Beware the Lopsided Trade

A review of Traded: Inside the Most Lopsided Trades in Baseball History and interview with author Doug Decatur

(cue the music from Jaws)

It is that time of the season where fans are clamoring for trades and GMs and media insiders look and feel as if their cell phones have been surgically attached to their ears. The trading deadline of July 31 at 4 pm is filled with excitement, yet fraught with peril.

The risks involved with a trade are often not apparent to the casual fan or even the educated fan because of the long-term ramifications of acquiring an established star for prospects that most of us have never seen play and in many cases never heard of until the trade has been made and then we learn how talented this player might be.

Trades, for the most part, can really only be judged in retrospect and one tool you might want to have on your bookshelf to help with analysis is Traded: Inside the Most Lopsided Trades in Baseball History, by Doug Decatur and published by ACTA Sports. Decatur is a former statistical consultant for the Reds, Brewers, Cubs and Astros, and using the Win Shares stat developed by Bill James, he has produced an accountant’s type view of the best and worst trades in baseball history.

Doug took some time with me to answer my Nine Questions and it is good stuff, really interesting. But first, a little background about the book.

Each franchise has its own section, organized by how the teams rank in making the best lopsided deals (the Cleveland Indians rank first all-time). The

Shibe Park, home of the Philadelphia Athletics

rankings are historical in nature, which really makes them meaningless. For example, according to Decatur, the Yankees and the Red Sox tied for the most lopsided bad trades in the 20th century with 21. Interesting but how many different ownerships and general managers changed positions during that time and really does the 1918 trade of and $60,000 to the Philadelphia Athletics for Bullet Joe Bush, Wally Schang and Amos Strunk, which is ranked as the Red Sox best trade of all-time, have any value in evaluating the Sox today?

While the rankings are interesting, it also makes finding anything very difficult within the book. As a member of the ACTA Sports family of authors I can say with pride that their books’ content is, almost without fail outstanding, but many of their books like this one are poorly organized (there is no index to look up a player or a team) and the design could only kindly be described as 20th Century Desktop Publishing.

To his credit, the research by Decatur was exhaustive and just to have a listing of deals for each club makes this a useful reference. But the book is just focused on Win Shares as a measure for the success of a trade, and there is much more to be taken into consideration. One of the problems with statistical analyses like this is that they leave out the human element. For example, there is no mention (at least that I could find) of the deal that brought Orlando Cabrera to Boston in 2004 and sent the grumbling Nomar Garciaparra out of town. You would be hard pressed to find anyone who would not regard the July 31, 2004 four-team trade sent Cabrera from the Montreal Expos to the Red Sox and Boston sending Nomar Garciaparra and Matt Murton to the Chicago Cubs, the Minnesota Twins sending Doug Mientkiewicz to the Boston Red Sox, the Cubs sending Justin Jones (minors) to the Minnesota Twins, and Francis Beltran, Alex Gonzalez and Brendan Harris to the Montreal Expos, as anything but lopsided and enabling the Sox to break the Curse.

Ideally, Decatur should be paired with another writer who takes Decatur’s expertise and brings you the story above, beneath, over and under a trade and then you will have a book as captivating as Moneyball.

Doug Decatur really knows his stuff and he took some time out of his busy schedule (definitely check out his contribution to, Five deadly sins of deadline deals) to answer nine questions from yours truly; the man is knowledgeable and interesting.

Nine Questions with: Doug Decatur

1. Doug, define “Lopsided” for us and how it’s determined.

The short version: Any trade in which the difference between the total future win shares acquired versus the total future win shares traded is 111 or more.

So eliminate all the other variables such as: future transactions; pennants won; other players on the team at that position, etc. It is simply the “water in the well” theory. Three win shares = one win. The more win shares a team has, then the more games a team wins and the more game a team wins, the more championships they usually win.

