Sometimes, a team has to make a move when they're in the midst of a pennant race. They make a trade to bring in an established veteran and ship off a prospect, who does a great job that season for the team before heading to free agency.
The prospect, meanwhile, has a Hall of Fame career. It's a story a good number of teams know, and those that do not at least have a similar story to tell. Some trades end up working out so badly, whether in hindsight or from the start, that they become part of a team's lore.
The following is a prospect that every team wishes they did not trade.
In 1988, the Orioles' farm system was stocked with talent after they acquired Curt Schilling and Brady Anderson from the Red Sox to go along with Pete Harnisch and Steve Finley. After the 1990 season ended, that core group left with it.
On January 10, 1991, the Orioles traded Schilling (a reliever for three seasons at that time), Harnisch, and Finley to the Astros for Glenn Davis, a player who did little for them. Schilling was converted to a starter after his stint in Houston and became a postseason legend and interesting case for the Hall of Fame in his career.
Ironically, Schilling and Finley did combine to win a title, just not for Baltimore; they did so with Arizona in 2001.
In 1990, the Red Sox were in the thick of a pennant race and needed a veteran reliever. They got just that from the Houston Astros, who sent them Larry Andersen at the end of August. Andersen had a 1.23 ERA in 15 relief appearances, so he did his job.
The Astros, meanwhile, brought up the player they got in the trade, Jeff Bagwell, and never looked back, enjoying 15 seasons of hitting prowess that the Sox wold have loved to hold onto.
The easy choice here would be Jay Buhner. He became a fan favorite and a key part of the Mariners' rise in the 1990s, and the trade was immortalized on Seinfeld, with Frank Costanza giving Steinbrenner heat over said deal.
However, that's the second-worst trade. The worst was when they traded Fred McGriff to the Toronto Blue Jays after the 1982 season with others for Tom Dodd and Dale Murray, who did nothing. McGriff was still in the rookie league, so it seemed fine at the time.
Instead, he went on to hit 493 home runs and could have been a player to build around during the Yankees teams of the early 1990s.
Technically, the Rays did not trade Hamilton. Given his prowess and the Rays' short history though, this is a notable exception that I wish to touch on.
Hamilton was the first overall pick in 1999, and while he hit well, he dealt with personal demons frequently. In 2006, the Rays had enough of waiting for him, and let him go in the Rule 5 draft. A season later, the Rangers picked him up, and he finally overcame everything and became a star.
The Reds trading Hamilton to the Rangers could be an honorable mention in their own section, for that matter.
The Blue Jays' history is composed mostly of great trades (Joe Carter, Roberto Alomar, among others), so it was difficult to catch the one that got away. Plus, when they do trade great players, it's those who are already established stars, so they don't fit this list.
One that does stick out, however, is Cecil Fielder, a prospect who was great in the minors yet couldn't get things going in Toronto. After four seasons, Toronto gave up on their prospect and sent him to Japan.
After a stint there, he joined Detroit and became one of the most feared hitters of the early 1990s. As good as the Blue Jays were at that time with their two World Series wins, imagine how good they would have been with him in the lineup.
Norm Cash almost made it on the Indians list, but he wasn't a top Indians prospect; he was a top White Sox prospect that got away. In 71 games in two seasons, Cash didn't do much, and to re-acquire Minnie Minoso, the White Sox sent him to the Indians in late 1959 for Minoso and three others, who did nothing.
The Indians traded him to the Tigers, where he was their first baseman for 15 seasons, consistently putting up great numbers and being a key figure for the Tigers throughout the 1960s. The White Sox finished second in the AL three times in the 60s, and Cash could have put them over the hump.
The Indians in the late 1950s seemed to make the worst moves. After having Roger Maris in the lineup for a season and a half, GM Frank Lane made what he called his best move in Cleveland, and traded Maris to the Athletics for Woodie Held and Vic Power.
