DBWI: The worst trades and signings in baseball history

As a new season in Major League Baseball has begun, here is an opportunity to voice your opinions and which trades and free agent signings rank as the worst in baseball history.

My pick: The New York Mets trade Nolan Ryan to the Texas Rangers before the 1972 season for Frank Howard.

At the time, the Mets pondered trading Ryan for a third baseman but with the Washington Senators moving to Arlington, TX after the 1971 season, Frank Howard was reluctant to move west. With a surplus of pitching, the Mets craved a proven home run hitter and the Rangers were eager to land a native Texan for the publicity.

In Texas, Ryan became the most popular player in team history. He learned how to strike batters out. Although the Rangers finished in last place in 1972 and 1973, Ryan won 20 in 1972 and 18 in 1973. He served as a mentor for a young pitcher named David Clyde (who would be elected to the Hall of Fame in 1998).

In 1974, Ferguson Jenkins arrived and won 25 while Ryan had a 22-12 record with 395 strikeouts to win his first Cy Young. The Rangers finished 91-71 to win its first AL West division title, defeated the Yankees in the ALCs and the Dodgers in the World Series. The Rangers would win the World Series again in 1978, 1980, 1982 and 1983. Jenkins retired after the 1983 season. By the time Ryan retired in 1994, he pitched 8 no-hitters and had more strikeouts and wins than anyone in history. He had consecutive 20 win seasons from 1977-1985 and passed Cy Young on the all-time wins list in 1989. David Clyde played his entire career with the Rangers until he retired in 1993 with 318 lifetime victories and 3 Cy Young awards.

As for the Mets, Howard went bust. In the last weekend of the 1973 season, Rusty Staub hit 4 home runs to lead the Montreal Expos to the sweep of the Mets and win their first division title. Howard went 1-for-10 in that series and struck out 7 times. He retired after the 1973 season. The Expos won the National League pennant but lost the World Series to the A's.
 
Well, there were three I can think of, although they are not so much bad trades as ones that ended up a bit lop-sided and helping one team far more than the other:

1. The Atlanta Braves traded Dale Murphy to the Milwaukee Brewers for Sixto Lezcano at the start of the 1980 season. It's not that Sixto Lezcano was a bad outfielder. He won a gold Glove in 1982, and he provided solid offense from 1980-1985. But Murphy became a mainstay for the Brewers, playing until 1997, when he retired, having hit 461 home runs over his career, and adding 2,650 hits. He won five Gold Gloves, and two MVPs. Murphy also provided a stabilizing influence for Paul Molitor - heading off what could have been a bad cocaine problem. Molitor's emergence as one of the AL's best second basemen in history can arguably be credited to Murphy's stabilizing influence - he played until 2001, and ended up with 4,264 hits. Had Milwaukee stayed in the AL after 1997, Murphy probably could have DHed for a few years, and gotten 500 homers. Instead, he's arguably seen as the best player not yet in the Hall of Fame.

2. That December 6, 1979 trade, in which Baltimore got reliever Frank DiPino, shortstop Lenn Sakata, and outfielder Dion James for an infield prospect named Cal Ripken. Again, not so much a bad trade for the Orioles since DiPino was a good closer, notching 49 saves from 1982-1984 for the Orioles, and Sakata was okay at shortstop from 1982-1985 for them, and James was a solid reserve outfielder for the O's for five years from 1983-1987. That's pretty good deal for the Orioles, right? Well... when consider that the guy the Brewers got did not miss a game from the start of the 1982 season to the end of 2001, when he retired, it starts to look a little short-sighted. He started at third base, then moved to shortstop when Robin Yount had to move to the outfield in 1985, only to shift back to third in 1989 when Gary Sheffield came up from the minors. Ripken had 472 career home runs, 3,359 hits, and bunches of All-Star selections, and was a first-ballot Hall of Famer. Not only that - he was an effective mentor to Gary Sheffield, who emerged as a great shortstop and outfielder in his own right for the Brewers from 1989 through 2001. Ironically, Sheffield replace Dale Murphy in right field, and would earn two Gold Gloves before he was traded to the Atlanta Braves with shortstop Mark Loretta for shortstop Rafael Furcal and outfielder Andruw Jones. Yeah, that deal didn't work out so well for the Orioles in the long term, and there isn't an Oriole exec who doesn't wish that they had gone for the smaller deal of Sakata for reliever John Flinn, who was up and down between Baltimore and AAA from 1980 to 1984, instead of the bigger offer. Incidentally, Furcal and Jones are mainstays for the Brewers today, along with Ryan Braun, Rickie Weeks, JJ Hardy, and Prince Fielder. Weeks has arguably been one of the best center fielders in the majors. Braun's not the best defensive third baseman, but he still works a lot with Ripken, and his fielding percentage at least stays above .900. He's lead the league in slugging three of the last five years.

