From 1923 to 1985, the Major League Baseball trading deadline was June 15. It was Barney Dreyfuss, owner of the Pittsburgh Pirates and now a member of the Baseball Hall of Fame, who suggested it to Commissioner Kenesaw Mountain Landis, based on a late-season trade the Yankees made that had helped them win a Pennant.
Since the 1986 Basic Agreement between the players and the team owners, the deadline has been a bit later, July 31, or August 1 if the preceding date falls on a Sunday. The move was recommended because teams have a better idea of what they'll need for the rest of the season after the All-Star Break than they would before.
We've seen Brian Cashman have the official role of general manager of the New York Yankees since the 1998 season. Since the death of George Steinbrenner in 2010, he has had pretty much full control from George's sons Hal and, until his own death in 2020, Hank. And, since the retirement of Derek Jeter in 2014, he has had to operate without players acquired by his predecessors Gene Michael and Bob Watson.
Which of these trades would Cashman have made, given his known preferences? These are listed in chronological order. And remember: These are trades. In some cases, there may have been cash involved, but each team received at least one player. So the 1920 purchase of Babe Ruth from the Boston Red Sox will not be mentioned. Nor will free agent signings like Reggie Jackson.
Top 10 Yankee Trades
1. July 30, 1919, with the Boston Red Sox.
Yankees get: Pitcher Carl Mays.
Yankees give: Pitchers Bob McGraw and Allen Russell, and $40,000.
Result: Mays wasn't a great teammate, but from 1916 to 1926 -- in Boston, New York and Cincinnati -- he was a great pitcher. In 1921, he went 27-9 to help the Yankees win their 1st Pennant. Had there been a Cy Young Award at the time, he would have won it easily. He was less key for the 1922 Pennant and the 1923 World Series win, and was then traded away -- and then won 20 for the Cincinnati Reds in 1924 and 19 in '26.
People point to the sale of Ruth as where the Red Sox were ruined and the Yankee Dynasty was made. That wasn't it. It was the trading of key pitchers to the Yankees that did it, as you'll see with these next 3. Well, 4, but the last of these was done after Harry Frazee sold the Red Sox in 1923 (and even after he died in 1929).
The consequences of this trade went far beyond the results on the field. This was the trade that split the American League. Every bit as much as the subsequent Black Sox Scandal, this trade helped create the office of the Commissioner of Baseball, and took a lot of power away from the League Presidents, especially AL President and founder Ban Johnson.
Would Cashman make this trade? No. McGraw and Russell were "prospects," and Mays wouldn't have been worth his view of risk.
2. December 15, 1920, with the Boston Red Sox.
Yankees get: Pitchers Waite Hoyt and Harry Harper, catcher Wally Schang and infielder Mike McNally.
Yankees give: 2nd baseman Del Pratt, catcher Herold "Muddy" Ruel, pitcher Hank Thormahlen and right fielder Sammy Vick.
Result: Pratt gave the Sox a .300 season, and Ruel later helped the Washington Senators win their 1st 2 Pennants, including 1924 when they edged the Yankees. But Hoyt became the 1st real Yankee ace since Jack Chesbro in the founding Highlanders era, helping the Yankees win their 1st 6 Pennants. Schang was the catcher on the 1st 3 of those.
McNally was an afterthought. So was Harper, but he went on to have an interesting political career. As a Republican in New Jersey, he ran successfully for Sheriff of Bergen County, and unsuccessfully for the State Assembly and Congress. He also served in the Cabinets of Governors Walter Edge and Alfred E. Driscoll.
Would Cashman make this trade? Yes. Before the trade, Hoyt was a mere 10-12 for his career, with a 3.85 ERA. And I can easily see him giving up on Pratt and Ruel. And Schang was 31 and, by the standards of the time, had some power. But he was a switch-hitter, and Cashman might not have gone for that.