The two players had nice careers for the Indians, and Power made a couple All-Star teams, but the back-to-back MVP seasons and 61 home runs would have been far more useful in the lineup. His 141 RBI in 1961 equaled Held and Power's output combined that year, and they were supposed to be the big power bats in the lineup.
When the Detroit Tigers traded Billy Pierce to the White Sox in 1948, that was the prospect they wish they did not trade for a long time. Nearly 40 years later, they made Tigers fans forget that one.
In 1987, the Tigers wanted pitching help in the pennant race, and acquired Doyle Alexander from the Atlanta Braves. Alexander was brilliant in 11 starts for the Tigers, but faded out after that. The Braves, meanwhile, brought up John Smoltz.
Smoltz combined with Greg Maddux and Tom Glavine to form the best starting rotation of the 1990s and one of the all-time great ones, for that matter. Smoltz won a Cy Young, 213 games and had a stint as the team's closer for a time, being successful there as well.
This one is admittedly bending the rules, as Cone did not only return to the Royals for a second stint after the first one I'm noting, but won a Cy Young for them.
Having said that, when the Royals traded him to the Mets in early 1987 after one season, they acquired three players that did nothing, while the Mets had a great starter for six years. Cone could have just as easily been a nine-year veteran of the team had they not pulled the trigger so quickly, even if they were able to fix the mistake.
Surprisingly, I found little on prospects they traded; usually said prospects are traded from Kansas City after five or six years in the majors when they become stars, like Carlos Beltran or Johnny Damon.
Since the Twins released David Ortiz rather than trade him, he gets a pass here. Instead, the Twins dealt away a star third baseman during a decade where they needed a mainstay, as they even had to put Harmon Killebrew there for a while since they had no one else.
That player is Graig Nettles. Nettles played three seasons and about 120 games with the Twins, who used him as a utility player. He was traded to the Cleveland Indians with others for Luis Tiant and Stan Williams in December 1969.
While both played well in 1970 for the Twins, Nettles became the Yankees' third baseman in the 1970s and 1980s, hitting 390 home runs during his career. Nettles could have filled the power vacuum when Killebrew and Tony Oliva retired in the mid-1970s.
While the Vernon Wells trade is fast becoming the worst trade in Angels history, there were no prospects involved. In the case of a 1989 trade, they missed out on having a reliable closer for many years.
In August 1989, the Angels traded Roberto Hernandez and Mark Doran to the Chicago White Sox for Mark Davis. Davis played three games, while Hernandez became the White Sox closer for six years, as well as closer for the Devil Rays and Royals.
The Angels missed out on 326 saves in Hernandez's career, though luckily for them after being without a reliable closer for the first half of the 1990s, they found Troy Percival.
Connie Mack made a huge number of trades during his history with the Philadelphia Athletics, usually to keep the money coming in, which resulted in the stars being traded away. In one notable case however, a prospect got away.
After ten games in two seasons, the Athletics traded away the 21-year-old to the Cleveland Naps as a player to be named later to acquire Bris Lord, who did little. Jackson, meanwhile, was a leader of both the Naps and White Sox throughout the dead-ball era.
While the Derek Lowe/Jason Varitek trade is the one commonly referred to as the worst and could qualify on this list, and it does here, Varitek wins over owe here based on what the Mariners needed this past decade.
At the trade deadline in 1997, Varitek and Lowe were traded by Seattle to the Red Sox for Heathcliff Slocumb. The catcher made his debut for Boston later that year, and has been the starting catcher pretty much since.
He had a very solid career behind the backstop, and he was definitely a better catcher than the many the Mariners had while the Red Sox had Varitek.
You can't blame the San Diego Padres for sending Adrian Gonzalez to Boston this past season, as they had to capitalize and get some prospects for him. You can, however, blame the Rangers for shipping Gonzalez off when they had him.
After acquiring him in 2003, Adrian Gonzalez played 59 games in two years in Texas, and was sent to the Padres in 2006 for three players, none who did much (though Akinori Otsuka was a solid reliever for two years).
