My 10 favorite bad trades ...

This year marks the 30th anniversary of one of my favorite bad trades in baseball history, the Midnight Massacre deal where the New York Mets traded Tom Seaver to Cincinnati for Pat Zachary, Doug Flynn, Steve Henderson and Dan Norman. The reason I love that trade so much is that every single person in America realized it was a horrendous trade right when it was made. And then, as time went on, it got worse.

That kind of magical bad deal doesn’t happen all that often. Best I can tell, most bad deals fall into one of three categories:

1. The bad deal a team feels forced to make because they are about to lose the player anyway (example: Oakland trades Mark McGwire for Blake Stein, T.J. Matthews and a third guy who was even worse than Blake Stein and T.J. Matthews).

2. The bad deal a team makes because they feel like they are one piece away from being a pennant contender (example: Detroit trades a good young arm named John Smoltz for Doyle Alexander, who does indeed go 9-0 down the stretch and carry the Tigers into the postseason. Bonus info: In his career, Doyle Alexander was traded for Smoltz, Frank Robinson and Pepe Frias).

3. The bad deal a team makes because they badly misjudged their own player’s abilities (example: Boston trades a young Jeff Bagwell for an old Larry Andersen; this is also a Category 2 ... the Sox thought Larry Andersen was important for the stretch run).

In addition, there’s the rare fourth deal: the “Oh my God, does anyone there even understand the rules of baseball” deal. These are very rare. Even some of the worst deals in baseball history – Brock for Broglio, Colavito for Kuenn, Pedro for Delino DeShields, Michael Young for Esteban Loaiza (ugh) – were made with some sort of logic behind them. It was flawed logic. But with those deals it’s a bit like reconstructing a failed crime scene. You could say, “Okay, at least I know what they were TRYING to do.”

I’m fascinated by the trades that never made any sense at all, trades that were obvious flops when they were made and then became catastrophes later. Twenty seven years after the Seaver deal, the Mets traded Scott Kazmir (considered by most people at the time to be one of the top pitching prospects in baseball) for Victor Zambrano (considered by most people at the time to be Victor Zambrano). The deal was universally panned but over time it has gotten much worse. And it still figures to get worse. It’s too early to put the Kazmir deal in my Ten Favorite Bad Trades Ever. But it has a chance down the road.

Here, then, are my ten favorite bad trades (Since I mentioned Seaver, I’m leaving him out):

10. The White Sox trade Sammy Sosa to the Cubs for George Bell (1992).

First of all, the White Sox and Cubs should not make trades with each other. Nothing good can come from that. When you look at the history of these two organizations, you know one of them is going to get ripped off very badly, and Chicago really doesn’t need that kind of tension.

This was the second time Sosa was traded, and it’s true that at this point he was a 23-year-old kid who seemed to have absolutely no idea how to swing a bat so that it actually connected with the ball. Still, everyone understood that the kid had already shown some power and speed, he had not been playing baseball that long, he had a chance.

OK, but that’s just a misjudgment. Here’s why I love this deal: It was made just before the start of the 1992 season – literally just days before, on March 30 – which means there was a high-level meeting among White Sox officials who said: “We just have to get George Bell.” Bell was 32 when the deal was made. He was slow, couldn’t field, didn’t want to field, would rather eat paint than walk and had not been worth a damn offensively in two years. He was not exactly known for those intangibles he could bring to a team either. The White Sox had to have him.

They got him. Bell led the Sox with 25 home runs and battled teammate Steve Sax for the honored statistic of “lowest on-base percentage by a player who used to be considered good” (Sax won .290 to .294). And then Bell fell off a cliff. Sosa, well, you know.

9. Philadelphia trades Fergie Jenkins to Chicago for Bob Buhl and Larry Jackson (1966).

In a way, this deal really falls under Category 3 – the “team misjudged its own player” deal. Jenkins was still a relative unknown when the Phillies dealt him – he had not thrown 15 innings in the big leagues. That said, though, this deal qualifies because there’s really no explanation why Philadelphia wanted Larry Jackson and Bob Buhl. They were both ancient, they were both coming off fairly dismal seasons. And it wasn’t like Jenkins developed years later. He won 20 games each of the next six years.

