Every MLB Franchise's Worst Mistake That Cost Them World Series Championships

Nobody is perfect: no person, no player, no team. The world of baseball knows that oh so well. Where else can a player fail 7 out of 10 times and still be a great hitter? Baseball has all of these idiosyncrasies that make the game unique but also so exhilarating. When it comes to building a franchise, if an organization was perfect with all of their moves; it would take the fun out of the game. Every franchise has provided some head-scratching moments throughout their histories, some clearly more than others. Drafting the wrong guy, making an impulsive trade, hiring the wrong manager….the list goes on and on as to what can derail a franchise from winning the World Series.

While some mistakes are easy to cover up; others linger and can set a team back for years or even decades *cough trading Babe Ruth*. Could the Red Sox have won dozens of World Series while the Yankees went 86 years in between championships? It’s possible and it’s always fun to speculate as to what would have happened (Bill Simmons has made a career out of it). Thus, we will look back at the single biggest blunders in each team’s history. With that being said, here is every MLB franchise’s worst mistake that cost them World Series championships.

30 Arizona Diamondbacks – The 2009 Draft

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The 2009 MLB Draft was supposed to represent the start of the next era of Diamondbacks baseball, and for good reason. The team had not one, not two, not three, not four, but five 1st round picks. Based simply on the odds you would think that the team would hit a home run on at least one of the picks; but their best selection, A.J. Pollock is more like a double due to his injury history. The other picks could best be classified as a single (Chris Owings) and three outs as the other three players combined to play just 57 games in the majors.

Ironically, the D-Backs would get their home run in the 8th round as they drafted Paul Goldschmidt but the failed in 4 of their 5 first round attempts to surround Goldy with talent. Arizona also missed two chances to draft the best player in baseball as Mike Trout would fall to the 25th overall selection in that year’s draft.

29 Atlanta Braves – Did Not Give The Ball To John Smoltz Enough In Postseason

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Arguably the greatest pitching trio in MLB history only had one great member come October and that was John Smoltz. Greg Maddux and Tom Glavine may each have more Cy Young Awards than Smoltz, but those two seemed to lose their cool when the stakes were at the highest. With the Braves, Maddux had an 11-13 postseason record while Glavine had a 12-15 record. Smoltz, who was the #3 starter in the rotation, posted a 15-4 record and had a 2.67 ERA compared to a 3.33 mark in the regular season. Even though the Braves did win the World Series in 1995, they lost four other World Series during the 1990s so that whole era has to be considered a bit of a disappointment. Whether it was due to the stubbornness of Bobby Cox, or the pride of Maddux and Glavine; this simple flip in the rotation could have led to more rings for the Big Three.

28 Baltimore Orioles – Trading Curt Schilling, Steve Finley And Pete Harnisch For Glenn Davis

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It’s one thing to trade a future All-Star away; it’s another thing to trade three future All-Stars away but that’s what the Orioles did in 1991. The team was in need of power so they traded for former two-time All-Star Glenn Davis…key word: former. Davis’s best days were behind him and he would never sniff another All-Star selection after being acquired by Baltimore. To acquire Davis, the Orioles sent the Houston Astros pitchers Curt Schilling, Pete Harnisch, and outfielder Steve Finley. All three players would go on to become All-Stars and would combine for nine All-Star selections. Harnisch is the only one that would be an All-Star with the Astros but Finley would become the sixth player with 300 home runs and 300 stolen bases. Schilling would make his fair share of headlines off the field but would win three World Series and is knocking on the door to the Baseball Hall of Fame.

27 Boston Red Sox – Trading Away Babe Ruth

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It’s hard to imagine an MLB team having financial issues but that was what led to Ruth leaving the Red Sox in 1919. The team’s owner, Harry Frazee, was also a theatrical promoter in New York. Despite arguably being the Red Sox best pitcher and undoubtedly being baseball’s best hitter; Ruth became nothing more than a means for Frazee to pocket more money. Ruth wanted a raise after leading the AL in home runs the previous 2 seasons while Frazee needed money to finance his assortment of musicals and plays. Thus, the Red Sox owner sold Ruth to the Yankees for $100,000 after the 1919 season. Frazee didn’t have enough foresight to realize that having Ruth on his team would bring him in more money than the $100,000 he impulsively went after. This trade would start the Curse of the Bambino because after winning 5 of the first 16 World Series played; the Sox would go 86 years before their next World Series in 2004.

