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40 Catastrophic Moves MLB Teams Still Regret to This Day

Dan TylickiAnalyst IDecember 13, 2016

40 Catastrophic Moves MLB Teams Still Regret to This Day

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    Since free agency began, there have been some awful signings. During the trade deadline, awful decisions are made.

    This slideshow is not about those merely bad trades.

    This slideshow is about the moves that, for whatever reason, seemed to mess with the psyche of a team. These are moves that look terrible on a stat sheet, of course, but they're moves that stick in the minds of fans as reminders not to make that mistake again.

    These are 40 of those moves. From the bad signing of Barry Zito to a ridiculous 1900 trade that shaped a franchise, each one has left a mark on baseball fans.

40. Mets Trading Nolan Ryan

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    For whatever reason, teams signed Nolan Ryan and then, after a few years, tried to trade him or let him go, figuring the end of his career had to be in sight. And every year, he proved those teams wrong.

    But the worst story is the team that let him go before he got really good.

    In 1971, Ryan was merely a solid pitcher in the Mets rotation when he was traded to the Angels with many others for Jim Fregosi.

    Once in California, Ryan became a star.

    The Mets could have had a Tom Seaver-Nolan Ryan one-two punch in the NL that could have won a title or two—especially in 1973.

39. Mets Picking Up Mo Vaughn

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    During his years in Boston, Mo Vaughn was a feared hitter—not just due to his high average and ability to hit home runs, but because the guy was just flat-out big. After the 1998 season, the Angels felt they needed that kind of player and signed him to a six-year, $80 million deal.

    He played decent baseball for the first two seasons, but he did not live up to his contract at all. However, the Angels did a smart thing that kept them from regretting the signing and being the team listed on this slide: They pawned him off on the Mets for the final three years, where he played just over a season and looked awful doing it.

    The ramifications for the Mets? GM Steve Phillips was fired, it made it harder to take the Mets seriously, and after being cleansed of the bad deal, the Angels won the World Series in 2002, thanks in part to Kevin Appier, whom the Mets traded for Vaughn.

38. Mets Signing Vince Coleman

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    OK, I promise, no more Mets moves after this for a little while.

    The speed demon of the St. Louis Cardinals signed an expensive deal with the Mets, where he failed to crack 100 games in three seasons of play.

    Why he's on here, however, is due to his terrible attitude playing there. From breaking Dwight Gooden's arm to throwing a firecracker in the stands, it made the Mets look like a team you did not want to play for.

37. Rockies Signing Denny Neagle

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    This signing isn't all that terrible on its own, but when combined with another one much higher on the list, the regret becomes a lot clearer.

    Denny Neagle had a career year in 1997, then three half-decent years after that. Despite that, the Rockies paid big money to sign Neagle: five years and $51 million.

    The payout was a 19-23 record and 5.57 ERA.

    2001 was the first year in which the Rockies were able to make a big free-agent splash and show what they could do. Instead, they ended up with a nearly historically bad rotation. If they hadn't had Jason Jennings, who knows how bad the pitching would have looked.

36. Yankees Picking Brien Taylor First in Draft

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    In the late 1980s and early 1990s, the New York Yankees did not have much going for them. In particular, their rotation was bad. As such, they selected high school phenom Brien Taylor first overall in the 1991 MLB draft.

    This isn't too high on the list since it wasn't really the Yankees' fault that Taylor got into a fight and had his career sidetracked, becoming one of three baseball players drafted first to not make the majors.

    Had it worked out, though, Andy Pettitte, David Cone and Taylor could have made winning World Series titles look even easier.

35. Mariners Trading Omar Vizquel

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    The Seattle Mariners teams of the late 1990s had great power hitters, great pitching and alright defense. They did originally have great defense, mainly at the shortstop position, but they sent that packing.

    After the 1993 season ended, the Mariners sent Omar Vizquel to the Indians for Felix Fermin, Reggie Jefferson and cash. Both players were solid in 1994, but then they were done. Vizquel, meanwhile, helped the Indians to two World Series.

    The Mariners had many pieces to be a contender; perhaps they would have been the ones in a couple World Series with Vizquel.

    I almost did not include this one, though, since the Mariners lucked out: With Vizquel gone, they had to bring up a 20-year-old to play shortstop. His name was Alex Rodriguez.

34. Padres Picking Matt Bush First in Draft

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    I have some sympathy for the Yankees picking Brien Taylor for reasons I've mentioned already. When the Padres selected Matt Bush in 2004, however, it did not make sense.

