The Biggest Deals of All Time

Mike Carminati and I have been using Win Shares to reflect upon baseball’s rich history of trades and transactions. We’ve mostly analyzed and listed winners and losers of many of these deals, but today I’d like to ask a different question. Namely, what have been the biggest deals in major league history? Which deals involved the greatest swap of future major league talent?

For a trade, purchase or waiver deal to rank among the biggest in history, one or more of the players must have been in his prime, or about to hit his prime. As you look at these deals, you’ll see that they included some of baseball’s greatest players ever, all of whom were already stars at the time they were traded. That’s what turned them into huge deals — the trading team had to get value in return for the star. Some of the deals were even for both teams, others were among the most lopsided ever. Each one is a great story.

To rank these deals, I used Win Shares and Win Shares Above Bench (WSAB), our shorthand method of estimating how much better a player was than a typical bench player each year. WSAB helps separate the superstars from everyone else.


Four trades stand out as the biggest in major league history:

December 5th, 1984: The Yankees trade Stan Javier, Tim Birtsas, Jay Howell, Eric Plunk and Jose Rijo to the Oakland Athletics for Rickey Henderson, Bert Bradley, and cash.

This is the archetypal prospects-for-superstar-entering-free-agency trade; it set the standard for all future Carlos Beltran-like trades. In the fall of 1984, Rickey Henderson was about to enter his final arbitration year, and he was already making noises about wanting a huge contract from the A’s. Although Los Angeles and Baltimore expressed interest, the Yankees eventually pried Henderson from the A’s by giving up four of their top five prospects (ranked by Baseball America) at the time.

A total of 827 future Win Shares traded hands in this deal, which is the most of all time. Henderson went on to rack up 378 Win Shares during the rest of his career. However, the young Yankee players in this deal also had good careers:

Javier: 137 Win Shares
Rijo: 131 Win Shares
Plunk: 86 Win Shares
Howell: 82 Win Shares

The overall tab for this trade was 449 future Win Shares going to the A’s and 378 to the Yankees. When you consider that the A’s probably would not have signed Henderson after the 1985 season, this was certainly a good deal for them. For perspective, less than forty trades have included more than 449 future Win Shares in total.

However, measured in WSAB, more future value went to the Yankees in this deal, 205-153. Picking up Henderson was a coup for the Yanks. He was just 25 years old at the time and he’d already posted a phenomenal total of 157 Win Shares in his first six years. He was on his way to becoming one of the greatest players of all time. Here’s what Bill James said in the 1985 Abstract about this deal:

Did they get a fair price for Rickey Henderson? It’s kind of like if you’re an art collector and you have the Mona Lisa, what’s a fair price for it? The idea in building a championship team is to acquire players like Rickey Henderson. It’s a sad day when you have to give one away.

Bill’s lament anticipated many commentaries that have been written since that earlier, innocent time.

December 5th, 1990: Roberto Alomar and Joe Carter traded by the San Diego Padres to the Toronto Blue Jays for Fred McGriff and Tony Fernandez.

The Sporting News called it a “trade for the ages,” and they were right. Pat Gillick and Joe McIlvaine stunned the baseball world when they announced a trade of four fine young players, all in their prime. Carter was 30, Fernandez was 28, McGriff was 27, and Alomar was 22. The Blue Jays got the oldest and youngest players, and the Padres got the players in the middle. The new Padres had compiled 237 Win Shares at the time of the trade, while the new Blue Jays had compiled 186.

As James said at the time, “…I think if you computer-designed a trade, asking which teams could trade two stars each way without anybody gaining or losing much, you’d have a hard time coming up with a better balance.”

In terms of WSAB, this is the biggest trade of all time, the greatest exchange of premium talent. 358 WSAB traded hands in the Henderson deal, but Toronto and San Diego swapped a total of 395 future WSAB in this deal, and 814 total future Win Shares.

A Hardball Times Update
Goodbye for now.