26 Chicago Cubs – Drafting Shawon Dunston First Overall In 1982

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With the Curse of the Billy Goat now broken with the Cubs winning the World Series in 2016; it’s clear that it was never a curse to begin with and more of a myth. Something that is factual is the Cubs drafting future journeyman shortstop Shawon Dunston with the number one overall pick in a loaded 1982 draft. In addition to choosing Dunston over other draftees such as Barry Bonds or Randy Johnson; the Cubs also chose Dunston over shortstop Barry Larkin who would go to the Hall of Fame playing for one of the Cubs rivals, the Reds. For much of the 20th century, the Cubs really didn’t stand a chance to compete for a World Series, but they were close a couple of years in the 1980s. They lost in the NLCS in both 1984 and 1989 but things may have been a bit different with Larkin manning the shortstop position.

As for Steve Bartman ‘costing’ the Cubs a World Series; relax, Chicago fans. The Marlins had the better record during the season and the Cubs still had a chance to win the series in Game Seven. Let it go!

25 Chicago White Sox – Trading A 23-year-old Sammy Sosa

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During the 1990s Frank Thomas of the White Sox and Sammy Sosa of the Cubs were two one-man teams who put up great numbers and won MVPs, but had little postseason success. Could things have been different if the two played together? They did for about one-and-a-half years in 1990-91 but the Sox then traded Sosa before the 1992 season. What the Sox netted in return was a 32-year-old George Bell who would retire just two years later. After being a 5-tool player early in his career with the Cubs; Sosa would then become a record-setting home run hitter as the 90s came to a close. Just imagine a White Sox lineup with Big Frank hitting third and Slammin’ Sammy at cleanup. Maybe even Thomas, who strongly opposed steroids in baseball, could have convinced Sosa to stay off the juice. Or maybe Sosa could have turned the already 6’5” 270 lbs. Thomas into a juicer! Either way, it would have been fun to watch the two players co-exist.

24 Cincinnati Reds – Trading For Ken Griffey Jr.

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Griffey Jr. was the most popular player of his era and is Baseball Royalty; but even the most diehard of his fans would admit he was fat and out of shape when he joined the Reds. Who would have thought that Ken Griffey Sr. would have a better career in a Reds uniform than Ken Griffey Jr.? Before trading for Junior, the Reds had won 96 games in 1999 which was their most since their last Big Red Machine World Series in 1976. They were a young and scrappy bunch at the time but the trade for Griffey upset the chemistry of the team. Instead of a group of 25 players; it seemed like the Reds were Ken Griffey Jr. and the other 24 guys. Instead of taking the next step to becoming a championship contender; the Reds took steps back and their win totals went from 96 (1999) to 85 (2000) to 66 (2001). Griffey’s injuries played a part as he missed one-third of the Reds’ games during his tenure and he would never appear in the postseason in a Reds uniform.

23 Cleveland Indians – Using Jose Mesa In Game 7 Of 1997 World Series

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After consecutive All-Star births in 1995 and 1996; the 1997 season wasn’t a good one for Indians’ closer Jose Mesa. He had a rape trial that was ongoing during the season (he was acquitted) and had 5 blown saves compared to just 16 saves. Things, at least on the field, got even worse during the postseason. Despite Mesa blowing two saves in the ALCS, the Indians were able to advance to the World Series where they faced the Marlins. With the Indians up 2-1 in the ninth inning, Mesa came in for the save and seeing how the Indians are still looking for their first World Series since 1948; Mesa clearly did not get the save. He allowed 4 hits and the game-tying run and the Marlins would eventually win in extra innings. Afterwards, Omar Vizquel had this quote about his teammate in that situation: “The eyes of the world were focused on every move we made. Unfortunately, Jose's own eyes were vacant. Completely empty. Nobody home. You could almost see right through him. Not long after I looked into his vacant eyes, he blew the save and the Marlins tied the game.”

