Monday, August 3rd, 6 PM Eastern. The 2026 MLB trade deadline.
A trade deadline used to loom on the horizon like a Leviathan just beneath the surface. It would emerge and reshape the entire pennant race as all-stars on ending contracts were reshuffled from the bottom of the league to the championship contenders. Sometimes creating super teams, like the 2017 Astros, where the addition of Verlander and a few well-placed dugout trash cans were enough for Houston to steal a championship.
I still follow the deadline closely, watching Foul Territory post videos each day with the latest rumors, reading articles online about who might go where.
The big fish this year is Tarik Skubal. He’s on a surging Detroit team that just a couple months ago wasn’t certain he would be pitching again this season. The combination of his return to action, Kevin McConigle’s hot bat, and Spencer Torkelson’s rise, 15 homers on the year thus far, have the Tigers in a precarious position. Just a handful of games out of the final Wild Card spot, with their playoff odds sitting somewhere in the 20-25% range depending on who you ask. In the last 24 hours Skubal’s odds of being traded on Kalshi have grown from 65 to 70%, but a 7/10 chance of trade for a guy that is guaranteed to walk after this is surprising. A weak American League that still feels wide open is another culprit in this landscape as well. Could they be foolish enough to hang onto Skubal and get nothing in return? Only the Angels could have pulled something like that off, and they did in a sense when they could have moved Ohtani for a king’s ransom before the 2023 season, but held on, he got hurt, and they got nothing. But more on them later.
The impact of the expanded postseason on the trade deadline can’t be understated. It is one of several factors that has rewritten how the midsummer major league musical chairs play out. With two additional Wild Card spots, significantly more teams are in contention this time of year than would have been before. My old friends, the Boston Red Sox, who have had a disastrous year by all accounts and expectations, sit just 2.5 games back from the third Wild Card spot. They sit at 43-48 today, a better record than the vibes and the Boston media coverage would indicate.
While they have found some momentum lately, including a recent sweep of the Yankees, they have no business considering themselves buyers at this deadline. But the slim possibility of a returning Crochet and Anthony, along with Craig Breslow’s desperation to save his general manager job, could have them thinking twice at the deadline three weeks from now.
The Red Sox need to sell; starting with Sonny Gray, Aroldis Chapman, and Jarren Duran. Restocking the cupboard that has borne less fruit than expected with the triumvirate of Roman Anthony, Marcelo Mayer, and Kristian Campbell — from varying degrees of disappointment to disaster — should be the priority. The faltering young core has them much further away from a championship window than it appeared just four months ago.
Breslow is also proof positive of the harm playing fast and loose at the trade deadline can do to a team. He gave up James Tibbs for two months of the herbivore Dustin May, and then, this past offseason, sent Kyle Harrison — one of the top left-handed pitching prospects in baseball, owner of a 2.82 ERA that has swelled a bit after a few recent rough starts, and the headline piece coming back in the Devers deal — to Milwaukee for Caleb “What is baseball?” Durbin. I think Caleb knows what baseball is, but he doesn’t often play like it.
The expanded Wild Card slots are not the only factor in why the motion at the deadline is down. Prospects are now hitting the big leagues in stride thanks to a multitude of reasons. Young starlings like Kevin McGonigle, Konnor Griffin, and a wave of other rookies forcing their way into everyday lineups are having an enormous impact upon arrival. Pitching machines that can replicate major league arms, pitch sequences, and velocity have shortened the learning curves for young players in a major way. Parting with a young and desirable prospect is giving up what might be a valuable and cost-controlled near- and long-term asset for a little extra postseason juice for one season.
There has been a glimmer of hope for how the trade deadline can get its mojo back. Part of a recent proposal by the owners to the MLBPA included the ability to trade future draft picks (I’ll cover the likelihood this labor dispute kills the 2027 season in greater detail in a future post). It’s something that seems absurd that it isn’t already possible. Adding the ability to trade future draft picks adds immediate liquidity to the trade market. If a small-market team like Milwaukee wants to make a move to get this team over the hump for a World Series, trading future assets allows them to do so without parting with players currently in their farm system they covet. Seeing the Brewers trade five future first-round picks to shore up this year’s team to the point of getting a World Series title would not only be incredible to witness, it may change the calculus for how strongly small-market teams are able to compete in October. It would also be interesting to see how the wild big-market big spenders like the Mets — who seem willing at times to completely throw caution to the wind in pursuit of success ($42 million a year to Bichette anyone?) — and the “I Ain’t As Good As I Once Was, But I’m As Good Once As I Ever Was” Phillies (they owe $647m to players age 33 and up) would use that new currency to mortgage their futures and truly push their chips in for a title.
Just 24 days out from this year’s deadline, we may not have seen the last of the fireworks for America 250, but we may see more alligator arms from GMs who aren’t ready to truly play their hand. If this deadline is another dud, at least there’s hope for more electric moves at the wire in the future.
Whatever happens, I don’t think anything could be more absurdly amusing than when the Angels were both hot and cold at the buzzer in 2023 — buying Giolito, Lopez, Leone, Cron, and Grichuk before the deadline, then turning around a month later and putting four of them on waivers just to dump the salary, getting absolutely nothing back for any of it. That’s not strategy, that’s just Angels baseball. There’s only one Arte Moreno.
