These two teams were extremely active dealing with each other in the first four decades of the century, their proclivity to trade with each other dried up in the Forties, when their rivalry is generally acknowledged to have begun in earnest.
# 1 Date: January 3, 1920
Trade: Yankees purchase Babe Ruth from the Red Sox.
May 6, 1930
This is the most lopsided transaction of all time.
# 2 Date: May 6, 1930
Trade: Red Sox trade Red Ruffing to Yanks for Cedric "Don't Call Me Fred" Durst and $50 K.
Another Hall-of-Famer acquired in his prime (age 25).
Date: December 15, 1920
# 3 Date: December 15, 1920
Trade: Red Sox trade Waite Hoyt, Harry Harper, Mike McNally, and Wally Schang to Yankees for Muddy Ruel, Del Pratt, Sammy Vick, and Hank Thormahlen..
Hoyt was another future Hall of Famer, acquired when he was just 21. Schang, Pratt, and Ruel were also productive players, favoring the Sox slightly in the non-Hoyt side of the trade.
#4 Date: January 30, 1923
Trade: Red Sox trade Herb Pennock to Yankees for Camp Skinner, Norm McMillan, George Murray, and $50 K.
Yet another future Hall-of-Famer, Pennock, this time acquired at age 29.
#5: Date: July 29, 1919
Trade: Red Sox trade Carl Mays to Yankees for Allan Russell, Bob McGraw, and $40 K.
Mays wasn't a Hall-of-Famer (at least he hasn't been elected yet), but he was close, and he sure looked like one on the Sox. Russell had some success with the Sox and Senators. He actually won more games in 1919 after the trade than Mays (10 to 9).
#6 Date: May 12, 1933
Trade: Red Sox purchase Billy Werber from Yankees.
The Sox finally take one, and it's Billy Werber?!? Werber was a pretty good third baseman for the Sox before the sent him to the A's after three seasons.
# 6 Date: March 22, 1972
Trade: Red Sox sent Sparky Lyle to Yankees for Danny Cater and a player to be named later (Mario Guerrero sent June 30).
# 7: Date: January 3, 1923
Trade: Red Sox sent George Pipgras and Harvey Hendrick to Yankees for Al DeVormer.
Pipgras was a 23-year-old prospect that would go on to win 24 games for the Yankees in 1928 and 57 over three years (1928-30). Hendrick, also a rookie, was a corner outfield-first base type who had some offense and very little defense. DeVormer was a 30-year-old backup catcher with just 127 ABs under his belt at the time. He split time behind the plate with Val Picinich in 1923 and then was, other than a cup of joe with the Giants in 1927, was through in the majors.
# 8 Date: July, 1902
Trade: Boston Somersets purchase Tom Hughes from Baltimore Orioles.
A second win for Boston and it comes when the Yankees were still in Baltimore.
Hughes won 20 games for Boston in 1903 and then was traded back to the Yankee franchise, now in New York and known as the Highlanders, for Jesse Tannehill, who won 21 and 22 games over the next two years for Boston. Hughes was 7-11 in part of a season with the Yanks and then was sent to Washington for Al Orth who won 27 games for the Highlanders in 1906.
# 9 Date: July 23, 1922
Trade: Yankees send Lefty O'Doul, Chick Fewster, Elmer Miller, Johnny Mitchell, and $50 K to the Boston Red Sox for Joe Dugan and Elmer (J.) Smith.
The Yankees give up too much to get two veterans? The trade drew a protest from then contending St. Louis, causing Commissioner Landis to change the rules to bar non-waiver trades after June 15.
O'Doul was still a young pitcher when the Yanks shipped him to the Sox. He would blow his arm out in Boston and then go back to the PCL to turn himself into a very good batting outfielder with the Giants, Phils, and Dodgers.
Smith stinks up the field in NY (.185 batting average), and survives only one more year with the Yankees (122 OPS+) and two more years in the majors. Dugan was the Yankee third baseman and leadoff hitter for many years. So even when the Red Sox "win" one, they don't benefit from it.
# 10: Date: June 18, 1904
Trade: Boston Pilgrims send Patsy Dougherty to the New York Highlanders for Bob Unglaub.
This was a trade that was highly criticized in Boston in its day. Some theorized that it was orchestrated to help the Highlanders compete with the Giants.
Dougherty played well for the Yankees until he got into a fistfight with manager Clark Griffith in 1906 and was waived. He then became part of the "Hitless Wonder" White Sox.
Unglaub was a weak-hitting first baseman, who started just one season in Boston. Six games after the trade he was hospitalized for blood poisoning.
Source by Mike Carminati