    Drafted as a shortstop, Bush only played one full minor league season with San Diego, hitting .221. In fact, he was almost a complete non-factor until 2011, spending the year with Tampa Bay as a reliever for their AA club.

    As a small-market team, San Diego can't afford to draft players with such high picks who don't even make the major leagues.

33. Braves Signing Bruce Sutter

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    The longtime closer for the Cubs and Cardinals was a nice target after being granted free agency following the 1984 season. To bolster their bullpen, the Braves signed Bruce Sutter to a six-year, $10 million deal.

    While it doesn't sound like much now, it was a big deal then. It was a big deal in particular because Sutter only pitched three of those seasons and was effectively done when he signed with the team.

    As for the regrets, he is still being paid through an insurance policy, as Atlanta pulled a Bobby Bonilla with his contract. Besides, the Braves spent the late 1980s rebuilding, so a veteran closer would not have helped much anyway.

32. Giants Trading for A.J. Pierzynski

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    This is a move that was considered catastrophic five years ago—three years ago even—but has now simply become known as a bad trade that perhaps wasn't quite as lopsided as it was made out to be.

    A.J. Pierzynski was a solid hitting catcher for the Twins. After the 2003 season ended, the Giants felt they needed one of those, so they traded Boof Bonser, Francisco Liriano and Joe Nathan.

    Nathan ended up being the Twins closer for many years, and when healthy, Liriano has been great. Even Bonser was better than Pierzynski the one year the Giants had him.

31. White Sox Trading Sammy Sosa

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    The Rangers originally traded Sammy Sosa to the White Sox after he played a total of 25 games for them. Then, after three seasons with the White Sox, they didn't see anything that made them think he would be a powerful home run hitter, so they traded him to the Cubs for George Bell.

    Bell's career was pretty much over, and after two seasons, he retired. Sosa, meanwhile, showed the exact power the White Sox were trying to trade for. Imagine a duo of Frank Thomas and Sammy Sosa in a lineup during the 1990s; it almost happened.

    Ignoring the whole steroid issue, the extra power could have helped them compete in the AL Central.

30. Athletics Trading Shoeless Joe Jackson

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    Before he was a member of the White Sox during the infamous 1919 season, Joe Jackson was the team leader of the Cleveland Naps in the early 1910s. How did he join the Naps?

    That happened through the Philadelphia A's, who added him in as a player to be named later when they traded Morrie Rath for Bris Lord. Lord had one nice year, but neither player did that much.

    As for Shoeless Joe, imagine how great the A's teams would have been in the 1910s. After all, they already had the $100,000 infield.

29. Expos Trading Pedro Martinez

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    It's tough to trade your top guy when you feel he will leave in free agency, but you can at least get something for him when you do.

    After the Dodgers traded Pedro Martinez for Delino DeShields—a big regret move in itself—Martinez won the Cy Young Award in 1997. The Dodgers then traded their star to the Boston Red Sox in a move that should have brought in the next three or four great prospects. Instead, all they got was Carl Pavano and Tony Armas.

    How were the Expos after that deal? Well, due to this and the next slide, they're no longer the Expos anymore.

28. Multiple Randy Johnson Trades

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    For whatever reason, trading Randy Johnson always makes at least one team look silly. To start, the aforementioned Expos traded him in a package to the Mariners for Mark Langston. And, as a result, the Mariners had their ace for the 90s. (so, yes, there could have been a Randy Johnson-Pedro Martinez combo)

    For as many bad trades as the Mariners have had, though, they won on both sides here, as they traded him to the Astros in 1998 for Freddy Garcia and Carlos Guillen. It wasn't as regrettable for Houston, as he was solid in half a year.

    For the Expos, though, these kinds of trades explain it all.

27. Cubs Signing Alfonso Soriano

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    The Chicago Cubs have deep enough pockets that they can make some moves when needed. That being said, that doesn't mean they have to give outlandish contracts.

    After Alfonso Soriano had a career year with Washington in 2006, contract offers suddenly came flooding in. He signed with the Cubs for eight years and $136 million. And he actually had two very nice years to start, but subsequent seasons have been disappointments.

    The regret is big here, since current GM Theo Epstein has to work around this contract in order to build the team back up again.

26. Mets Signing Oliver Perez

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    Okay, here come a couple more Mets ones.

    Oliver Perez had a good year for the Mets in 2007 and an okay year in 2008. As a result, the Mets gave him a three-year, $36 million contract. He was ultimately released, with the Mets choosing to eat the rest of the money.