8. Philadelphia trades Ryne Sandberg and Larry Bowa for Ivan DeJesus (1982).

Maybe it was the .194 batting average in 1981. Maybe it was the 13 RBIs in 403 at bats. Maybe it was the 140 errors he had made at shortstop the previous five seasons. Whatever it was, the Phillies just had to have Ivan DeJesus for the 1982 season. They coveted Ivan DeJesus. They swooned over Ivan DeJesus. So, they traded an over-the-hill Larry Bowa for him, which was fine, but the Baseball Gods (capital letters) will get you when you pine for Ivan DeJesus. The throw-in, Ryne Sandberg, had a fairly decent career.

Bonus: Cleveland trades Harry Chiti to the New York Mets for Harry Chiti (1962).

I always felt the Mets got the better of this deal. Or maybe Cleveland did. Harry Chiti was, apparently, a pretty decent defensive catcher (he could really handle the knuckleball according to his various Internet bios) but I’ve often wondered what it was like being known for only one thing in baseball -- getting traded for yourself. I'll bet the jokes at the bar got old.

7. Texas trades Ron Darling and Walt Terrell to the Mets for Lee Mazzilli (1982).

This is a Category 2 trade – a bad deal a team makes when they feel they are just one piece away from contention – but it still gets on this list because: a.) Texas was nowhere near contention, and b.) There is no possible way they could have seen Lee Mazzilli as that final piece. Mazzilli had hit .228 with no power for the Mets the year before and to prove it was no fluke, he promptly went to Texas and hit .241 with no power. When the season ended, the Rangers looked to trade Maz for the one guy they felt confident could hit worse. And they got Bucky Dent.

Meanwhile Darling won 86 games the next six years and picked up a Gold Glove. Terrell won 58 games the next four years, though he did most of that good work with Detroit. The Mets traded Terrell to the Tigers for Howard Johnson in a classic example of doubling up with house money. Johnson had three 30-homer, 30-steal seasons with the Mets. The best part of this Lee Mazzilli trade is the often repeated story about Texas farm director Joe Klein, who was holding a meeting when he heard about it. He supposedly stood up and said, “Gentlemen, this meeting is over. We’re going to the bar.”

6. Kansas City trades David Cone to the New York Mets for Ed Hearn, Rick Anderson and Mauro Gozzo (Round one, 1987); Kansas City trades David Cone to Toronto for Chris Stynes, David Sinnes and Tony Medrano (Round 2, 1995).

You know, David Cone grew up in Kansas City. Yep, born and raised in the City of Fountains and Boulevards. His hometown team traded him away TWICE – in two of the worst trades in memory. I can’t imagine there is any equivalent in sports.

5. St. Louis trades Steve Carlton to Philadelphia for Rick Wise (1972).

I love this deal for a whole other reason. When it was made, Carlton was certainly the better pitcher. He was a three-time All-Star, he had just won 20 games, he was a strikeout lefty, he was only 26. But Wise was no slouch; he was 25, he had come off a good season for a terrible team (17-14, 2.88 ERA). You might see how St. Louis officials went into the 1972 season optimistic that they might have pulled off a good deal for themselves.

And then, BLAMMO, right away Carlton has one of the 10 greatest pitching seasons in baseball history. His first year in Philadelphia, he goes 27-10, 1.97 ERA, strikes out 310, joins Koufax as the only National Leaguers to win the pitching triple crown since World War II, and he does all this for an absurdly dismal Philadelphia team that only wins 59 games. Now, seriously, how do you go back to your owner after that and say, “Um, I still think that trade might work out for us?”

