT OF believed in, and they needed to deal those sort-of prospects when their value was at its highest. If they had decided to trade Jackson Holliday when he was the No. 1 prospect in baseball, they could have gotten just about ANYTHING for him. They chose to believe in him. Maybe he will still emerge; he’s only 22. But the chances grow fainter every year. That’s true for all their prospects. And now they’re starting over.
The Royals got lucky with the Myers deal. That tall right-handed pitcher never did live up to his potential, but the Royals put him in the bullpen, and Wade Davis, as much as anyone, led the team to back-to-back pennants and a World Series championship. But even if that had not happened, I believe Dayton Moore was right. The Royals were never going to get there if they just relied on their own prospects turning into stars.
This leads us to the Milwaukee Brewers — this is an astonishing organization. Year after year, they are underestimated. Year after year, they win. They have a special knack for developing good everyday players like Brice Turang and Jackson Chourio and Garrett Mitchell and Cooper Pratt. More, they are wizards at developing star pitchers — I mean, just this decade, there’s Corbin Burnes and Brandon Woodruff and Freddy Peralta and Devin Williams and Josh Hader and, of course, now Jacob Misiorowski.
These guys know what they are doing. And the Brewers have made the playoffs in seven of their last eight seasons and will almost certainly make it again this year.
But those playoffs have been huge disappointments, particularly the last three years. Last year, they squeaked by the Cubs in the Division Series only to get swept by the Dodgers — scoring just four runs in four games. In the previous two years, they lost in the wildcard round.
And, look, baseball’s playoffs are a crapshoot — there isn’t anything you can do to GUARANTEE postseason success. But that doesn’t mean you stop trying. There was a very clear mission for the Brewers this trade deadline: They HAD to get a dominant left-handed starting pitcher. They just HAD to. The Dodgers don’t have any obvious weaknesses, but the real power of their lineup is left-handed — Shohei, Freddie, Muncy. The Dodgers are, far and away, the best-hitting team against right-handers. They’re a bit more vulnerable against lefties.
This is certainly one of the reasons the Dodgers traded for Tarik Skubal. This was like when Bear Bryant used to recruit some of the best high school football players in America, even when he had no place for them on his roster. He was just keeping them away from the other college football powerhouses.
The Brewers needed to win that Skubal battle, though.
There are now reports that the Brewers did put together a serious offer for Skubal, perhaps offering 19-year-old shortstop Luis Peña, who is a top 25 prospect. Maybe they did. That seems to be what they’re floating now. Maybe they put together an offer that was, at least arguably, better than what the Dodgers put out there.
Of course, maybe they didn’t.
Either way it doesn’t really matter. The reality is, they didn’t get Skubal.
And they needed to get Skubal.
Whatever it took.
Well, wait — how far does “Whatever it takes” go? The Brewers have perhaps the No. 1 prospect in all of baseball, 19-year-old Jesús Made. Certainly, dealing him would have locked down two months of Skubal, but that would have been malpractice, right?
Right. It would have been malpractice.
BUT … we’re back to the empty page conundrum, right? Jesús Made could be anything. He could be the league MVP. He could be Jurickson Profar. He could be the star who takes Milwaukee, finally, the title. He could be Yoan Moncada.
It’s possible that the Brewers would have forever wrecked the franchise by trading Jesús Made for a Skubal rental.
It’s also possible that Jesús Made will never be more valuable than he is right now.
I’m certainly not saying they should have traded Made. What I am saying is they should have at least thought about it. What I am saying is that they needed to outbid the Dodgers. They could not afford to lose the Skubal sweepstakes, and they did anyway. At some point, you have to get out of development mode and take a real chance. Instead, you end up here — with Brewers fans left to wonder just what a playoff series against the Dodgers might have looked like with Jacob Misiorowski and Tarik Skubal pitching on back-to-back days.
The A.J. Preller mindset
I kept hearing that the Padres were going to be sellers this trade deadline. Instead, they picked up Robbie Ray and Casey Mize; they held on to Mason Miller and Adrián Morejón; they have decided that even though they’re a game out of their wildcard spot right now and the Dodgers look indomitable, they’re going for it.
I’ve not always been a particular fan of the way A.J. Preller runs the Padres … but I admire this part of him: He’s as competitive as can be, and he looks at his faulty club and thinks: “With our dominant bullpen and Miller on the back end, we are a scary matchup in a short series.”
I don’t know that he’s right. To win games, you have to score runs, and the Padres don’t. But I like the fight. And, hey, he could be right. Baseball would be better if more GMs tried to win.
Cleveland goes for it (sort of)
The American League Central is like its own pocket universe. You’ve got five flawed teams bouncing around like lottery balls in that glass ball. The White Sox have three sluggers — Munetaka Murakami, Miguel Vargas and Colson Montgomery — popping enough home runs to keep them above .500 and in first place. The Twins are hitting a few home runs too, but not enough to get them to the top. The Tigers have given up the ship by trading Skubal and Mize, but they might win the division anyway. Kansas City has fallen off the edge.
And that leaves Cleveland, the team that always seems to find a way to win this division. The Guardians had to play more than a month without José Ramírez, and he has looked helpless since he has returned, so that’s a real challenge — over the last decade, Ramírez has probably meant more to the Guardians than any player has meant to any team.
But Cleveland did try to boost the club with some minor deals — except minor deals in this pocket universe can turn out to be major deals. The Guardians picked up Joe Adell, who hit 37 home runs last year. They picked up Nathaniel Lowe, who is crushing righties this year. And they got Foster Griffin, who has found himself at age 30 and after playing three seasons in Japan — he’s 12-3 with a 3.06 ERA.
None of these guys would likely be a game-changer in any other division.
But in the AL Central? Who knows?




"A boat's just a boat, Lois. But this mystery box could be anything! It could even be a boat!"
-Peter Griffin
Love the analogy of the blank page for the prospect. Ordinarily, and I think this is still true in the AL, just getting into the playoffs and hoping things go your way is a viable strategy for an organization. However, the Dodgers are so loaded that Dave Roberts can manage the entire season with the postseason in mind which makes them so good that an opponent needs to be better than usual or really lucky. As Khazad pointed out this week, it doesn't mean a small or mid-market team can't pull it off, but to do it, they will likely have to maximize their talent when the wave is cresting by extending some key players, signing a free agent or two, and/or pulling off a significant trade deadline deal. This would them a top 10 payroll or close to it for a short time, which may be uncomfortable for ownership, but is probably going to be necessary for a realistic chance of beating high payroll teams in the playoffs and winning a championship.
On the flip side, would be the argument just made the other day by Joe in response to the Brewers' fan despair...the Brewers are providing their fans with entertaining baseball and championship hope year after year. It could be argued that it isn't worth disrupting that by going all-in, have it fizzle, and then go through a painful rebuild back to where you started. I personally agree with Joe's take today.