22 Colorado Rockies – Drafting Greg Reynolds 2nd Overall In 2006

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After drafting Troy Tulowitzki in the first round in 2005, the Rockies were in the market for a pitcher in the 2006 draft. There were plenty of options including three different pitchers who would become multi-time Cy Young Award winners. But instead of drafting Clayton Kershaw (7th overall), Tim Lincecum (10th overall), or Max Scherzer (11th overall); the Rockies went with Greg Reynolds. Reynolds would win fewer games in his career (6) than the three aforementioned pitchers had number of Cy Young Awards won (7). Not only would taking one of those three pitchers have helped the Rockies immensely; but it would have also weakened their divisional opponents as all three would be drafted by fellow NL West teams. This draft mistake, along with many other miscues, is a big reason why the Rockies have made the postseason just three times in their franchise history.

21 Detroit Tigers – Traded Away John Smoltz

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Smoltz was a local product as he was born just 20 miles from the old Tiger Stadium in Detroit. With the proximity of Smoltz to the Tigers; the team got a good look at him in high school and they saw enough to draft him in the 22nd round in 1985. But just two years later, and without ever pitching in the majors, the Tigers gave up on the Detroit-product and shipped him to Atlanta. They apparently thought the 20-year-old Smoltz wasn’t worth they got in return which was a 36-year-old Doyle Alexander. Alexander would actually be an All-Star in 1988 but then led the AL in losses in 1989 and retired afterwards.

Meanwhile, Smoltz would become a Cy Young winner and Hall of Famer with the Braves. He went from starter to closer to starter and played in 5 World Series, winning one. What could have been if the Tigers were more patience with Smoltz and let him develop and pitch for his hometown team?

20 Houston Astros – Let Randy Johnson Walk

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During the late 1990s the Killer B’s Astros experienced their first taste of the postseason as they made the playoffs in 1997-1999. In 1998 they went all in and traded Carlos Guillen and Freddy Garcia, two future All-Stars, for Randy Johnson. The Big Unit would nearly win the NL Cy Young with a 10-1 record in Houston despite pitching just two months in the National League. The Astros would lose in the NLDS though it was of no fault to Johnson who had a 1.93 ERA in 14 postseason innings. It was thought that the next year would be the Astros’ year but instead of re-signing Johnson, they let him walk to Arizona who had just gone 65-97 in their debut season. So not only did the Astros lose their prized trade deadline addition, but they also only got two months of compensation for Guillen and Garcia. The team used its cap space to bring back Ken Caminiti who was years past his prime. Johnson would go on to win a ring in Arizona while the Astros are still searching for their first World Series win.

19 Kansas City Royals – Never Upgraded Bullpen

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From 1976-78 the Royals went to three straight ALCS only to fail each time to the Yankees. Losing to the Yankees is nothing to be ashamed about but how the Royals came up short was preventable. In 1976 the Royals bullpen gave up a series-losing home run in the 9th inning of Game 5. One year later, KC’s pen again faltered in Game 5 as they allowed 3 runs in the 9th inning. KC was sparred another Game 5 collapse in the 1978 ALCS as they lost to the Yankees in 4 games.

The Royals would overcome all of this in 1980 as they beat the Yankees 3-0 in the ALCS and advanced to the World Series. But, wouldn’t you know: different opponent, same outcome. The Royals faced the Phillies and they had a 3-2 lead until the “Curse of Game 5 9th innings” struck again as the KC bullpen allowed 2 runs which enabled the Phillies to take the lead and win the game. The Royals would then lose Game 6 and lose yet another shot at a World Series.

18 L.A. Angels – Signing Albert Pujols To A 10 Year Contract

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When will these teams learn about signing players over 30 years old to 10 year deals? After being the best player in baseball during the first half of his career; a then-32-year-old Pujols signed a $254 million deal with the Angels, complete with a no-trade clause that will keep him in Anaheim until 2021. Pujols began to decline during his last couple of years in St. Louis and he has fallen off a cliff since heading west. The Angels are now stuck with a DH-only player who hits .240 and will make $140 million over the next five seasons. The contract is tying up the Angels payroll and, as a result, they will be wasting away the prime of the best player in the game, Mike Trout. If/when Trout heads east and wins a World Series with a different team, Angels fans will be wondering why Trout couldn’t win a World Series in their uniform. They have to look no further to Pujols’ disastrous contract which has hamstrung the franchise.