Now if you are looking for a definition of win shares. Win Shares is a way to relate a player’s individual statistics to the number of wins he contributed to his team. As a single number, Win Shares allows us to easily compare the accomplishments of each player and to compare players across positions. A team is credited with three Win Shares for each win (100 victories in a season equals 300 win shares to be divide among the team members), and the quality of the team does not affect an individual player’s Win Shares. A great player on a bad team will rate just as well as a great player on a good team. So for every three Win Shares a player earns, he had directly contributed one win to a team’s season record.

2. Talk a little about the Orioles/Astros deal that you call the most lopsided deal ever.

In 1991, the Astros traded Glen Davis to the Orioles for Steve Finley, Curt Schilling and Pete Harnisch.

Three things made this a lop-sided trade: (1) all three “prospects” in this deals had great careers; (2) Finley and Schilling also had extremely long careers; and (3) Glen Davis’ career was curtailed by injuries shortly after the trade. Note: research has shown that slow moving sluggers have relatively short careers. Thus, injury or no injury to Davis, the trade to acquire Davis was not a high percentage deal.

As a result of little or no policing of steroid use by major league baseball, questions always arise when players are able to maintain a high performance into their late thirties. In the case of Curt Schilling, Schilling has been very outspoken against steroid use and has even gone so far as to state that players such as Roger Clemens should have to relinquish their awards and players such as Jose Canseco should have their “statistics erased”. Thus, it is a pretty safe bet that Schilling did not use steroids. However, Steve Finley’s career, fair or unfair, has the look of a smoking gun. At age 35, Finley had his career best slugging percentage and then at age 38, Finley became the oldest player to lead the league in triples. Schilling (3) and Finley (1) would combine to win four World Championships during their careers. Unfortunately for the Astros, the World Championships came for other clubs after these two players left the Astros.

By the way, the #2 most lopsided trade in history was Babe Ruth for cash

3. It seems to me that very few of the deals that you described as “lopsided” resulted in pennants for the teams receiving the largesse? Is this accurate?

Yes and no.

Very few lopsided trades resulted in a World Championship in the same season that the trade was made. In fact, there are only nine in history. Probably the two most famous of those nine were: 1964 Lou Brock and 1966 Frank Robinson.

However, since 1916, two-thirds of World Championship teams had at least one player on their club acquired in a lopsided trade.

So, the answer is lopsided trades lead to World Championship, but usually not in the first season of the trade. Now the main reason for this is the fact that most lopsided trades involve trading a young, future star. Thus, the Championship comes later when the young player develops into a star.

4. Is a pennant worth a prospect? Tenth on your list is the trade in which the Red Sox gave up the prospect Jeff Bagwell for reliever Larry Andersen. Granted Bagwell went on to a Hall of Fame career, but the Sox would not have won the division without Andersen who in 15 games had an ERA of 1.23 and a WHIP of 0.955. Additionally, the Sox had Hall of Famer Wade Boggs at the time at third.

The one thing I was surprised to find when I did the math on the trades was that mathematically trading deadline deals do not have a very large impact on a team’s performance. In fact, in order for a trading deal to have an impact on a pennant race, the race must be very close and the player acquired most performance at a very high level. In the case of Anderson for Bagwell, Mathematically, the Red Sox win, with or without Anderson.

Trading deadline deals are like intentional walks. In the past, managers constantly used intentional walks to set-up double plays. Then we found out that the strategy doesn’t work. The guy being walked has a better chance of scoring than the next batter has of hitting into a double play. {Don’t you just love stuff like that? BC} Well, deadline deals are similar in the sense that the player being traded away will win on the average more pennants than the one that the team trading the prospect(s) is trying to win. Moreover, if a team needs a player just to make the post-season then chances are that team isn’t good enough to win it all anyway. We saw that two years ago when the Brewers picked up CC Sabathia and the Dodgers picked up Manny Ramirez. Both, CC and Manny played great and carried their club to the post-season. However, both clubs were one-and-done. Thus, in general trading deadline deals are a bad risk.