3. Infielder Jim Gantner and pitchers Jim Slaton and Bill Castro to the Dodgers for pitchers Fernando Valenzuela and Orel Hershiser in the 1979-1980 offseason. OK, this deal probably won the Dodgers the 1980 World Series, as Castro proved to be a very solid addition to the bullpen that year - his retiring of Pete Rose and Mike Schmidt in the decisive Game 5 of the NLCS was awazing. It also won the Dodgers the 1981 NL Championship, as Gantner took over second base for Davey Lopes and was a solid defender who became known as "Hollywood Jim" for his dazzling pivots on the double play. You'd be happy with that, right? Well, when Valenzuela and Hershiser turned out to be mainstays in the Brewers' rotation for most of the 1980s, especially when the Brewers won six pennants and four World Series from 1982-1988, you have to second-guess the deal that brought you the glory in 1980-1981. When Ted Higuera came up in 1985, the Brewers had a 1-2-3 rotation that was arguably the best in the majors. While Valenzuela, Hershiser, and Higuera did have injury problems in the early 1990s, Valenzuela pitched until 1998, and Hershiser lasted until 2001. Higuera got a 6-year, $21 million deal after 1988, but his injury problems lead to him posting a 25-26 record with a 4.41 ERA from 1989-1994, missing all of the 1992 season - arguably one of the worst signings in Brewers, as Milwaukee was a small-market team, and couldn't afford to mess that sort of thing up.

The Brewers, from 1980-1995, were probably the best team in the majors. Just the AL pennants in 1982, 1983, 1985, 1986, 1987, 1988, 1989, 1990, 1992, 1993, 1995, and 1996 would be hard to refute - then consider the fact that they won nine of those World Series Championships, and had 1994 not been shortened by a strike, they'd have probably had another pennant and another World Championship.

When you look at Selig Stadium at Miller Park today, there is a statue of Ripken, Molitor, Yount and Murphy together, holding that World Series Trophy from 1982. Their numbers have all been retired, and three of them (Yount, Molitor, and Ripken) are in the Hall of Fame. By the way, does anyone remember the fourth member of the infield for those Brewers teams from 1982-1983? Some guy named Cooper, I think, but don't quote me on that...
 
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Not a bad trade from a neutral standpoint but a sore point for Detroit fans: 1963, Detroit front office decides to deal Al Kaline to the Yankees for Mickey Mantle. I don't know how New York fans feel about this but the sight of Kaline in pinstripes has always been sickening to me.
 
Well, every bad trade is a great one from someone else's perspective, and here's one of the greatest "bad deals" ever.

Anyone remember a little thing called the Curse of the Bambino? Yep. The worst thing that ever happened to Boston was Harry Frazee's interest in Broadway. Strapped for cash in 1919, Frazee looked to market his top commodity, pitcher Babe Ruth. Finally, he found his man a few hours south, in the person of one Cornelius McGillicuddy.

Mack was pretty much ahead of his time, realizing that Babe Ruth was exactly what his struggling Athletics needed to stabilize their finances, permanently. With someone like the Babe out there every day, the City of Brotherly Love would provide him a steady revenue stream, in the form of constantly twirling turnstiles. $150,000 in cash later (which, it must be said, was a gutsy move, since Mack wasn't exactly flush, and had tapped out every resource available to him), and the Babe was on his way to Philly.

Ruth was pretty well on his own at first, but Mack's team started to explode in the mid-20s. Fortunately, just as the star power became passé, Ruth was joined by a parade of the brightest lights in baseball history. Grove. Rommel. Cochrane. Dykes. Simmons. Double X. Those names struck fear into the hearts of AL fans, and to this day, when someone's asked to name the greatest lineup in history, they'll say "The Slaughterhouse" to a man.