Supposedly, Gillick made this deal to bust up the “clique-ridden” Blue Jays. They had finished second in the AL East in 1990 with an 86-76 record, and the theory was that clubhouse acrimony was holding them back from the championship. There is no arguing with the results — the Blue Jays proceeded to go on a sensational three-year run of AL East division championships. Alomar led the team in Win Shares two of those three years and Joe Carter hit one of the most famous World Series home runs in history.

Thanks to Alomar’s great career, the Blue Jays got the better of this trade 220 WSAB vs. 175, an outcome that was predicted by the Stats Baseball Scoreboard at the time. But I just like to remember this trade as the biggest total exchange of future superstar talent in history.

November 29, 1971: The Houston Astros traded Joe Morgan, Ed Armbrister, Jack Billingham, Cesar Geronimo, and Denis Menke to the Cincinnati Reds for Lee May, Tommy Helms, and Jimmy Stewart.

The third biggest Win Share trade in history (and fourth-largest WSAB trade) is also the sixth-most lopsided trade in history, according to Mike Carminati. Lee May had a very good career after being traded to Houston (127 WS and 46 WSAB), and Cesar Geronimo had some good years with the Reds (103/23). But it was Little Joe who made this deal huge (357/227 after being traded).

The Astros seemed determined to trade Morgan for some reason. According to that winter’s Sporting News:

Joe seems to be in somewhat the same situation as Rusty Staub before his trade in 1969 — he is something of a sore point with management in ways that are not readily apparent and have nothing to do with playing the game.

Staub had been dealt to the Expos in one of the more lopsided deals in baseball history. That Astro management team apparently had some personal issues with talented players.

Morgan was a 27-year-old second baseman with a huge array of skills. But Lee May was also one of the best power hitters in the major leagues at the time, having just finished third in NL home runs and fourth in Slugging Percentage. And May was only a year older than Morgan.

The Astros supposedly made this move to bolster their offense, which had scored only 585 runs in 1971. In 1972, they moved the fences in, added May and scored 708 runs, finishing second in the division. But the Reds, led by Morgan’s 39 Win Shares, turned into the Big Red Machine.

Morgan had an incredible run after being traded. His highest Win Share total with the Astros was 30, but in the six years after being traded to the Reds, he logged 39, 40, 37, 44, 37 and 30 Win Shares each year.

That run turned this deal into one of the biggest and most lopsided trades of all time.

April 12, 1916: Tris Speaker traded by the Boston Red Sox to the Cleveland Indians for Sam Jones, Fred Thomas, and $55,000.

The second-biggest trade in WSAB (but only seventh in total Win Shares), this deal was another financially driven one. Back in 1914 and 1915, competition with the Federal League for top players had forced Boston to raise Tris Speaker’s salary to $18,000. When the Federal League disbanded, the Sox wanted to decrease Speaker’s salary to the pre-Federal level of $9,000. Speaker, who led the AL in Win Shares in 1912 and 1914, said he’d rather sit. So Boston sent the 27-year-old Tris packing to Cleveland for Sad Sam Jones and third baseman Fred Thomas.

Cleveland won this deal thanks to the 365 Win Shares that Speaker would go on to collect (Speaker, Henderson and Morgan belong in the same class of superstar). But Sam Jones also had a fine career, racking up 238 Win Shares and 130 WSAB after the trade, which is what helps catapult this deal to Number Two in total WSAB exchanged. Considering their financial motivation, the Red Sox could have done worse. This is only the 68th most lopsided trade in history.

The Waiver King

May 4, 1936: Dixie Walker selected off waivers by the Chicago White Sox from the New York Yankees.
July 24, 1939: Dixie Walker selected off waivers by the Brooklyn Dodgers from the Detroit Tigers.

Dixie Walker was a wildly popular player in the 1940’s for Brooklyn, where they called him the “People’s Cherce.” Walker is also known for demanding a trade when Jackie Robinson first joined the Dodgers, though he later retracted his request. Still, Branch Rickey traded him a year later (for Preacher Roe and Billy Cox — one of the better trades in Dodger history).

