Major League Baseball was founded way back in 1904 so coming up with a list of the best MLB trades ever is daunting.
Baseball has been a trading sport more than any of the other Big 4 American sports, mainly due to the value of acquiring prospects for star players. In most of the trades on this list, there is a clear winner and a clear loser, with the No. 1 pick being widely considered the greatest piece of business in the history of American sport.
Top 10 best MLB trades of all-time
Going all the way back to the beginning, the first openly all-professional baseball team was the Cincinnati Red Stockings. This team was founded in 1869 and since then teams have always looked to find ways of contracting the best players available.
The most successful MLB trades help out both teams, either at that time or in the future, but not every deal will work out that way. Here are the biggest trades of all time.
Alex Rodriguez to Yankees
This deal looked for months like it would be A-Rod to the Boston Red Sox from the Texas Rangers in 2004.
This required Rodriguez to take a wage cut, however, and the MLB Players Association nixed the deal. The Rangers needed to move Rodriguez and the New York Yankees stepped in.
Sending Alfonso Soriano to Texas, this move paired Rodriguez and Derek Jeter in the same infield as the Yankees boasted star power and celebrity throughout the team. The Red Sox did get the last laugh, however, winning their first World Series title in 86 years at the end of the 2004 season and beating the Yankees in the playoffs to get there.
Ryne Sandberg to Cubs
This three-player trade in 1982 saw Ryne Sandberg and Larry Bowa traded from the Philadelphia Phillies to the Chicago Cubs for Ivan DeJesus. Bowa and DeJesus went on to do little to nothing for their new clubs, while Sandberg, who was traded because he was written off as a career utility infielder by the Phillies’ staff, went on to greatness.
His 282 home runs on retirement were the most ever by a second baseman and he batted .285 for his career. It was defensively where Sandberg starred, however, winning nine Gold Gloves and making his way into the Hall of Fame.
Jason Varitek and Derek Lowe to Red Sox
This is one of the best MLB trades of all-time because of what the acquisitions of Varitek and Lowe meant to the Boston Red Sox over time. Neither player was ever the main guy on the team, but both were massive in helping the Red Sox end their curse and win the World Series in 2004.
Boston gave up Heathcliff Slocumb to the Seattle Mariners on the other side of this trade and it would have taken a baseball visionary at the time to predict the impact that the pair of players coming into Boston would have on the team leading into the 2000s.
Jose Bautista to Blue Jays
This is is one of the biggest baseball trades of all time and one many view as the greatest steal in MLB this century.
Jose Bautista was seen as nothing more than a role player with the Pittsburgh Pirates and in 2008 the Toronto Blue Jays stepped in and acquired a player who was playing Triple-A baseball for “a player to be named later”. That player was Robinson Diaz who played just 43 games for the Pirates.
Bautista became a six-time All-Star, led the majors in home runs in 2010 and 2011, and was one of the most feared sluggers in the league for the best part of a decade.
Frank Robinson to Orioles
This is a classic example of a general manager getting it wrong. Frank Robinson was a monster for the Cincinnati Reds where he hit 324 home runs and hit .303 over 10 seasons.
General Manager Bill DeWitt, however, thought that Robinson was at his peak and traded him to the Baltimore Orioles at the end of the 1965 season. He acquired three players in return, but the centerpiece was pitcher Milt Pappas who had a 4.04 ERA in two and a half years in Cincinnati.
Robinson hit an additional 179 home runs for the Orioles, winning the Triple Crown in 1966 and leading his new team to a World Series win.
John Smoltz to Braves
The counterweight in this deal was Doyle Alexander to the Detroit Tigers but it is Smoltz to the Atlanta Braves that has this on the list.
Smoltz was part of a Braves pitching rotation in the late 80s and early 90s that was the envy of the league. The only player ever to have more than 200 wins and more than 150 saves in the major leagues, Smoltz went from starter to closer seamlessly at the end of his career. Alexander, as a side note, was traded seven times throughout his career.
Jeff Bagwell to Astros
The Boston Red Sox aren’t historically great at this trade thing. In 1990, and looking for a veteran relief pitcher for the stretch run, they traded hot prospect Jeff Bagwell to the Houston Astros for Larry Anderson. Anderson had a respectable 1.23 ERA in 15 appearances for the Red Sox before leaving as a free agent at the end of the season.
Bagwell continued to develop in Houston and finished his Hall of Fame career with 449 home runs and a batting average of .297. He is widely regarded as one of the best first basemen of all time and for the Astros at least, this is one of the most successful MLB trades of all time.
Roger Clemens to Yankees
This was a weird one. Clemens was showing no signs of age as he won his second consecutive Cy Young award in 1998 with the Toronto Blue Jays despite being in his mid-30s.
A trade clause was invoked, but the New York Yankees refused to give up any of their best prospects for a player nearing the end of his career. The deal looked to be off, but suddenly it happened with the Yankees giving up only veteran David Wells and some low-level prospects. Clemens was a massive part of the Yankees’ winning the World Series in both 1999 and 2000.
Lou Brock to Cardinals
The only thing worse than a bad trade is a bad trade where your bitter division rival comes out on top. In June 1964, the Chicago Cubs made a deal that sent three players in either direction.
One of those players was a 25-year-old outfielder with excellent speed who had hit .257 with 20 home runs and 50 steals for the Cubs.
That player was Lou Brock, who would go on to set single-season and all-time records for stolen bases at the time.
He was a first-ballot Hall of Famer in 1985, the 14th ever player with 3,000 hits, and an absolute monster in the World Series where he hit .391 with four homers and 14 steals across three series. The key piece for the Cubs was pitcher Ernie Broglio who went 7-19 with a 4.50 ERA over two and a half seasons in Chicago.
Babe Ruth to Yankees
When looking at the greatest MLB trades of all time there is a clear number one.
The trade of Babe Ruth from the New York Yankees to the Boston Red Sox is the greatest trade of all time in any sport.
Ruth cost the Yankees $100,000 at the time, which is about $1.5 million in 2021 money.
The Yankees went on to win four World Series titles with Ruth in their lineup. The Red Sox did not win another championship for 86 long, and often seemingly cursed, years. Given the iconic status and celebrity that Ruth enjoyed with the Yankees, this is easily the best MLB trade in history.
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