17 L.A. Dodgers – 2004 Draft Misses

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The Clayton Kershaw-era Dodgers have made the postseason six times but have yet to advance past the NLCS. You think things would have gone differently if the Dodgers wouldn’t have missed on all 3 of their first round picks in 2004? Scott Elbert, Blake DeWitt, and Justin Orenduff would combine to post 3.4 WAR in their careers as the Dodgers squandered an opportunity to surround Kershaw (drafted in 2006) with other young talent. To make things even exponentially worse, in the 19th round the Dodgers drafted a high schooler out of Tennessee by the name of David Price. However, Price and the team couldn’t agree to a deal so Price instead went to Vanderbilt and re-entered the draft three years later. Neither Price nor Kershaw may have helped the Dodgers in the postseason, but at least they could have helped the team reach the postseason.

16 Miami Marlins – The Fire Sale After 1997

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In just their fifth season of play; the then-Florida Marlins won the 1997 World Series in a thrilling seven games over the Cleveland Indians. So what did the team due as a means to repeat? They got rid of every meaningful player from their title-winning team at the mandate of owner Wayne Huizenga. He said that the franchise lost $34 million in 1997 despite winning the World Series and, unlike the players, coaches, and GM; the owner’s job is to make money. Thus, the Marlins had to slash payroll and their 1997 payroll of $53 million was cut to $13 million by mid-1998. The team traded six former All-Stars during the 1998 offseason including Kevin Brown, Moises Alou, and Al Leiter. Then during the season they traded another 4 All-Stars including Gary Sheffield was traded for Mike Piazza and after 5 games with the Marlins, Piazza was then traded away. The result: the Marlins became the first team ever to win a World Series one season and then finish in last place in their division the next season.

15 Milwaukee Brewers – Overworked Rollie Fingers

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The 1982 Brewers had everything needed to be a champion. They led the AL in runs, home runs, and OPS and also led in both wins and saves. However, the man who accumulated most of those saves, Rollie Fingers, was worked into the ground during his time in Milwaukee and was injured before the team made it to the 1982 postseason. The team was still strong enough to advance to the World Series but that is when their bullpen fell apart without Fingers, who won both the Cy Young Award and the MVP in 1981. The Brewers had leads in 5 of the 7 World Series games, but would end up losing the series to the Cardinals 4 games to 3. Fingers was so badly injured that he missed the entire 1983 season as well while the Brewers would miss the postseason entirely in that season. They haven’t sniffed the World Series since then and have made just two playoff appearances in the 34 years since coming up one game short.

14 Minnesota Twins – Traded Tom Brunansky After Winning World Series

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The Twins claimed their first World Series in 1987 and brought back their entire starting lineup the following season. However, Twins management then shocked their fans by trading Tom Brunansky just a month into the 1988 season. Not only did the disrupt team chemistry, but the Twins lost their second-leading home run hitter and Twins star Kirby Puckett lost some protection in the lineup. Brunansky was just 27 and the player the Twins acquired was 32-year-old Tom Herr who complained about living in Minnesota and hit just one home run for the Twins. The Twins would not get a chance to defend their title as they would miss the playoffs in each of the next three seasons. It wasn’t until 1991 when the team signed Chili Davis Brunansky’s void would be filled and, wouldn’t you know; the Twins won the World Series again that year.

13 New York Mets – Drafted Steven Chilcott Over Reggie Jackson

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Who knew that Mr. October could have been playing in New York from the start of his career? Instead of selecting Jackson first overall in 1966, the Mets went with Steven Chilcott, a high school catcher out of California. Chilcott’s bad luck with injuries gives him the misfortune of being just one of two number-one picks to never appear in an MLB game. He suffered shoulder injuries while in the minors, which is the worst possible body part to injure as a catcher, and would retire at the age of 24. Jackson would go on to retire 5th all-time in home runs and win five World Series including two for New York’s other baseball team. The Mets would win their first World Series in 1969 but they may have passed up on a potential dynasty by passing on Reggie Jackson.