    The Mets seem to end up with this a lot. It's bad management, and that reputation hurts in the eyes of potential free agents.

25. Yankees Trading Jay Buhner

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    Fans of Seinfeld already know why this was a bad trade. After playing 32 games for the Yankees, Jay Buhner was traded to the Mariners for Ken Phelps—a player who not only fizzled out, but was meant to do exactly what Buhner did for Seattle.

    The Yankees were in a rut most of the 1990s as a result of moves like these; heck, one year, their best power guy was Jesse Barfield. The Yankees were fine after a few more years, but even a couple down years is painful to Yankees fans.

24. Dodgers Signing Jason Schmidt

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    This signing shows the problems the Dodgers have had, which have come to a head lately.

    After a few very good seasons in San Francisco, Jason Schmidt signed with the Dodgers after the 2006 season for three years and $47 million.  He then completely fell apart there due to injuries and was barely worth a minimum deal, let alone the one he got.

    The Dodgers continually sign fairly big deals for pitchers, and that's not the only time that's happened (Darren Dreifort)—so it's something the Dodgers have to be weary about.

23. Rangers Signing Chan Ho Park

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    While the Dodgers may have made the earlier bad signing, they did let Chan Ho Park go at the right time. After eight seasons with the Dodgers, Park was a hot commodity in the 2001 offseason.

    The Rangers signed him to a five-year, $65 million deal, and he ended up being completely ineffective. The Rangers had a great lineup at the time that included A-Rod, so they could have contended with some pitching help.

22. Mariners Trading Derek Lowe and Jason Varitek

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    This one is less a huge regret and more a trade that ended a regret, as it was instrumental in helping the Red Sox win in 2004.

    At the 1997 trade deadline, the Mariners traded Lowe and Varitek, both rookies at the time, for Heathcliff Slocumb. Not only was Slocumb ineffective as a reliever, but the Mariners lost two players who are still active today and who could have been instrumental in helping them win a title—especially in 2001.

21. Twins Releasing David Ortiz

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    Most of what is on this list involves bad trades or bad free-agent signings. Rarely do you find a release as bad as this.

    After the Mariners traded David Ortiz (as the player to be named later in an earlier deal) to the Twins, he spent six seasons with them. In his last one, 2002, he hit 20 HR, 75 RBI and had a .272 batting average.

    Yes, they released a guy who was already putting up nice numbers.

    The Twins made the playoffs several times the past decade thanks to a nice lineup, but imagine if you added David Ortiz to an already potent lineup. Maybe that would have won a pennant or two.

20. Yankees Signing Carl Pavano

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    After the 2004 season, the Yankees realized they needed some starting pitching help to win a World Series, and Carl Pavano had just had a career year with the Florida Marlins. As a result, he accepted a four-year deal worth about $40 million to pitch in New York.

    Countless injuries made his stay terrible, but what makes this so regrettable is that not only did he bounce back into a capable starter, but in 2010, when the Yankees were looking for free-agent pitchers, he was at one point the best left on the market, causing the nightmares to fly back again.

19. Rangers Overworking David Clyde

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    When you draft a high school pitcher first overall and he pitches his final high school game in early June, what do you do? If you're owner Bob Short, you put him in the starting rotation just a few weeks later in 1973.

    Yes, David Clyde was thrown to the wolves without any time in the minors—and it showed, as he struggled in two major league seasons. After that, he developed arm trouble and never really recovered from it. As a result, the Rangers possibly missed out on a great pitcher.

    They actually had a nice record in 1974, so there was no need for what they pulled.

18. Mets Trading Tom Seaver

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    For this slide and the next, ask yourself this: How do you trade an ace pitcher—in this case the face of the franchise? Even if you luck out and get great prospects, it looks terrible originally.

    The Mets had to answer this in 1977 when they traded Tom Seaver—who had been Cy Young-quality year after year—to the Reds for Doug Flynn, Steve Henderson, Pat Zachry and Dan Norman, with only Zachry pulling much of anything.

    The Reds, meanwhile, got many quality seasons out of Seaver, and the Mets went back to being cellar-dwellers.

17. Cardinals Trading Steve Carlton

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    As bad as the Seaver trade was, at least he didn't win any Cy Youngs after that. And his best years were with the Mets. Plus, free agency was set to begin, so he may have left anyway. I'm not sure what the excuse is here.