Gonzalez contributed immediately to San Diego, being the main offensive force for five seasons, and it would not surprise me if he won an MVP or two, as he's just hitting his peak now. I would have let this slide since they had Mark Teixeira at first already, but then they traded him too.
While both Mark Teixeira trades were likely the worst in history, and one of the prospects traded in that could definitely end up on this list, it's too early to say. Instead, the biggest prospect they lost was one of the more underrated hitters of the 1970s and 1980s, Andre Thornton.
Originally a member of the Phillies, Thornton was picked up by the Braves in 1972, only to be dealt a year later for Joe Pepitone. Pepitone played three games for Atlanta, and Thornton went on to hit 253 home runs through 1987.
A tandem of him, Dale Murphy and others could have proven more formidable than what the Braves had back then. Adam Wainwright deserves an honorable mention here, though I left him off since I'd rather wait and see how he performs after Tommy John surgery.
Why does no one seem to want Adrian Gonzalez? You're telling me two teams shipped him off?
That's right. The Marlins were the team that originally drafted him, and did so first overall in 2000. Three years later, during the Marlins improbable run, he was sent to the Texas Rangers with two others for Ugueth Urbina.
They won the World Series, but I'm sure they would have liked to have Gonzalez the rest of the decade.
Nolan Ryan played five seasons with the Mets to start off his career, so it's a bit of a stretch to call him a prospect given that fact. Since he played until the age of 46, however, I think one could still call him a prospect back then.
Ryan made his debut in September 1966, and by the end of 1971 had yet to really show anything. As a result, the Mets traded him to the California Angels with three others for Jim Fregosi. Fregosi played a season and a half with the Mets, while Ryan played 22 more years, setting the all-time strikeout record.
If there is one trade in Phillies history that really bothers the fans, it's this one. In 1981, the Phillies were coming off a World Series win and debuted their newest star, 21-year-old Ryne Sandberg.
After 13 games, he was traded to the Cubs with Larry Bowa for Ivan De Jesus. Bowa and De Jesus canceled each other out, while Sandberg went on to have a Hall of Fame career. The Phillies, meanwhile, had Juan Samuel and a bunch of others holding the fort at second base.
The Montreal Expos have tended to give away prospects when needed. Cliff Lee was a huge prospect to lose, but at least they got Bartolo Colon for that. The same can't be said for the Randy Johnson trade.
After 11 appearances in two seasons, the Expos traded their prospect with others to the Seattle Mariners for Mark Langston. Langston played well for half a season in Montreal, while Johnson became one of the all-time greatest pitchers in Seattle and everywhere else he went.
The Cubs have been on the good end of many of these prospect deals in this list. That being said, the one that involves them was so bad that it's practically the poster boy for these types of deals.
Brock had not done much in three-and-a-half seasons in Chicago, so the Cubs sent him to the Cardinals with two others for Ernie Broglio and others.
Broglio faded quickly, while Brock not only became a catalyst for the Cardinals' 1964 World Series win, but had 3,000 hits in his career and broke the stolen base record in the process, leading to an easy induction into the Hall of Fame.
This was a stupid trade then, is a stupid trade now, and I still struggle to figure this one out. The Cincinnati Reds had acquired the 20-year-old Mathewson in 1900, only to trade him to the New York Giants for 30-year-old Amos Rusie.
Rusie pitched three games in 1901 and showed that his arm was done, while Mathewson pitched in New York for 17 years, winning 373 games and establishing himself as one of the greatest pitchers of all time.
As tempting as it would be to use Curt Schilling, I used him already, and he had four seasons under his belt after he was done in Houston, so I'll go to plan B on this one.
Kenny Lofton played 24 games for the Houston Astros in 1991, and since they had Steve Finley from the Schilling trade, they sent him to the Cleveland Indians for Eddie Taubensee and Willie Blair. Both were mediocre, while Lofton was one of the best hitters and baserunners of the 1990s.
The Astros, meanwhile, traded Finley anyway, so Lofton could have given the lineup of Bagwell and Biggio an extra dimension.