3. December 20, 1921, with the Boston Red Sox.
Yankees get: Pitchers "Bullet" Joe Bush and "Sad" Sam Jones, and shortstop Everett Scott.
Yankees give: Shortstop Roger Peckinpaugh, and pitcher Harry "Rip" Collins, Bill Piercy and Jack Quinn.
Result: Peckinpaugh, like Ruel, helped the Washington Senators win their 1st 2 Pennants. Quinn would pitch until he was 50, helping Connie Mack establish the next Philadelphia Athletics dynasty in the late 1920s. And Collins would be the starting catcher on the St. Louis Cardinals' 1931 World Series winners.
Even with all of that, the Yankees won this trade going away. They got 2 fantastic pitchers to go along with Hoyt and Bob Shawkey, the latter a key purchase from Mack in 1915 rather than a trade acquisition. Bush went 26-7 in 1922, and would have been an easy choice for the Cy Young Award. He went 19-15 in 1923, to help the Yankees win the World Series for the 1st time.
Jones was just 13-13 in 1922, but went 21-8 in 1923, and would have won that year's Cy Young Award. Scott was also key, and should be remembered as a solid fielder and a good contact hitter, not just as the man who held the record for most consecutive games played prior to Lou Gehrig, 1,308.
Would Cashman make this trade? Yes. Bush was 90-94 from 1915 to 1921. Jones was 23-16 in 1921, but 23-36 in the 2 seasons before that. And Scott would have seemed like a throw-in.
4. January 30, 1923, with the Boston Red Sox.
Yankees get: Pitcher Herb Pennock.
Yankees give: Infielder Norm McMillan, pitcher George "Smiler" Murray, outfielder Elisha "Camp" Skinner and $50,000.
Result: The Yankees got 5 Pennants and 4 World Series wins. The Sox probably got more use out of the cash than the players.
Would Cashman make this trade? Yes. He would have given up next to nothing, and he got a lefthanded pitcher who had won a Pennant with Mack's Athletics (where he was a teammate of Schang and Shawkey) and 2 with the Sox, and was 32-21 in 1919 and '20, but was just 23-31 with an ERA over 4 in '21 and '22, and had injuries before. He was comparable then to Corey Kluber and Jameson Taillon now.
5. May 6, 1930, with the Boston Red Sox.
Yankees get: Pitcher Charles "Red" Ruffing.
Yankees give: Outfielder Cedric Durst and $50,000.
Result: Durst was retired by the end of the season. Ruffing won 231 games for the Yankees, still the most of any righthanded pitcher. (Only Whitey Ford has more among lefthanders, with 236.) He and Vernon "Lefty" Gomez helped the Yankees win the 1932, '36, '37, '38, '39 and '41 World Series. Ruffing would have won the Cy Young Award in 1938 and '39.
Would Cashman make this trade? Yes. In losing Durst, he would have given up next to nothing. In Ruffing, he would have gained a pitcher who was 39-96 for Boston, but would have had a chance to do great things for a team with hitters like Babe Ruth and Lou Gehrig behind him.
6. October 11, 1946, with the Cleveland Indians.
Yankees get: Pitcher Allie Reynolds.
Yankees give: 2nd baseman Joe Gordon.
Result: Finally, not one where the Yankees fleeced the Red Sox. This was one of the best trades in baseball history, one that won at least 1 World Series for both teams. Gordon, the 1942 AL Most Valuable Player, secured his (posthumously-elected) Hall of Fame status by helping the Indians win the 1948 World Series. But the Yankees got George "Snuffy" Stirnweiss in a separate trade, and then had Jerry Coleman, Billy Martin and Bobby Richardson at the keystone sack for the next 15 years.
The Indians needed a veteran infield presence like Gordon, and were willing to trade any pitcher except the future Hall-of-Famer Bob Feller. Yankee GM Larry MacPhail asked Joe DiMaggio which one he should take. The Yankee Clipper said, "Take Reynolds. I'm a fastball hitter, but he can buzz his hard one by me any time he has a mind to." In other words, "He's really good, so even if he does nothing for us, at least he won't be doing anything to us."