5. Is there predictive data that can be ascertained by looking at the lopsided trades in the past?

Yes, there is a section of the book entitled red flags where the reoccurring themes of lopsided trades are listed. There are 13 red flags. Here are four of them: (1) Putting too much stock in a pitcher’s won/loss record; (2) Ignoring a pitcher’s walk/strikeout ratio; (3) trading very young hitters; and (4) a general distrust of minor league statistics.

6. When a trade is made, how long does it take before you know it is lopsided? How quickly do you cringe?

Sometimes we all are able to tell right away. This usually happens when an overrated aging veteran is traded for a very good young player (Ryne Sandberg for Ivan DeJesus). Or a pitcher with a great walk/strikeout ratio is traded for one with a poor one (Curt Schilling for Jason Grimsley). Or a speedy player is traded for a slow comparable or lesser hitter (Joe Morgan for Lee May). However, most of the time a trade falls into the red flag category where the conditions are right for a lopsided trade.

There will be a lot of these trades at or near the deadline. The Blue Jays have made a couple of these as of late. Last year at the deadline they traded Scott Rolen for Edwin Encarnacion. This season they traded Alex Gonzalez for Yunel Escobar. Both Encarnacion and Escobar have issues. However, either or both could develop. For now both remain in the red flag pile.

Then of course, there are always a few surprises.

7. Are there certain players who you can sense are so over-rated that they will produce a lopsided deal when he is included (i.e. Curt Schilling was involved in two of your top ten most lopsided deals, is Cliff Lee good or bad to trade?)?

There are generally two kinds of players who show up more than once on the lopsided trade list:

(i) Players with a top on potential but take a while to develop. Yes, Curt Schilling falls into this category. Sammy Sosa is another one. Phil Nevin fell into this category. Nevin was a former overall #1 pick who a traded a few times before he finally started to produce;

(ii) Multi-skilled players. Players who are underrated because they do many things very well, but none extremely well and, consequently, they tend to fly under the “star” radar. We are talking the Ken Singleton, Jeff Kent-type players.

The stars, the top of the talent pyramid guys win pennants. Teams don’t win pennants by trading these guys away. Pennants are won by keeping of acquiring these guys. Thus, it is never recommend trading a Cy Young winner such as a Cliff Lee. The Indians told their fans that they were rebuilding by trading Sabathia and Lee. Teams don’t build by trading their best building blocks {Read that over and over. BC}.

8. If you were a GM, which GM in the bigs now would you be wary of dealing with? Who would you want to deal with?

I don’t really want to name names on this one. However, I can name teams. It is never a good idea to trade with the teams which have great management teams, it is much “safer” to trade with the “weaker” GMs. The teams which scare me are: Tampa and Minnesota (how do those guys win every year with their payrolls?); Boston (the legendary stat guru Bill James is an advisor); Oakland (yeah, I read Moneyball); and Atlanta (those guys are just plain good).

Now the best teams to trade with are the teams who have a different philosophy than your own. The teams who seem to be on a different wavelength than I am are: the White Sox, D’backs, Indians, Giants and Reds. These would be the teams I would probably seek out to make a trade.

Ted and Joe

9. Sorry to make you work on this one, but early in the 1947 season, Joe  DiMaggio and Ted Williams were nearly traded for one another, but reportedly Tom Yawkey sobered up and backed out. I know there are variables that you can’t measure, but who do you think would have gotten the better of that deal?

Not even close. In 1947 and beyond, Ted Williams over Joe DiMaggio by a landside. Ted posted 44 win shares in 1947 to Joe’s 30. After 1947 Ted continued to dominate posting 204 more win shares in his career to more than double Joe’s 101. Thus, you can see why the Yankees wanted to make the deal and why the Red Sox were lucky that Yawkey backed out.

To purchase Traded: Inside the Most Lopsided Trades in Baseball History, by Doug Decatur, head to the Amazon bookstore.

There will be plenty more baseball all weekend long on including news on trades at the deadline.