After drafting Sheffield in 1986, the Brewers quickly brought him up the minor leagues, and he made his debut two years later at the age of 19. Once there, he did little for four seasons, as he was stuck behind Greg Vaughn and Dante Bichette.
As a result, the Brewers traded him to San Diego for three players, so Sheffield had major pull as a prospect despite limited playing time. It paid off for San Diego and subsequent teams, and he finished his career with 509 home runs.
The Brewers, meanwhile, traded Bichette as well and fell into mediocrity. They made a great prospect trade of their own to fill the hole left by both with Jeromy Burnitz, but it wasn't the same.
The Pittsburgh Pirates may make plenty of bad trades now, but back in the 1970s they were a solid team that could win championships. That didn't stop the Pirates from shipping off a top prospect though.
In 1975, 21-year-old Willie Randolph had played 30 games for the Pirates and batted .164. Not seeing him as the second baseman of the future, they traded him to the Yankees with two others for Doc Medich.
Randolph had a great career as a Yankee for 13 seasons, while Medich lasted one year in Pittsburgh.
The St. Louis Cardinals were a bad team throughout the dead-ball era. Perhaps they would have been better had they not given away Brown.
Mordecai "Three Finger" Brown went 9-13 in 1903, his rookie year for the Cardinals. He was then traded to the Cubs for Jack Taylor and another player. Taylor did win 20 and 19 games for the Cardinals the next two years, so it wasn't the worst trade ever.
Brown, however, had six straight 20-win seasons, and finished his career with 239 of them.
Brad Penny's not exactly in the company of many pitchers on this list, but the Diamondbacks are a new franchise and as such gave me little to work with.
After the Diamondbacks picked up Penny in 1996, they traded him to the Marlins in 1999 with many others for Matt Mantei. Mantei was a decent reliever, but Penny's multiple All-Star appearances could have helped the Diamondbacks out in the early 2000s.
Being behind Randy Johnson and Curt Schilling in the rotation may have helped too.
If the Rockies have any good prospects, they are good about signing them long term, so the Rockies give me little to work with as well. One that seemed to get away from them, since he wasn't a home run masher, was Juan Pierre.
After three solid seasons with Colorado, they traded Pierre to the Marlins after the 2002 season with Mike Hampton for a bunch of players. His leadoff hitting ended up being instrumental in helping the Marlins with the World Series the following year, and he has since eclipsed the 2,000 hit mark.
The Los Angeles Dodgers, keepers of legendary lefty Sandy Koufax, missed out on a righty who was nearly as good that they had as a prospect, Pedro Martinez.
In two seasons, Martinez showed he had good stuff, going 10-5 with a 2.61 ERA his rookie year. Despite that, the Dodgers traded the 22-year-old to the Expos for Delino DeShields. While DeShields provided some nice speed and defense, Martinez became dominant in Montreal and everywhere else he played.
The scary thing is that the Dodgers has one of the best rotations in the early-mid 1990s ERA-wise. Had they had Pedro leading it, they could have punched a ticket to a World Series or two.
Ozzie Smith and Roberto Alomar actually made All-Star appearances in their final seasons, so I cannot call them prospects, so they get a pass on this list, even though they're the obvious top choices. As such, pretty much the only "prospect" left who was traded before he could show what he could was John Kruk.
After three-and-a-half seasons with San Diego after climbing the minors, one of them great, he was traded to the Phillies with Randy Ready for Chris James. He went on to have three straight great seasons for Philadelphia, and his numbers could have been better had he not abruptly retired in 1995.
The A.J. Pierzynski trade remains the worst in Giants history, and it was tempting to include Joe Nathan on the list. However, there was a prospect the Giants traded away that may have hurt their franchise much more.
After two-and-a-half seasons on the Giants roster, the team had barely used Foster at all, and traded the 22-year-old to the Cincinnati Reds for two players that amounted to nothing. Foster became a key part of the Big Red Machine, hitting 52 home runs and winning the MVP in 1977.