That fastball, and his Cherokee heritage, got Reynolds a nickname that applied to Native Americans and a famous train of the time: The "Superchief." In a rotation that already included Vic Raschi, the "Sprinfield Rifle," the Yankees won the 1947 World Series. In 1948, the Yankees obtained Eddie Lopat, a lefthander specializing in off-speed pitches, known as "the Junkman."
And with new manager Charles "Casey" Stengel coming in for the 1949 season, and pitching the speedy righthander Reynolds followed by the junkballing lefty Lopat, followed by the speeding righthander Raschi, the Yankees had a very tough combination that won the next 5 World Series: 1949, '50, '51, '52 and '53 -- each time with a different 4th starter. So this trade helped the Yankees get 6 titles.
Reynolds only won 20 games once, in 1952, but that was partly because Stengel also frequently used him as a reliever. Had he come along 30 years later, he might have been a big blazing righthanded closer in the mold of Goose Gossage. He hurt his back in 1954, but still managed to go 13-4 at age 37, then retired: Having invested in oil wells in Oklahoma, he could afford to play for the love of the game, and then walk away.
Would Cashman make this trade? Yes. Trading Gordon would have taken a big salary off the books, and Reynolds was just 51-47 with Cleveland, albeit with a 3.31 ERA. In Cashman's mind, it would have been an easy choice. In MacPhail's mind, and in a baseball historian's mind, it actually was.
7. December 11, 1959, with the Kansas City Athletics.
Yankees get: Right fielder Roger Maris, infielder Joe DeMaestri and 1st baseman Kent Hadley.
Yankees give: Right fielder Hank Bauer, pitcher Don Larsen, outfielder Norm Siebern, and 1st baseman Marv Throneberry.
Result: This was one of several trades the Yankees made with the A's from their 1955 arrival in Kansas City until 1960, when team owner Arnold Johnson died and the team was bought by Charles O. Finley, who stopped the original Yankee "shuttle." Anytime the A's got a player the Yankees thought was good, the Yankees would send the A's a veteran player they didn't need anymore, and get the prospect. Some players would go back and forth between the teams, including pitcher Ralph Terry and outfielder Bob Cerv.
It got to the point where people, remembering that the Kansas City Blues had been the Yankees' top farm team before the A's left Philadelphia, said that Kansas City was still a Yankee farm team.
Bauer helped the Yankees win 9 Pennants in 11 years, played 2 more years for the A's, and retired. Siebern became an All-Star for the A's, and then again for the Baltimore Orioles, where Bauer was his manager. (Bauer managed the Orioles to their 1st Pennant and World Series win in 1966, but, by then, Siebern was gone.) Larsen, the man who pitched a perfect game in the 1956 World Series got to the San Francisco Giants, and helped them win the 1962 National League Pennant, even pitching against the Yankees in the World Series.
Throneberry was the Yankees' top prospect. But he didn't do much in Kansas City, and then not much in Baltimore. Early in the 1962 season, the Orioles traded him to the New York Mets. While the short right field fence at the Polo Grounds allowed him to hit 17 home runs, showing what used to be known as "oafish clout," his fielding at 1st base was legendarily bad, on the same level (if not as a slugger) with that of Dick "Dr. Strangeglove" Stuart.
Hadley played the 1960 season with the Yankees, got sent down to the minors, and then played a few seasons in Japan. DeMaestri was a decent reserve infielder on the early 1960s Pennant winners. But those 5 Pennants, including the 1961 and '62 World Series, wouldn't have been won without Maris.