12 New York Yankees – Overworking Mariano Rivera In 2001

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It’s almost sacrilegious to call anything that Mariano Rivera did in pinstripes a mistake, so this blunder falls more on Joe Torre. During the 2001 regular season, Rivera pitched 80.2 innings which was his most ever as a closer. With an unreliable bullpen, Rivera had many outings that stretched longer than his normal 1-inning save. During Game 7 of the 2001 World Series, the Yankees were leading 2-1 in the eighth inning and Torre, again, turned to his closer for an extended save. Rivera got through the 8th inning with no issues but then fell apart in the 9th inning. Everyone remembers the Luis Gonzalez series-winning hit off Rivera; but they forget what led up to that. Clearly fatigued, Rivera gave up a single, had an uncharacteristic throwing error, allowed a double, and hit a batter before Gonzalez even came to the plate.

Torre’s overworking of Rivera showed up at the worst possible time and the Diamondbacks would shock the world by beating the Yankees in the World Series. Rivera’s postseason career would span 96 games and he would record 42 saves, 8 wins, and this single loss.

11 Oakland Athletics – Commitment To Moneyball

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Moneyball (noun) – A baseball philosophy that’s good enough to win games but not good enough to win championships. In some people’s eyes, Moneyball was GM Billy Beane’s attempt to field a cost-efficient team that was just good enough to not cause fans to revolt. How does a team with the trio of Zito, Hudson, and Mulder, plus MVPs in Giambi and Tejada not even win a playoff series? By being cheap at other areas of the team. None of those five players were even with the team after the age of 30 as once they were done with their first contracts; they were done in Oakland.

Beane has a little too much confidence in his minor league system and believes that anyone can be replaced. He sets a certain price tag on each player and if they deem themselves above that price tag, then they’ll likely be shipped out of town. Connie Mack and Charlie Finley must be rolling over in their graves at what’s going on with their beloved Athletics!

10 Philadelphia Phillies – Throwing Down And In To Joe Carter

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In 1993 the Blue Jays had a 3-1 lead over the Phillies in the World Series. But after a shutout performance by Curt Schilling in Game 5, the momentum seemed to be on Philadelphia’s side. Things were looking good in Game 6 when the Phillies scored 5 runs in the 7th inning to take a 6-5 lead. In the 9th inning, they brought in their closer, Mitch Williams, who had 43 saves on the season to finish the game out and force a Game 7. After allowing a walk, recording an out, and then allowing a single; Williams had two Hall of Famers on base (Rickey Henderson, Paul Molitor) with Joe Carter coming to the plate. After getting to a 2-2 count, Williams meant to keep the pitch on the outside of the plate but it was down and in and right in Carter’s sweet spot. He hit it over the left field wall for a World Series-winning walkoff home run. Afterwards, Williams said, “I'm not going to go home and commit suicide…I wish I hadn't thrown it down and in to Carter. I was trying to keep the ball away from him. It was a mistake.” It wasn’t just a mistake; it was the biggest mistake in Phillies history.

9 Pittsburgh Pirates – Letting Barry Bonds Leave For Nothing

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Despite going to three straight NLCS in the early 1990s, most knew that Bonds’ time in Pittsburgh was coming to an end. He was unhappy the team had traded his best friend Bobby Bonilla and he was even more unhappy about his contract despite being a two-time MVP. The Pirates could have traded Bonds for a collection of young MLB talent and prospects just as the Mariners would eventually do with Ken Griffey Jr. Instead, they held on to him until the bitter end and he walked away with Pittsburgh getting nothing in return. Not only was the Pirates’ quest for a 4th straight NLCS over; but they wouldn’t even be competitive as they had a losing record in each of the next 20 seasons.

To rub salt on the wounds of his former team and despite signing the largest contract in MLB history; Bonds elected to be paid less in his first year with the Giants than what he received in his last year in Pittsburgh.

8 San Diego Padres – Trading Ozzie Smith

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In 1980 the Padres let Dave Winfield sign with the Yankees. That move was inevitable as they offered him the largest contract in MLB history and the small-market Padres couldn’t match it. But the next year the team traded Ozzie Smith to the Cardinals in a move that could have, and should have, been avoided. Smith and the Padres owner had a contentious relationship and it deteriorated to the point that Smith considered waiving his no-trade clause to join the Cardinals. Smith did eventually accept the trade and made this comment about the Cardinals owner: “He made me feel wanted, which was a feeling I was quickly losing from the Padres.” The Winfield and Smith moves would mean that Tony Gwynn (who debuted one year later) spent most of his tenure in San Diego as essentially a one-man team. Outside of a 20-year-old Roberto Alomar and a nearly 40-year-old Rickey Henderson; Gwynn played with no other Hall of Fame batters during his career.

