Ranking the Worst Offseason MLB Trades Since 2000

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Miguel CabreraM. Spencer Green/Associated Press

Roster management is mostly an educated guess. Nobody can be certain about a player’s future production, but MLB scouts and executives believe in their evaluations.

Every year, those assessments lead to offseason trades. Hopeful contenders pad their lineup and rotation for a championship run, and rebuilding teams part with key contributors in exchange for prospects and a brighter long-term outlook.

Not every decision pays off, though.

Big-name players struggle in a new location, or top prospects don’t develop as expected. The buying team trades a future star, or the selling franchise gives away incredible value for little in return. And some cases result in an awful combination of those outcomes.

The last two decades are littered with unsuccessful moves, and we’re remembering the worst MLB offseason trades since 2000.

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David Zalubowski/Associated Press

Not enough time has passed to declare this 2021 transaction a flop for the Colorado Rockies, but it certainly isn’t a promising one.

Colorado sent Nolan Arenado, already an eight-time Gold Glover and four-time Silver Slugger, and $51 million to the St. Louis Cardinals. Although the Rockies probably would’ve lost Arenado to an opt-out decision after the 2021 season, he was an established superstar. And they didn’t even acquire a top-tier prospect in return.

Along with young pitcher Austin Gomber, Colorado added prospects Elehuris Montero, Mateo Gil, Tony Locey and Jake Sommers. None of them landed on B/R’s top 100 ranking at the end of the 2021 season, and only Montero even earned an honorable mention.

That is incredible in a horrible way.

Jeff Bridich—who orchestrated the trade—resigned as Colorado’s general manager three months later. Perhaps the prospects will develop into stars. For now, it’s a miserable memory that might get worse.

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KYLE ERICSON/Associated Press

The problem isn’t what the Atlanta Braves received in return. That’s why this December 2003 trade is a bit lower on the list.

J.D. Drew put together a superb year in 2004, hitting .305 with a career-best 31 homers. He finished sixth in the NL MVP voting. Eli Marrero contributed nicely off the bench, playing all three outfield positions and helping Atlanta win its 10th straight division title.

The issue is the Braves gave up Adam Wainwright, then a top prospect, in exchange for a failed World Series run. Drew and Marrero both lasted only one season in Atlanta and signed elsewhere as free agents.

Wainwright, meanwhile, lived up to his potential in St. Louis. He was on the mound for the final out of the 2006 World Series as a rookie before becoming a three-time All-Star, two-time Gold Glove winner and four-time top-three finisher in the NL Cy Young voting.

Even worse for Braves fans, Wainwright grew up in Georgia. The local product could’ve been a legend for his home-state team.

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Matt Slocum/Associated Press

When a reigning MVP is moved, you’d expect one franchise to thrive. In reality, the December 2017 deal that sent Giancarlo Stanton from Miami to New York has left a bitter feeling on both sides of the transaction.

From the Yankees’ perspective, the slugger hasn’t matched his billing. Stanton has a pair of 30-homer seasons in pinstripes, but the combination of strikeouts, injuries and little defensive value has soured the narrative of his tenure.

But, hey, at least the Marlins stockpiled their farm system, right? Stanton had landed the NL MVP in 2017, after all.

So far, not so good. Jose Devers and Jorge Guzman are no longer top prospects. While they may still develop into contributors, the Marlins are certainly hoping for more production than a platoon player and low-impact arm. Otherwise, the primary return is two adequate years from veteran shortstop Starlin Castro, who left in free agency in 2020.

Neither the Yankees nor Marlins look back on this trade fondly.

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NICK WASS/Associated Press

In July 2003, the Texas Rangers basically stole Adrian Gonzalez from the Florida Marlins. Too bad the Rangers similarly gave him up in January 2006 before realizing the returns.

Texas parted with Gonzalez to land starting pitcher Adam Eaton, reliever Akinori Otsuka and prospect Billy Killian from the San Diego Padres. Eaton struggled in one season with Texas, Otsuka pitched well but only stayed for two years, and Killian never advanced past High-A.

In fairness to the Rangers, Gonzalez—the No. 1 overall pick in the 2000 draft—hadn’t impressed in two brief Major League stints.

But he certainly did with San Diego.

Gonzalez won two Gold Gloves and thrived at the plate in five seasons. He averaged 35 doubles, 32 homers and 100 RBI per year for the Padres, peaking at fourth in the 2010 NL MVP voting.

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JEFF CHIU/Associated Press

While the Rangers dealt Adrian Gonzalez—a three-time All-Star in San Diego—in their flawed transaction, the San Francisco Giants parted with two separate All-Stars.

After the 2003 season ended, the Giants added catcher A.J. Pierzynski in a seemingly wise deal with the Minnesota Twins. Joe Nathan was an injury-plagued reliever, and neither Francisco Liriano nor Boof Bonser had pitched like future stars in the minors.