He became the AL MVP in 1960. He won the MVP again the next year, setting a new single-season home run record, the famous "61 in '61," despite seemingly everybody hoping that he wouldn't break Ruth's record of 60 in 1927, and that teammate Mickey Mantle would. In addition, Maris might have been the best-fielding right fielder in Yankee history. Perhaps no player in Yankee history was treated worse, by fans, by team management, and by the sportswriters. And few deserved it less. He didn't have Hall of Fame career statistics, but he was a Hall of Fame person.
Would Cashman make this trade? Never in a million years. Maris was a lefty, and Throneberry was the crown jewel of the Yankee farm system, having already made a bit of a contribution to their 1958 World Championship season. Who knew his name would become a byword for baseball ineptitude?
Cashman would have let Throneberry become the successor to Bill "Moose" Skowron at 1st base, and moved Joe Pepitone to the outfield. Or, maybe he would have let Pepitone succeed Skowron, as actually happened, and, seeing how bad Throneberry was at 1st, moved him to the outfield.
8. March 22, 1972, with the Boston Red Sox. Here we go again.
Yankees get: Pitcher Albert "Sparky" Lyle.
Yankees give: 1st baseman Danny Cater and shortstop Mario Guerrero.
Result: Guerrero was a backup, basically a throw-in. The Red Sox' reasoning was that Cater hit well at Fenway Park, so why not let him hit there 81 times a year? They didn't get it: The reason he hit well at Fenway was that the Red Sox had weak pitching. Now, he wasn't facing that pitching. He last played in 1975. Lyle was a rookie on Boston's 1967 "Impossible Dream" Pennant season, but had been inconsistent. He was 27, and it looked to them like he wasn't going to pan out.
In his 1st season with the Yankees, Sparky went 9-5, and set a major league record with 35 saves. (That record was broken by John Hiller of the Detroit Tigers the next season.) Sparky led the AL in saves again in 1976, and in 1977 went 13-5 with 26 saves, becoming the 1st AL reliever to win the Cy Young Award.
Would Cashman make this trade? Not a chance. Giving up Cater, a player who hit well at Fenway, would have been anathema to him.
9. December 11, 1975, with the California Angels.
Yankees get: Center fielder Mickey Rivers and pitcher Ed Figueroa.
Yankees give: Right fielder Bobby Bonds.
Result: The honorable mentions I could give for the early George Steinbrenner years are staggering. On the same day as this trade, the Yankees sent pitcher George "Doc" Medich to the Pittsburgh Pirates for 2nd baseman Willie Randolph and pitchers Ken Brett and Dock Ellis. (Unlike Medich, "Dock" was his actual birth name.)
Early in the 1977 season, the Yankees traded Ellis, outfielder Larry Murray and infielder Marty Perez to the Oakland Athletics for pitcher Mike Torrez. Right before that season, they sent outfielder Oscar Gamble, pitcher LaMarr Hoyt, pitcher Bob Polinsky and $250,000 to the Chicago White Sox for shortstop Russell "Bucky" Dent.
Just before George bought the team, but after he had begun negotiations, so he probably gave his okay to it, the Yankees sent catcher John Ellis, 3rd baseman Jerry Kenney, and outfielders Charlie Spikes and Rusty Torres to Cleveland for 3rd baseman Graig Nettles and catcher Jerry Moses. A year after that, the Yankees sent pitcher Lindy McDaniel to the Kansas City Royals for outfielder Lou Piniella.
While the White Sox got a Cy Young season out of Hoyt, and McDaniel helped make the Royal pitching staff one of the best in baseball (more due to his teaching than to his pitching, as he was near the end of his career), each and every one of these trades was genius for Yankee GM Gabe Paul (especially since he was the Indian GM for the Nettles trade, knowing he was going to the Yankees, in what was clearly a conflict of interest).
Specifically about the Rivers & Figueroa for Bonds trade: With the San Francisco Giants, the team for whom his son Barry would later become a legend, Bobby Bonds was one of the best players in the game, a rare combination of good power and great speed. Steinbrenner couldn't resist, and sent the beloved Bobby Murcer to Candlestick Park to get him. (Murcer would be reacquired in 1979.)
