The Boston Red Sox are not very good at trading with the New York Yankees

The Red Sox and Yankees have made some trades throughout the years that could make any Red Sox fan cry in their clam chowder
New York Yankees v Boston Red Sox - Game One
New York Yankees v Boston Red Sox - Game One / Winslow Townson/GettyImages

The Boston Red Sox and New York Yankees, even though they are division rivals, have made trades with each other. Contrary to popular belief, they are not averse to making a major trade. The Alex Verdugo trade is an example. History, however, has shown us the Red Sox are not very good at trading with The Evil Empire and the Yankees always seem to come out on top.

Looking back at Boston Red Sox-New York Yankees trades

It didn’t start with Babe Ruth … oh no! They literally traded the pitcher who had the lowest single season ERA in MLB history (Dutch Leonard 0.96 in 1914) to the Yankees. Along with Ernie Shore, they dealt two really good pitchers, and got next to nothing. In July of 1919, they dealt Carl Mays, who was a back-to-back 20 game winner. Mays had 26 and 27 wins for the Yankees in 1920 and 1921, but also was infamous of the bean ball that killed Cleveland shortstop Ray Chapman. In return, they got a pair of pitchers, including Allen Russell, who won 10 games twice and another that didn’t win a single game for them. Yikes.

The bleeding continued in the ‘20s when they sent three pitchers who were mainstays in the Yankee rotations in their World Series titles: Waite Hoyt, a Hall of Famer, Bullet Joe Bush, and Sad Sam Jones. Jack Quinn was the only player they got anything of value ... if you consider losing records value.

Lefty O’Doul did come to the Red Sox in 1922, but only had 35 at-bats with them. He goes on to hit .398 and .383 with the Phillies years later and wins two batting titles. Even if they did get quality, they squandered it.

They even dealt Ken Williams, the first 30-30 player in history to the Yankees, but fortunately, he was already 40 and his career was over. Score one for the Sox I guess?

Decades later, the Yankees returned the favor and deal Elston Howard, a 12-time All Star way past his prime to the Sox. His first year, he hit .147.

Then, in 1972, the Sox dealt future Hall of Fame and Cy Young Award pitcher Sparky Lyle. Ugh! You can almost excuse the bad trades in the ‘20s because of the money issues. In 1972, however, that wasn’t the case. They blew it on this one.

Recent history shows a 2014 trade for 2013 World Series hero Stephen Drew being sent for Kelly Johnson, who goes on to play a total of 10 games for the Sox while Drew hits 17 homers for the Yankees.

The only trade I could find where the Sox did come out on top happened on March 28, 1986. The Sox grabbed Don Baylor straight up for Mike Easler. Baylor was instrumental in getting the Sox to the brink of a World Series championship while hitting 31 home runs and posting 94 RBI.  Easler did hit .302 for the Yankees, but he was at the end of his career.

Looking back at the history of Red Sox-Yankees trades, I think if any Red Sox GM sees the area code of the Bronx on their phone, they should send it to voicemail.