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2019 MLB Trade Deadline: Who lost the day?

Every front office is smart now, but that didn’t keep some organizations from having a bad deadline.

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Divisional Round - Boston Red Sox v New York Yankees - Game Four Photo by Jim McIsaac/Getty Images

With MLB front offices becoming increasingly homogeneous, picking out the losers of the deadline has become slightly more difficult. Lopsided trades are a dying out as information spreads and teams get smarter. Gone are the days where a team steps in a bucket, trades Fernando Tatís, Jr. for James Shields, and leaves us saying, “Wait. No. What are you doing?” However, the practice of second guessing people smarter than us is an eternal tradition for baseball fans. Come. Let us second guess these smart people.


The Yankees were dead set on acquiring a frontline starting pitcher and came away with nothing. The Mets swooped in on Marcus Stroman, and a three-team stunner sent Trevor Bauer to Cincinnati. There were reports that the Yankees were close to a Clint Frazier for Robbie Ray deal but were unwilling to throw in the additional prospects to get it done. They were supposedly on the phone with the Giants about Madison Bumgarner all morning, and they were negotiating for Zack Greinke into the final minutes before he ultimately went to New York’s greatest competition for the AL Pennant: the Astros.

The Yankees’ inaction is symptomatic of MLB’s “prospects over parades” mentality. There were several rental starters and relievers who didn’t move this offseason because no one wanted to cough up the prospects necessary to get them. It’s impossible to know if the asking prices for Ray, Madison Bumgarner, and Zack Wheeler were absurd or not, but generally the prospects that move in deadline deals aren’t anything to get excited about. The Yankees absolutely could have matched the price for Marcus Stroman or at the very least Tanner Roark or Aaron Sánchez.

The Yankees might be talented enough to stand pat and coast their way to a division title, but so were the Astros, and they made themselves a whole lot better.


“Loser” is a bit of a misnomer for the Padres who made a move with enormous upside but wasn’t without equal risk. This deadline will be defined by their role in the Trevor Bauer trade. San Diego sent Franmil Reyes and Logan Allen to Cleveland in exchange for Taylor Trammell. Reyes is an already proven major league hitter, and Allen’s floor is a back-end starter. The Padres are essentially buying high on a prospect whose stock is falling. It’s not clear that Trammell can stick in center field, and the power hasn’t developed yet.

There’s still a chance for Trammell to be a star and make the Padres look like geniuses, but there’s also the risk that Trammell doesn’t match the production that Reyes is putting out now, not to mention what Allen can do. With the amount of talent coming up through the Padres system, they have a bit of a roster crunch coming up. The Padres felt they could part with Reyes. He’s not a good defender, and his on-base skills are suspect, but the power plays anywhere.

Even if Trammell becomes the player A.J. Preller thinks he can be, he still won’t realistically be major league ready by 2021. By signing Manny Machado, bringing up Fernando Tatís, Jr., and starting the year with Chris Paddack, the Padres signaled that they were ready to start competing, but swapping out Reyes for Trammell delays that.


The Dodgers made two moves at the deadline. Los Angeles picked up the currently-injured Jedd Gyorko to provide insurance for the also-injured Chris Taylor, David Freese, and Kiké Hernández. They also acquired Adam Kolarek from the Rays to bolster their bullpen. The Dodgers are in the same position as the Yankees, but are even more assured of a division title, and they’re the clear favorites in the National League.

Still, their roster isn’t without its weakness. The bullpen has been just about average. Kenley Jansen has been nowhere near as automatic as he was two years ago. Joe Kelly has been better lately, but beyond him, there are a lot of question marks. The Pirates’ ask for Felipe Vázquez was prohibitively high, and Kolarek is a fine reliever, but not doing anything else shows either a lack of creativity or uninspiring risk aversion.

Blue Jays

The Blue Jays were one of the most active sellers, and they certainly came away with some fine players, but it really seems like they should have gotten more. The return for Marcus Stroman left many scratching their heads, and it looked even worse in comparison to what Cleveland got for Trevor Bauer. Cleveland came away with a major league-ready power hitter who is under control for several more years, two months of Yasiel Puig to help them chase down the Twins, a promising pitching prospect, and two raffle tickets. The Blue Jays got a couple pitching prospects who are pretty good if you squint.

They weren’t going to get a lot for Aaron Sánchez, so they threw in Joe Biagini and Cal Stevenson and got back Derek Fisher. Fisher has had three chances to stick in the majors but owns a .281 wOBA in 312 career plate appearances.

The returns for David Phelps, Eric Sogard, and Daniel Hudson seem appropriate, but these weren’t the big chips Toronto had. If they screwed up the Sogard trade, no one would have noticed.

Kenny Kelly is a writer for Beyond the Box Score and McCovey Chronicles. You can follow him on Twitter @KennyKellyWords.