Bonds was a classic Brian Cashman player: Batted righthanded, had a lot of power, struck out too much (at the time, he had seasons of 189 and 187 strikeouts, then MLB records), and took risky chances on the bases that hurt often enough to make people think the times it paid off weren't worth it. He had good stats for the Yankees in 1975, but didn't really fit in. It wasn't a question of should he be traded, but for what.
Figueroa joined a rotation that already had the 1st big free agent signing, Jim "Catfish" Hunter, and Ellis. It would soon have prospect Ron Guidry. Figgy was key for the 1976 Pennant and the 1977 World Series. In 1978, he became the 1st Puerto Rican-born pitcher to win 20 games in a season. He remains the only one.
At the time of the trade, the Yankees were managed by Billy Martin. Rivers was Billy's kind of player: A contact hitter with a little power, great speed, smarter on the bases than Bonds, and a good fielder. He was a little flaky, but he was the ideal leadoff hitter for the late 1970s Yankees.
Would Cashman make this trade? No way! He wouldn't give up a speedy righthanded slugger like Bonds for a lefty contact hitter like Rivers. He might have tried to acquire Figueroa, but not at the cost of Bonds.
10. November 3, 1992, with the Cincinnati Reds.
Yankees get: Right fielder Paul O'Neill.
Yankees give: Center fielder Roberto Kelly.
Result: At first, I thought this was a great trade for both teams. O'Neill had been part of the Reds' 1990 World Series win, managed by former Yankee Piniella. And he reminded me of a lefty version of Sweet Lou: An intense player, good glove, not much speed but a hustler who knew when the extra base could be taken, and had some power. With the short right-field fence at Yankee Stadium, he would hit more home runs. And while he was already 29 years old, the switch from Riverfront Stadium's artificial turf to real grass could only help him.
With the rise of Bernie Williams, the Yankees could afford to give up Kelly, already an All-Star. A righthanded hitter, he would have been better off in the hitting-neutral Riverfront than in Yankee Stadium, with its left and center "Death Valley." And he had good speed, so the turf would help him as both a runner and a fielder.
At first, it looked like my prediction would come true: Kelly was named to the NL All-Star Team in 1993. But injuries struck him, and he was never the same player. Interestingly, he became a coach with the Giants, and, along with former Yankee reliever Dave Righetti, won 3 World Series rings in that capacity.
O'Neill was exactly what the Yankees needed: As Steinbrenner called him, a "warrior."
Would Cashman make this trade? Fugeddabouddit! Kelly may have been only a year and a half younger than O'Neill, but Cashman would still have seen him as a "prospect," and a strong righthanded-hitting one at that.
There were a few honorable mention trades in the 1990s. During the 1995 season, the Yankees sent pitcher Marty Janzen and 2 minor leaguers who never made it to the Toronto Blue Jays for pitcher David Cone. After the 1995 season, the Yankees sent pitcher Sterling Hitchcock and 3rd baseman Russ Davis to the Seattle Mariners for 1st baseman Tino Martinez and pitchers Jeff Nelson and Jim Mecir.
In 1998, the Yankees sent pitcher Kenny Rogers to the A's for 3rd baseman Scott Brosius. In the middle of the 2000 season, the Yankees sent left fielder Ricky Ledee and pitchers Jake Westbrook and Zach Day to the Indians for outfielder David Justice.
And then, on February 15, 2004, the Yankees sent infielder Alfonso Soriano to the Texas Rangers for shortstop Alex Rodriguez. Turning A-Rod into a 3rd baseman, that trade took until November 4, 2009 to pan out. Clearly, that was not one of the Top 10 trades in Yankee history.
That there hasn't been a trade capable of knocking any of these Top 10 out since 1992 is a black mark on Brian Cashman's record. Indeed, if I made a list of the Top 10 Worst Yankee Trades, at least 2 of his would be on it, maybe more.
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