KISSIMMEE, FL - MARCH 6:  First Baseman Jeff Bagwell #5 of the Houston Astros smiles at the plate against the Detroit Tigers during the spring training game at the Osceola County Stadium in Kissimmee, Florida on March 6, 2002.  (Photo by  Andy Lyons /Getty Images)

The Red Sox are undoubtedly ranked #1 in ‘worst trades of all time’ with the sale of Babe Ruth to the New York Yankees. It was the beginning of the most storied ‘curse’ in sports history, although at the time, the deal was not viewed as a bad thing for Boston.

Ruth was a star in 1920 when Red Sox owner Harry Frazee sold him to the Yankees for $100,000. Ruth was a major draw for the team attendance-wise, but questions began to surface about the long-term plans and longevity of Ruth in Boston.

Ruth, known for his outlandishly bad behavior, began to be viewed as a problem for the team’s owner and Frazee felt that getting rid of Ruth and using the cash to load up on cheaper, younger players would be a larger benefit to the organization. Frazee’s decision turned out to be a mistake that haunted the franchise for nearly a century.

But as we promised last week, we will not devote a whole story to Ruth, Frazee and the curse of the Bambino.

The Boston Red Sox have been fortunate in the sense that they have not have had many notably bad trades in the modern era. The most worst trades in team history
(Outside of the Ruth deal) all fall in the earlier part of the 20th century. Tris Speaker was unexpectedly dealt to the Cleveland Indians in 1916 for Sam Jones, Fred Thomas and cash.

Red Ruffing was dealt in 1930, marking the second elite pitcher the Red Sox sent to the Yankees in a decade. Ruffing was brought up to the Majors too quickly and struggled in his first few years as a Red Sox. The team became frustrated with their prospect and that opened the door for New York to swoop in and snatch Ruffing away. Ruffing went on to become a stalwart of the Yankees rotation in the thirties and eventually found his way into the Baseball Hall of Fame in 1967.

The Red Sox have certainly been attached to some bad deals, but the all seemed to have happened nearly 100 years ago. All accept the one that forever lives in infamy by way of Red Sox GM Lou Gorman.

“Who knew?”

On August 31st, 1990, the Red Sox traded an overlooked prospect named Jeff Bagwell to the Houston Astros for relief pitcher Larry Andersen (overlooked only by Gorman). Andersen was a rented arm for the Sox who were trying to solidify their bullpen for the 1990 playoffs. Bagwell was just a 22-year old farmhand who hit .333 with 34 doubles and 74 walks. Teams had inquired earlier in the season about Bagwell, but Gorman would not trade him until the temptation of Andersen arose.

In today’s baseball, you would probably never see a prospect dealt for a middle reliever as the position is just too volatile to put a large investment on. When Gorman traded Bagwell, Peter Gammons went on “Baseball Tonight” and said the Red Sox had just dealt away a future batting champion.

Andersen was good for the Sox in the regular season and helped the team win the AL East, but in the ALCS, he was terrible.

In three postseason appearances for the Red Sox, Andersen walked three batters, gave up three hits, two earned runs and took a loss in the four-game sweep at the hands of the Oakland Athletics. (Side note: Did you know the Red Sox only scored four runs in that four game sweep?)

Andersen was a free agent following the 1990 season and the Red Sox in their desperate attempt to win a World Series for Jean Yawkey, ending up letting Bagwell go with nothing to show for it. Bagwell went on to become a prolific power hitter for the Astros, clubbing 449 HRs and 448 doubles and claiming an NL MVP in his 15-year career. He finished as a .297 hitter and remains the biggest modern-era blunder in Red Sox history.

At least it wasn’t as bad as the Orioles…