Yankees, Dodgers & Red Sox Among 5 Biggest Trade Deadline Losers

Ben DiGiacomo
Host · Writer
The MLB trade deadline has come and gone, with plenty of teams attempting to set themselves up for a strong playoff push. Many teams swung and missed, with these five teams, in particular, coming out as the biggest losers of the deadline.
To get all the MLB trade deadline analysis, check out SportsGrid’s MLB trade deadline tracker and grades.
MLB Trade Deadline: NL Wild Card Impact | Both Teams Got Better | Wrong Decisions | Futures Impact
Los Angeles Dodgers
In what felt like a gap year for the Dodgers, they’re in the thick of the World Series race. While their starting pitching has taken a step back, the young guys in their lineup and bullpen have performed well, with their well-paid offensive pieces playing up to their salaries. Still, sitting behind the Atlanta Braves in the NL pecking order, the Dodgers did nothing to give themselves a chance to overcome that.
Dumping Noah Syndergaard for Amed Rosario was wise, given Thor’s struggles, but replacing Syndergaard’s spot in the rotation with Lance Lynn is underwhelming. Then, trading for Eduardo Rodriguez just for him to decline was an absolute disaster, as they were left out to dry as the trade deadline expired. Even though seeing someone saying no to the Dodgers probably caught the front office with their pants down, they still have to be aware of a guy’s no-trade clause and have a pivot in place to ensure they aren’t left empty-handed, which they were.
New York Yankees
The Yankees were on the outside looking inward on the playoff hunt anyway, currently sitting in last place in the AL East but only 2.5 games back of the final wild-card spot. They’ve disappointed in 2023 with a season filled with injuries and players regressing.
We didn’t necessarily believe that the Yankees should have gone all-in with this bunch. But the Yankees are still the Yankees, so seeing them throw in the towel is odd. Acquiring Kenyan Middleton will help their bullpen, but it was already a strength. Not adding a bat or another starter, especially with Domingo German now out indefinitely, is what a team in a small market does, not the New York Yankees.
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Boston Red Sox
Sticking in the AL East, the Boston Red Sox are only half a game in front of the Yankees, but they didn’t do anything worth noting. The Red Sox dumped Kike Hernandez as their lone move, a non-impact trade.
Like New York, they are on the outside looking in, but seeing the Red Sox stand pat as the Baltimore Orioles, Tampa Bay Rays, and Toronto Blue Jays all make sizable moves for the playoff hunt is strange. Maybe the Red Sox shouldn’t have gone all-in given their playoff standing as the Los Angeles Angels did, but at least do something as a big market team so the feeling in the clubhouse isn’t “they don’t believe in us.”
San Francisco Giants
The Giants are the forgotten team in the NL, where despite having the third-best record in the league, no one pays them any attention. The sportsbooks aren’t taking them seriously either, with Philadelphia Phillies still being priced ahead of them in the NL championship odds, making the Giants a distant fourth at +1600.
They have a bunch of good players that are seemingly clicking on all cylinders, but no one is great enough to put them over the top, so many hoped they would buy at the deadline. Well, they bought AJ Pollock and his .169 batting average. The Giants feel like sitting ducks with the top spot with NL Wild Card contenders in the Phillies, Miami Marlins, Arizona Diamondbacks, Chicago Cubs, and even San Diego Padres buying at the deadline.
San Diego Padres
Speaking of the Padres…they did indeed buy at the trade deadline, but I’m still puzzled about why and for whom. Rich Hill is 44 years old, Ji-Man Choi is a below-average offensive player, and Scott Barlow is having a down year. What difference will they make?
If the Padres chose to sell, as they should have, they could be sitting on a war chest of prospects right now. Blake Snell, Josh Hader, and Juan Soto would have been the best starter, reliever, and position player on the market, making it a missed opportunity for San Diego to completely restock their farm system when their playoff chances are slim.
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