    In the early 1970s, the Cardinals had a historic pitching lineup. They had Bob Gibson as their ace and Steve Carlton as their No. 2—a tandem that had already won one World Series. After seven nice seasons with the Cardinals, they traded Carlton to the Philadelphia Phillies for Rick Wise.

    Yes, they traded straight-up a guy who went on to win four Cy Youngs and who was obviously the heir apparent for Bob Gibson for a moderately good innings-eater.

16. Orioles Signing Albert Belle

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    Albert Belle put up great numbers, yet he just seemed unlikeable. As a result, when the Orioles signed him to a five-year, $65 million deal in 1999, it was an easy one to boo. Belle played for two decent seasons, then abruptly retired.

    The Orioles signed Belle to try and get over the hump of being an average team, but it failed to prevent them from suffering through many consecutive losing seasons.

15. Mets Passing on Reggie Jackson

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    The MLB draft is a crapshoot—especially back in 1966, when they were only on the second one. Still, the Mets ended up making a move that was, in hindsight, downright painful.

    The Mets had a choice first overall between catcher Steve Chilcott and outfielder Reggie Jackson. They picked Chilcott, one of three players drafted first overall to never play a game in the major leagues.

    There were a few years in the 1970s where Jackson could have been the spark plug the Mets needed to make it over the top.

14. Indians Signing Wayne Garland

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    Desperate to be relevant again, the Cleveland Indians made a big splash by signing Wayne Garland for 10 years and $2.3 million following the 1976 season.

    After one decent year, he hurt his arm, and the Indians went back to having no starting pitching for a while. Aside from him and Dennis Eckersley, there wasn't much for the Indians to grab onto, and as a resultm it took another couple decades before they bounced back.

13. Giants Signing Barry Zito

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    After seven very good seasons with Oakland, Barry Zito signed a seven-year, $126 million deal with the Giants that has flat out worked horrendously for them.

    I can't rank this any higher for two reasons. First, at least Zito's actually still playing—that's more than others can say on the list. Second, and more importantly, the Giants had a great pitching staff and have had much success in spite of the bad contract. So while there are regrets, it could have been worse.

12. Mets Signing Bobby Bonilla

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    In the early 1990s, the Pittsburgh Pirates had a rising star in Bobby Bonilla that they knew they wouldn't be able to keep. It seemed like a smart pickup, so that's exactly what the Mets did.

    Five years and $29 million later, Bonilla ended up having three-and-a-half decent seasons for the Mets, and he was shipped to the Orioles.

    He ends up so high on this list, however, because the Mets are still paying him.

    Yes, the Mets still have to pay him about a million dollars a year until 2035. If that's not regrettable, I don't know what is.

11. Orioles Trading for Glenn Davis

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    Who was Glenn Davis? In the 1980s, he was the Astros first baseman, and he was a solid power hitter at a time where 34 HR and 100 RBI wasn't quite as common.

    For whatever reason, the Orioles loved this and traded for him. He played three seasons with the Orioles and didn't do much while there. As for the players the Orioles traded, they were Steve Finley, Pete Harnisch and Curt Schilling.

    Yes, they traded three bona fide major league starters for a guy who fizzled out pretty quickly in the American League.

10. Rockies Signing Mike Hampton

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    Let's get the worst of the free-agent signings out of the way now. Yes, the worst one in history, at least for now, is the Rockies' signing of Mike Hampton.

    The Rockies were looking to be respected and signed a former Cy Young winner who had a solid year for the Mets. The contract they gave Hampton was the most expensive at the time: eight years and $121 million.

    Not only was he shipped out after two bad seasons, but it confirmed that Coors Field is where pitchers go to die. It will always be a hitters park, and whether they want to or not, that's something the Rockies will never be able to escape.

9. Indians Trading Rocky Colavito Twice

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    In the 1950s, after the Indians lost the 1954 World Series to the Giants, there was not much else in the future. The lone bright spot was Rocky Colavito, who put up MVP-type numbers for many seasons. At the end of 1959, the Indians traded him for Harvey Kuenn.

    Colavito continued to produce, and with everyone wanting him back in Cleveland, the trigger was pulled before the start of the 1965 season. As outraged as people got on the first trade, the second one is the one with regrets.

    To bring back a Colavito past his prime, the Tribe gave up Tommie Agee and Tommy John—two players who could have definitely helped the Indians. It took nearly 30 years after the second trade for the Indians to be a threat again.