But Dixie Walker should also be known as the best waiver pickup in history. In fact, Walker should be known as two of the top three waiver pickups ever, making him the Waiver King. When the White Sox and then the Dodgers selected him three years apart, he still had a fine career ahead of him (266 WS and 146 WSAB to go when the Sox picked him and 225/126 when the Dodgers picked him). The Dodgers were the ones smart enough to hang onto him.

Why was Walker waived so often? Well, it wasn’t because he was untalented. In fact, the Yankees had bought him from Greenville for a then-record $25,000 in 1930, and they reportedly considered him a successor to Babe Ruth. But Walker tore some shoulder muscles crashing into a fence and had only played one full season in the majors by the age of 25. When DiMaggio was ready for the majors, Walker was put on waivers. That’s right, Walker was considered a successor to Babe Ruth and replaced by Joe DiMaggio. Talk about name-dropping.

He had a solid year in 1937 for the Sox, but they traded him to Detroit for some reason, who then waived him a year and a half later as Walker continued to struggle with his shoulder. Brooklyn reaped the benefits of all those waivers as Walker eventually started to realize his talent in his late 20’s, and he compiled 200 Win Shares in eight seasons for them.

Players for Sale

The list of most Win Shares sold from one team to another is a different kind of list. It consists of players on teams whose owners wanted to turn their “owned” talent into cash for reasons of profit or control. Nap Lajoie, Eddie Collins and Rube Waddell were all sold to other teams, and those owners knew exactly what they were doing.

Of course, there were a few exceptions, such as Dazzy Vance. And one big one. When Babe Ruth was sold to the New York Yankees, he had 576 Win Shares left in him and 407 Win Shares Above Bench. In WSAB, Babe Ruth represented, all by himself, more future value than any other combination of players in any transaction in major league history. More than Henderson, Javier, Rijo and friends combined. More than Alomar, McGriff, Carter and Fernandez put together. More than Morgan, May and etc. More than Dixie Walker counted twice.

The Curse may be over, but the sale of Babe Ruth casts a long shadow over every other transaction in major league history. It was the biggest, most lopsided and most important transaction in the history of sports.

References & Resources
Mike and I have written a number of articles about major league transactions. We started with the transaction database from Retrosheet (God Bless Retrosheet) and added Bill James’s Win Shares to each one.

The information used here was obtained free of charge from and is copyrighted by Retrosheet. Interested parties may contact Retrosheet at 20 Sunset Rd., Newark, DE 19711.

Here are some of the previously published articles:

The Best and Worst Teams of the Trade
Smoltz for Alexander
The Most Lopsided Trades (Part One)
The Most Lopsided Trades (Part Two)
The Most Lopsided Trades, but only including years that the traded players played for each team
History of all Red Sox/Yankee transactions (Part One)
Red Sox/Yankees (Part Two)
An Intro to the History of Kansas City/Yankee trades

The Sporting News archives are available for a fee at the Paper of Record. SABR members get a discount. Old copies of Bill James’s Abstracts and the STATS Baseball Scoreboard are available in my son’s bedroom, because my wife won’t let me keep them in our room. I don’t understand women. I also found my copies of Total Baseball and Koppett’s Concise History of Major League Baseball useful.

WSAB (or Win Shares Above Baseline) is a measure of how much a player contributed beyond a typical bench player. There is a big difference between a player who contributes 20 Win Shares a year for two years and one who contributes 10 Win Shares a year for four. The first player is more valuable because bench players are easier to find.

WSAB is a makeshift metric, based loosely on some research I’ve been conducting at my baseballgraphs site. For position players, WSAB is each Win Share above ten in a year; for starting pitchers, it’s each Win Share above six, and for relief pitchers it’s each Win Share above five.

Dave Studeman was called a "national treasure" by Rob Neyer. Seriously. Follow his sporadic tweets @dastudes.

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