4. Cincinnati trades Christy Mathewson to New York Giants* for Amos Rusie (1900).

I absolutely love this trade. Obviously, it’s a beauty of a deal because Mathewson (who was 19 when they dealt him) became one of the five greatest pitchers in baseball history while Amos Rusie – who is in the Hall of Fame – pitched exactly three awful games with the Reds.

But here’s what makes this an absolutely classic: Amos Rusie had not played professional baseball in TWO YEARS when Cincinnati made this deal. Rusie had been an incredible pitcher in the early 1890s. He was called the Hoosier Thunderbolt (he changed the game; his fastball almost killed Hughie Jennings and helped prompt the baseball gods to move the mound back to 60 feet, 6 inches). But then Rusie held out for a year in a contract dispute, then he got hit in the head with a line drive and lost his hearing, He also had some arm problems. And he stopped pitching. Two years later, the Reds traded Christy Mathewson for him.

So, essentially this deal would be like, I don’t know, Detroit deciding tomorrow to trade Justin Verlander to the Mets for David Cone.

3. Cincinnati trades Frank Robinson to Baltimore for Milt Pappas, Dick Simpson and Jack Baldschun (1965)

This is actually the classic version of the trade I’m talking about – the trade that makes absolutely no sense when it was made and then makes less sense as time goes on. Robinson had been typically great for the Reds in 1965 and then they traded him, which set off a pretty good outcry in Cincinnati. Then, much like Steve Carlton, Robinson promptly went out and won the Triple Crown. After that, this deal became a part of a line in "Bull Durham:” “Who can forget Frank Robinson for Milt Pappas, for gosh sake?”

2. San Francisco trades Joe Nathan, Francisco Liriano and Boof Bonser to Minnesota to A.J. Pierzynski (2003)

It depends on what happens with Liriano’s health, but I think it’s fair to say: This has a chance to be the worst trade in baseball history. It has all the credentials. Minnesota was dying to get Pierzynski and his attitude off the team – and everybody around baseball except the people in San Francisco seemed to know it.

Meanwhile, Nathan was a 28-year-old reliever coming off a dominant season. Liriano was a 20-year-old lefty who could throw 98 m.p.h. Bonser was a big 21-year-old righty who was a first-round pick, had pitched dominant ball in the low minors and was also named “Boof.” This was one of those deals where scouting directors all over baseball stopped meetings and went to the bar.

The trade turned out even worse than expected. The Giants, who apparently had done absolutely no scouting before this trade, found out that Pierzynski was not always a pleasant fellow, so they released him at the end of the year. Nathan has been one of the more dominant closers ever in his three years in Minnesota, Liriano pitched like Koufax before he got hurt, and Bonser is still called Boof.

1. Kansas City trades Jermaine Dye to Oakland (in a three-way deal) in exchange for Neifi Perez (2001).

This isn’t the worst deal ever. It’s just my favorite bad deal. I remember when the Royals made this trade, I called up general manager Allard Baird and said, “It appears you just traded Jermaine Dye for Neifi Perez. Why would you do that?” He explained to me the Royals really couldn’t afford Dye and that they desperately needed a shortstop – talks with Rey Sanchez had broken down – and Perez was a good defensive shortstop who would hit a little bit.

And I said: “It appears you just traded Jermaine Dye for Neifi Perez. Why would you do that?”

I’ve never seen an everyday player as bad as Neifi Perez in 2002. It wasn’t just his .260 on-base percentage and .303 slugging percentage though that’s a pretty good start (his OPS+ that year was 40. Forty. FORTY!). It wasn’t just his unbelievable lack of speed and terrible base running instincts (he was successful on eight of 17 stolen base attempts). It wasn’t just his surprisingly dreadful defense or his terrible attitude (he once refused to go into a game, then later said he was “joking”). No, it was the idea that he was in Kansas City at all. The Royals had traded Jermaine Dye to get him. All because talks broke down with Rey Sanchez.

Sometime, the pain is too much to bear.

Coming up: The first installment of "Baseball Preview With The Stars."