This one worked out well beyond Philadelphia, though. Let's not forget that Kansas City benefited greatly. If the As hadn't so thoroughly made Philadelphia an AL town, who would have ever thought to move there? I still can't imagine an NL without the Kings challenging for titles year in and year out.
 
Not a bad trade from a neutral standpoint but a sore point for Detroit fans: 1963, Detroit front office decides to deal Al Kaline to the Yankees for Mickey Mantle. I don't know how New York fans feel about this but the sight of Kaline in pinstripes has always been sickening to me.

That one sounds a lot like the 1985 winter meetings trade the Astros made with the Phillies: The Astros sent Nolan Ryan and Denny Walling for Mike Schmidt and Dave Stewart.

Ryan stabilized the Phillies rotation from 1986-1988, until he signed with Milwaukee as a free agent, and Walling proved to be a solid third baseman. Schmidt was solid for two years, but fell off after 1987, and ended his Hall of Fame career in 1989. What kills Phillies fans was the fact that Dave Stewart became a dominant starter from 1987-1990, and he still was pitching over 200 innings when he retired in 1995 at the age of 38.
 
How can anyone not mention the saturday night massacre that sent Andre Dawson to the Havana Marlins a mere 2 years after Dawson being World Series MVP for the cubs??? Everytime I saw their doofus manager Fidel Castro with his cigar and goofy beard and his big fat belly It made me want to throw my shoe at the tv. They picked Havana over Miami for a team??? Seriously?



Can anyone really explain that one to me?
 
Well, every bad trade is a great one from someone else's perspective, and here's one of the greatest "bad deals" ever.

Anyone remember a little thing called the Curse of the Bambino? Yep. The worst thing that ever happened to Boston was Harry Frazee's interest in Broadway. Strapped for cash in 1919, Frazee looked to market his top commodity, pitcher Babe Ruth. Finally, he found his man a few hours south, in the person of one Cornelius McGillicuddy.

Mack was pretty much ahead of his time, realizing that Babe Ruth was exactly what his struggling Athletics needed to stabilize their finances, permanently. With someone like the Babe out there every day, the City of Brotherly Love would provide him a steady revenue stream, in the form of constantly twirling turnstiles. $150,000 in cash later (which, it must be said, was a gutsy move, since Mack wasn't exactly flush, and had tapped out every resource available to him), and the Babe was on his way to Philly.

Ruth was pretty well on his own at first, but Mack's team started to explode in the mid-20s. Fortunately, just as the star power became passé, Ruth was joined by a parade of the brightest lights in baseball history. Grove. Rommel. Cochrane. Dykes. Simmons. Double X. Those names struck fear into the hearts of AL fans, and to this day, when someone's asked to name the greatest lineup in history, they'll say "The Slaughterhouse" to a man.

This one worked out well beyond Philadelphia, though. Let's not forget that Kansas City benefited greatly. If the As hadn't so thoroughly made Philadelphia an AL town, who would have ever thought to move there? I still can't imagine an NL without the Kings challenging for titles year in and year out.

It goes both ways with Philadelphia, remember Dennis Eckersley? After 16 saves in 1987, the A's trade him to Hollywood for prospects. None of the prospects get past AA, the A's spend 10 years in the basement of the AL.

With Eckersley as closer, averaging 20+ saves a year, the Stars win 8 PCL pennants, 2 Wild Card pennants and three World Series.
 
It goes both ways with Philadelphia, remember Dennis Eckersley? After 16 saves in 1987, the A's trade him to Hollywood for prospects. None of the prospects get past AA, the A's spend 10 years in the basement of the AL.

With Eckersley as closer, averaging 20+ saves a year, the Stars win 8 PCL pennants, 2 Wild Card pennants and three World Series.

Reminds me of the Plesac trade prior to 1992. The Brewers thought Doug Henry was the answer as their closer, and Plesac was slumping. So they send him to Houston for Al Osuna.

Osuna gave them two years before he was flipped to the Dodgers for a player to be named later.

Plesac rebounded from the 1991 slump to become an above average reliever for a dozen years.

Now, that player to be named later acquired in 1994 by the Brewers for Osuna? Roger Cedeno, who became a solid center fielder for the Brewers after Yount retired.
 
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