Pierzynski, however, played only one season in San Francisco and didn’t exactly endear himself to Giants teammates.

Bonser didn’t develop into much for Minnesota, but Nathan was a four-time All-Star and the franchise’s all-time saves leader. Liriano struggled to regain his form following Tommy John Surgery, yet he was still an All-Star as a rookie in 2006.

Fortunately for the Giants, three championships in the 2010s helped reduce the sting of the Pierzynski flop.

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Winslow Townson/Associated Press

Roy Halladay spent 12 seasons with the Toronto Blue Jays, making six All-Star teams and earning the 2003 AL Cy Young. But they never reached the playoffs, and it wore on Halladay to the point that he requested a trade out of Toronto.

“[Halladay] made it very clear: ‘I’m leaving. There’s nothing you can do to make me stay. You can offer me all the money in the world. I need to win. I want to win,'” then-GM Alex Anthopoulos said in the book Doc: The Life of Roy Halladay (h/t Rob Longley of the Toronto Sun).

So, the Jays did their best in December 2009. They landed three prospects: Kyle Drabek, Travis d’Arnaud and Michael Taylor.

Drabek—a first-round pick in 2006—was the prized addition from the Philadelphia Phillies, but he posted a 5.27 ERA across five seasons with Toronto. And while d’Arnaud recently won a World Series in Atlanta, he both never played for the Jays and was part of another messy offseason deal that sent Noah Syndergaard to the New York Mets in 2012. Toronto immediately flipped Taylor to the Oakland A’s, too.

On the other hand, Halladay won the NL Cy Young in 2010 and finished second in 2011. The right-hander capped his Hall of Fame career with two more All-Star appearances in Philly.

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ROY DABNER/Associated Press

Following the 2003 season, the Arizona Diamondbacks reshaped their roster with two blockbuster trades.

In late November, they sent All-Star pitcher Curt Schilling to the Red Sox for Casey Fossum, Brandon Lyon, Jorge De La Rosa and Mike Goss. Exactly four days later, Arizona basically shipped its entire infield plus Chris Capuano and De La Rosa to the Milwaukee Brewers for power-hitting first baseman Richie Sexson.

The trade obliterated the Diamondbacks.

Fossum and Lyon combined for 0.7 WAR in Arizona, and Goss never played in the majors. Sexson had a sensational April, but shoulder injuries limited him to 104 plate appearances in 2004. He joined the Seattle Mariners in free agency the next offseason.

Meanwhile, the D-backs—imagine this—struggled to replace a catcher, first baseman, injured first baseman, second baseman and third baseman. They plummeted from a potential contending team with 84 wins to a franchise-worst 51.

Schilling won two World Series in Boston, which included his iconic “Bloody Sock” performance in 2004. He was also an All-Star and Cy Young Award runner-up in that first year in Beantown.

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AARON J. LATHAM/Associated Press

Five years later in December 2009, the Diamondbacks mangled another trade.

Max Scherzer quickly rose through the Arizona system, debuting in 2008 and securing a full-time starting role in 2009. However, the D-backs sent him to the Detroit Tigers as part of a three-way trade with the Yankees for Ian Kennedy and Edwin Jackson.

Kennedy soon impressed for Arizona, finishing fourth in the NL Cy Young voting during his second year. He remains a top-10 pitcher (or so) in franchise history.

But that’s not enough to offset the loss of Scherzer.

Scherzer rose to prominence as the 2013 AL Cy Young winner and managed a fifth-place spot in the 2014 voting. Scherzer went 82-35 with a 3.52 ERA and two All-Star nods across five seasons with the Tigers, helping them reach the 2012 World Series, too.

Even excluding his post-Detroit career, that’s a major net-negative for Arizona. Throw in two NL Cy Young wins while with the Washington Nationals, and the D-backs traded a legend.

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J. Pat Carter/Associated Press

After determining they wouldn’t give Miguel Cabrera his impending raise, the small-market Marlins traded him in December 2007 to keep their payroll low.

Florida sent Cabrera and Dontrelle Willis to Detroit for top prospects Cameron Maybin and Andrew Miller, along with Burke Badenhop, Frankie De La Cruz, Mike Rabelo and Dallas Trahern. And the move shattered fans’ trust in the organization for a decade.

Already a four-time All-Star at just 24 years old, Cabrera became the AL’s most dangerous hitter. He won the Triple Crown in 2012 and a second straight MVP in 2013, notching six straight seasons of 30-plus homers and 100-plus RBI to begin his Detroit tenure. He’s one of the most productive players in franchise history.

As for the Marlins? It’s a dreadful memory.

Maybin and Miller both put together long MLB careers, but neither offered much during their three-year stay on the Marlins (2008-10). Maybin posted an 88 OPS+ in 557 plate appearances, and Miller had a 5.89 ERA in 220 innings. The other four players combined for 0.7 WAR during their time in Florida.