MLB's Worst Moves Since 2020: The 30 Biggest Blunders

A look at the 30 worst moves by MLB teams since 2020, ranked from least to most damaging.

This is no secret: Front offices are smarter than ever and, believe it or not, make fewer mistakes than ever. Fewer big mistakes, at least. Consider some of the players traded as prospects last decade (from 2010-19): Yordan Alvarez, Zack Wheeler, Max Fried, Trea Turner, Luis Castillo, Sandy Alcantara, Zac Gallen, Dansby Swanson, Fernando Tatis Jr., Dylan Cease, Anthony Rizzo, Patrick Corbin, Lucas Giolito, Willy Adames, Jesus Luzardo, Gleyber Torres.That's six of the top 12 pitchers this decade via WAR and five of the top 30 position players. Some of the deals worked out for the teams trading away the prospect: The Cubs won a World Series with Aroldis Chapman (traded for Torres) and the Nationals won a World Series with Adam Eaton (traded for Giolito) -- but most did not.We're halfway through the 2020s and we haven't seen nearly as many of those kinds of trades (so far, anyway). Top prospects are the gold currency of MLB, to be parted with only in acts of desperation. But mistakes have still been made: bad trades, bad signings, bad decisions in the playoffs. Stealing an idea from ESPN NFL writer Bill Barnwell, we're going to dig up the worst decision each team has made through these past five years, evaluating the outcome and not the process.We'll start with the least damaging of the moves and end with the biggest mistake so far of the 2020s.Jump to a team:American LeagueATH | BAL | BOS | CHW | CLEDET | HOU | KC | LAA | MINNYY | | SEA | TB | TEX | TORNational LeagueARI | ATL | CHC | CIN | COL LAD | MIA | MIL | NYM | PHIPIT | SD | SF | STL | WSH

What to Read Next

Post-Deadline MLB Fantasy Baseball: Top 7 Players to Watch
MLB

Post-Deadline MLB Fantasy Baseball: Top 7 Players to Watch

Discover the top MLB players to add to your fantasy baseball roster following the trade deadline. Get insights on rising stars and their potential impact.

How the San Diego Padres Dominated the MLB Trade Deadline: A.J. Preller's Bold Moves to Challenge the Dodgers
MLB

How the San Diego Padres Dominated the MLB Trade Deadline: A.J. Preller's Bold Moves to Challenge the Dodgers

Discover how A.J. Preller's aggressive trades at the MLB deadline positioned the Padres as serious contenders against the Dodgers.

2025 MLB Trade Deadline: Key Moves, Surprises, and Future Implications
MLB

2025 MLB Trade Deadline: Key Moves, Surprises, and Future Implications

A comprehensive look at the 2025 MLB trade deadline, highlighting key deals, surprising moves, and their impact on the future of baseball.

Historic MLB Speedway Classic: Braves vs. Reds Break Attendance Records in Tennessee
MLB

Historic MLB Speedway Classic: Braves vs. Reds Break Attendance Records in Tennessee

The Atlanta Braves and Cincinnati Reds made history at the MLB Speedway Classic in Tennessee, drawing a record-breaking crowd of over 85,000 fans.

Sunday MLB Fantasy Baseball & Betting Guide: Expert Tips & Lineup Strategies
MLB

Sunday MLB Fantasy Baseball & Betting Guide: Expert Tips & Lineup Strategies

Get expert advice on setting your MLB fantasy baseball lineups and betting tips for Sunday's games. Includes starting pitcher rankings and hitter insights.

MLB Week 19 Fantasy Baseball Guide: Pitching Debuts, Hitter Ratings, and Schedule Insights
MLB

MLB Week 19 Fantasy Baseball Guide: Pitching Debuts, Hitter Ratings, and Schedule Insights

Get ready for MLB Week 19 with our comprehensive fantasy baseball guide, featuring pitching debuts, hitter ratings, and key schedule insights.

MLB Trade Deadline 2025: Surprises, Strategies, and Season Predictions
MLB

MLB Trade Deadline 2025: Surprises, Strategies, and Season Predictions

Explore the biggest surprises and strategic moves from the 2025 MLB trade deadline, and get insights into which teams are poised for success in the upcoming season.

MLB Power Rankings 2025: Post-Trade Deadline Team Standings and Analysis
MLB

MLB Power Rankings 2025: Post-Trade Deadline Team Standings and Analysis

Explore the latest MLB Power Rankings after the 2025 trade deadline, featuring in-depth analysis of team standings and key player moves.

MLB 2025 Trade Deadline: Winners, Losers, and Key Moves That Shaped the Season
MLB

MLB 2025 Trade Deadline: Winners, Losers, and Key Moves That Shaped the Season

An in-depth analysis of the 2025 MLB trade deadline, highlighting the biggest winners, losers, and key transactions that are set to impact the season.

Master Your MLB Friday: Expert Fantasy Baseball Lineup Strategies & Betting Insights
MLB

Master Your MLB Friday: Expert Fantasy Baseball Lineup Strategies & Betting Insights

Get the ultimate guide to setting your fantasy baseball lineups and placing smart MLB bets for Friday's games with expert analysis and betting tips.

Mariners' Bold Moves at Trade Deadline: A World Series Push
MLB

Mariners' Bold Moves at Trade Deadline: A World Series Push

Seattle Mariners' president Jerry Dipoto believes the team's aggressive trade deadline moves, including acquiring Eugenio Suarez and Josh Naylor, have positioned them as serious World Series contenders.

Cincinnati Reds Strengthen Lineup with Strategic Acquisition of Miguel Andujar from A's
MLB

Cincinnati Reds Strengthen Lineup with Strategic Acquisition of Miguel Andujar from A's

The Cincinnati Reds enhance their roster by acquiring versatile player Miguel Andujar from the Athletics, aiming to boost their performance against left-handed pitchers.

Tampa Bay Rays Boost Pitching Rotation with Adrian Houser Trade from White Sox
MLB

Tampa Bay Rays Boost Pitching Rotation with Adrian Houser Trade from White Sox

The Tampa Bay Rays have strengthened their pitching lineup by acquiring Adrian Houser from the White Sox, adding depth and experience to their roster.

Top 10 MLB Players Poised for Blockbuster Trades Before Deadline
MLB

Top 10 MLB Players Poised for Blockbuster Trades Before Deadline

Explore the top 10 MLB players most likely to be traded before the 2025 deadline, featuring key insights and potential destinations.

MLB Trade Deadline 2025: Last-Minute Moves, Key Players, and Team Strategies
MLB

MLB Trade Deadline 2025: Last-Minute Moves, Key Players, and Team Strategies

Get the latest insights on the 2025 MLB trade deadline, including potential moves for key players like Eugenio Suarez and Dylan Cease, and team strategies from experts Buster Olney and Jeff Passan.

Load More

We use essential cookies to make our site work. With your consent, we may also use non-essential cookies to improve user experience and analyze website traffic. By clicking "Accept," you agree to our website's cookie use as described in our Cookie Policy.