8. Tigers Trading John Smoltz

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    In 1987, the Detroit Tigers were in the thick of a pennant race and the Atlanta Braves were rebuilding, so the Braves gladly sent over Doyle Alexander. He was great in 11 starts, going 9-0 and doing exactly what he was supposed to.

    Unfortunately, he stunk in the playoffs, and to acquire him, the Tigers sent away pitcher John Smoltz, who ended up becoming a key member of the Braves' pitching dynasty in the 1990s.

    It took nearly 20 years for the Tigers to bounce back, whereas the Braves won division title after division title, practically rubbing that trade in the Tigers' face.

7. Red Sox Trading Jeff Bagwell

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    Just like with the Smoltz trade, the Red Sox needed veteran help for a pennant race, and the rebuilding Astros obliged. In 1990, the Astros sent over Larry Andersen to the Red Sox, where he played 15 great games and had a 1.23 ERA.

    He recorded a loss in the playoffs and was done with Boston after that.

    The Red Sox, meanwhile, had sent over Jeff Bagwell to the Astros, who became the face of the franchise for the next 15 years alongside Craig Biggio.

    The Red Sox could have had that extra power and could have made a pennant run while the Yankees were still bouncing back in the early 1990s.

6. Phillies Trading Grover Cleveland Alexander

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    For eight seasons, Grover Cleveland Alexander was one of the top three pitchers in the majors for the Philadelphia Phillies. The one-two punch with Eppa Rixey kept them in contention, and they made it to the World Series in 1915.

    After the 1917 season ended, the Phillies traded him to the Cubs for $55,000 and two players who did little. Alexander, meanwhile, performed well for the Cubs for another nine seasons.

    The painful part was that, immediately after trading him, the Phillies plummeted in the standings, where they remained for a good 30 years. Now there's a major regret.

5. Cubs Trading Lou Brock

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    It's hard to reverse any curse on a team when the team keeps making trades that cost them wins big time. That's exactly what the Cubs did after having Lou Brock in their lineup for four seasons.

    In 1964, the Cubs sent Brock with two others to the St. Louis Cardinals for Ernie Broglio, the star piece of the deal who ended up splaying poorly in Chicago, and two others. Brock immediately paid dividends and guided the Cardinals to a World Series title that year.

    15 seasons later, the Cardinals had a Hall of Famer. The Cubs, meanwhile, ended up consistently last in stolen bases most of those years, with Jose Cardenal being the only one to provide anything on that front.

4. Phillies Trading Ryne Sandberg

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    Ryne Sandberg is basically who you think of when you think of the Cubs in the 1980s and 1990s. They may not have won, but it's not often that a Hall of Famer is essentially handed to you.

    For 13 games in 1981, Sandberg was on the Phillies, who then traded him with Larry Bowa for Ivan De Jesus. De Jesus has three mediocre seasons, as did Bowa, but Sandberg became perhaps a top 10 second baseman all time.

    There were a few seasons in the 1980s where the Phillies seemed one playmaker away from a World Series title. Sandberg could have been that player.

3. Astros Trading Joe Morgan

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    When you have a player on your team for nine seasons, you'd think you would know what they're capable of. Instead, Joe Morgan spent nine years on the Astros playing solidly, but nothing amazing.

    When Morgan was traded to the  Reds before the 1972 season, his career took off. He won the MVP Award twice, led the Reds to two World Series titles and became so great in such a short time that he really made the Astros look foolish.

    As for the Astros, they got Morgan back for a year and won the NL West that year before falling back down to earth. Why his magic didn't work the first time he was in Houston is surely something that bugs them.

2. Reds Trading Christy Mathewson

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    In 1899, the Cincinnati Reds and New York Giants were both near the bottom of the National League and were ready to make a move. The Reds wanted star pitcher Amos Rusie from the Giants, so they picked him up.

    In return, they sent over 19-year old Christy Mathewson. Rusie was done as a pro, and he retired after three games. The Giants, meanwhile, had Mathewson for 373 wins, 17 seasons and many championships.

    The Reds, though, were stuck at the bottom of the division for most of the next 20 years. To add insult to injury, the Reds and Giants made another trade in 1916 that included Mathewson, meaning he played one game for Cincinnati, just so they could see what they missed out on.

1. Red Sox Selling Babe Ruth

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    The Red Sox sold Babe Ruth to the Yankees for $100,000 in a story we all know. The Yankees became the face of baseball, and the Red Sox ended up without a World Series for 86 years.

    Even with two World Series titles finally in their grasp, you know that the Babe Ruth selling story will never be forgotten in Boston.

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