Some baseball trades don’t just move players between teams.
The most shocking deals in MLB history changed the entire landscape of the sport. They created dynasties in one city while leaving others in ruins for decades. These transactions sparked debates that continue today, with fans still arguing about what went wrong and who made the worst decision.
From Hall of Fame careers derailed to dynasty-defining acquisitions, these trades remind us that one bad decision can haunt a team for generations.
Let’s explore the trades that still make fans shake their heads in disbelief.
1920: Babe Ruth to the Yankees
The sale that created a curse and changed baseball forever.
The Red Sox sold Babe Ruth to the Yankees for $100,000 in January 1920. Owner Harry Frazee needed cash for Broadway productions and received a loan with Fenway Park as collateral. Ruth had just set the home run record with 29 in 1919. The deal triggered the Curse of the Bambino, dooming Boston to 86 years without a championship.
Ruth revolutionized baseball in New York, becoming the sport’s biggest star and transforming how the game was played. He hit 54 home runs in his first Yankees season, more than any entire American League team that year. The Yankees built their dynasty around Ruth, winning multiple championships while Boston languished in mediocrity. The trade remains the gold standard for lopsided deals that haunt franchises forever.
1964: Lou Brock for Ernie Broglio
The Cubs traded a future Hall of Famer for damaged goods.
The Cubs sent 24-year-old Lou Brock to the Cardinals on June 16, 1964, desperate for pitching help from 18-game winner Ernie Broglio. Chicago fans celebrated initially, believing they’d pulled off a heist by acquiring the established pitcher. Brock was hitting just .251 and seemed like a disappointment, making the trade look like smart baseball.
Brock immediately hit .348 for the Cardinals, leading them to the 1964 World Series championship over the heavily favored Yankees. He went on to collect 3,023 hits and 938 stolen bases, becoming baseball’s all-time steals leader at the time. Broglio won just seven more games before retiring in 1966 due to elbow problems the Cardinals knew about.
2016: Fernando Tatis Jr. for James Shields
White Sox gave away a generational talent for a washed veteran.
Chicago traded 17-year-old Tatis Jr. to the Padres for veteran pitcher James Shields in June 2016, before the teenager had played a professional game. The White Sox needed rotation help and didn’t view Tatis as untouchable among their prospects. Shields had been a reliable starter for years, and Tatis was far from contributing. The Padres had scouted Tatis extensively and targeted him specifically as the key piece in the deal.
Shields posted a disastrous 6.77 ERA in his first White Sox season and finished with a 5.31 ERA over three years. Tatis became one of baseball’s brightest young stars, winning two Silver Slugger awards by age 25 and signing a $340 million contract extension. The trade ranks among the worst in baseball history, with Chicago giving up a franchise cornerstone for essentially nothing.
2020: Mookie Betts to the Dodgers
The Red Sox repeated their curse-worthy mistake with another superstar.
Boston traded 27-year-old superstar Mookie Betts to Los Angeles in February 2020, just two years after he won MVP. The Red Sox wanted to shed salary and avoid paying Betts what he deserved in free agency. Betts had led Boston to the 2018 World Series championship and was entering his prime years.
Betts signed a 12-year, $365 million extension with the Dodgers and immediately led them to the 2020 World Series championship. He remained one of baseball’s elite players, making All-Star teams and winning another ring in 2024. The Red Sox haven’t reached those heights since trading him away, with only backup catcher Connor Wong remaining.
1971: Nolan Ryan to the Angels
The Mets traded a future legend for an aging veteran.
New York sent 24-year-old Nolan Ryan to California for shortstop Jim Fregosi in December 1971. The Mets needed infield help and viewed Ryan as expendable despite his overpowering fastball and obvious potential. Fregosi was a four-time All-Star whom the Mets hoped would stabilize their lineup for years to come.
Fregosi played just 146 games for the Mets over two disappointing seasons before being released. He hit .233 with minimal power, providing almost no value before his quick exit from New York. Ryan became one of the greatest pitchers in baseball history, throwing seven no-hitters and striking out over 5,700 batters.
1987: John Smoltz for Doyle Alexander
The Tigers traded a Hall of Famer for a brief playoff push.
Detroit sent 20-year-old John Smoltz to the Braves for veteran Doyle Alexander in August 1987. The Tigers were in a tight pennant race and needed immediate pitching help to push them over the top. Smoltz was just a minor league prospect at the time, making the trade seem reasonable for contenders.
Alexander led the league in losses two years later and retired shortly after, providing minimal long-term value. Smoltz became the first player in MLB history to record 200 wins and 150 saves during his career. He won the 1996 Cy Young Award, made eight All-Star teams, and dominated for over two decades in Atlanta.
2018: Robinson Cano and Edwin Diaz to the Mets
Seattle dumped bad contracts while New York paid the price.
The Mariners traded All-Star closer Edwin Diaz and veteran Robinson Cano to the Mets on December 3, 2018. Seattle wanted to rebuild and clear Cano’s massive contract off their books, even including elite closer Diaz. New York sent top prospects Jarred Kelenic and Justin Dunn to Seattle in the deal.
Cano struggled with injuries and ineffectiveness in New York before another suspension ended his Mets tenure. Diaz had ups and downs, never replicating his franchise-record 57-save 2018 season consistently. Kelenic became a solid major leaguer for Seattle, while the package helped the Mariners rebuild their system.
TL;DR
- The Babe Ruth sale to the Yankees in 1920 created an 86-year championship drought for Boston.
- Lou Brock became a Hall of Famer after the Cubs traded him for damaged pitcher Ernie Broglio.
- White Sox gave up Fernando Tatis Jr. before he played a game for underwhelming pitcher James Shields.
- The Red Sox repeated history by trading MVP Mookie Betts, who won championships with the Dodgers.
- Nolan Ryan became the strikeout king after the Mets traded him for aging shortstop Jim Fregosi.
- These trades show how one bad decision can haunt franchises for generations while building dynasties elsewhere.
Read More:
- How MLB umpires influence game physics through strike zone perception
- MLB defensive shifts transforming how the game is played
- Historic MLB rivalries that still define team culture today
This article was made with AI assistance and human editing.