7 San Francisco Giants – Removing Russ Ortiz In Game 6 Of 2002 World Series

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The closest Barry Bonds ever got to a World Series was in the 7th inning of Game 6 of the 2002 World Series. The Giants were leading the Angles 3-2 in the series and were leading that game 5-0 at the seventh inning stretch. But manager Dusty Baker would remove Giants pitcher Russ Ortiz in the 7th inning despite him allowing 0 runs and just 4 hits up to that point. The Angels would score 3 runs in the bottom of the 7th and then 3 more runs in the bottom of the 8th to take a 6-5 lead they would not relinquish. The Angels would then win the World Series by winning Game 7 which also happened to be Baker’s last game as Giants skipper.

Despite making it to Game 7 of the World Series, the team did not welcome Baker back the following season and it wasn’t until Bruce Bochy took over in 2007 that the Giants got back to their winning ways.

6 Seattle Mariners – Drafted Jeff Clement In 2005

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The 2005 MLB Draft is one that will go down in history as one of the most loaded in history. It produced nearly two dozen future All-Stars and some likely Hall of Famers. You seemingly couldn’t go wrong if you picked at the top as 6 of the first 7 picks would be future All-Stars. However, the poor Seattle Mariners had the misfortune of picking the one player who would not be an All-Star, catcher Jeff Clement. The former All-American at USC would barely be an MLB player as he lasted just 152 games in the majors. The Mariners skipped on such players as Ryan Zimmerman (drafted 3rd), Ryan Braun (drafted 4th), Troy Tulowitzki (drafted 7th) and Andrew McCutchen (drafted 11th). Clement would contribute a WAR of -1.2 through his MLB career which is the 5th worst among any catcher ever drafted in the first round. Instead of getting a transcendent talent, the Mariners drafted a bust and the team has still yet to recover.

5 St. Louis Cardinals – Wouldn’t Give Steve Carlton A Raise

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Why would a team trade a 27-year-old three-time All-Star: $12,500. Yep, that was the difference in salary that led to Carlton becoming a Hall of Famer in Philadelphia instead of St. Louis. Carlton wanted a raise from $50,000 to $70,000 while the Cards would not go over $57,500. Carlton would go on to win 4 Cy Young Awards and 241 games with the Phillies while the pitcher St. Louis traded for, Rick Wise, won 32 games with the Cards. Carlton could have been the Cardinals next Bob Gibson but instead the team would go a decade without even making the postseason. The Cardinals, winners of 11 World Series, haven’t made too many mistakes in their history but this lopsided trade is one that set the franchise back about a decade.

4 Tampa Bay Rays – Deployment Of David Price In 2008 Season


After 10 straight losing seasons, the Tampa Bay Devil Rays dropped the devil and re-branded themselves the Tampa Bay Rays. During the Rays rookie season of 2008, they called up another rookie, David Price in September. Price was the first overall pick in 2007 so much was expected of him and the Rays used him in just five games during the regular season and only once as a starter.

The Rays didn’t want to put too much on Price’s plate come postseason so they again used him out of the bullpen even though he was one of their best pitchers. That move ended up possibly costing the Rays their first World Series as every Tampa starter outside of James Shields struggled in the World Series vs. the Phillies. Joe Maddon may be the best skipper in the game, but looking back at this series, he would probably admit he should have just went with the hot arm of Price.

3 Texas Rangers – Started Matt Harrison In Game 7 Of 2011 World Series

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Harrison had won 14 games for the Rangers during the regular season but he didn’t have the best postseason. In three postseason appearances before even reaching the World Series; Harrison had posted a 4.22 ERA which was nearly a run over his regular season ERA. Harrison then got the start in Game 3 of the World Series and couldn’t even get out of the 4th inning. He gave up 3 earned runs (5 runs total) in just 3.2 innings. Despite having Game 4 winner, Derek Holland, on his standard rest of four days; Rangers’ manager Ron Washington decided to give the ball to Harrison and he would come to regret that decision. Harrison gave up 2 runs in the first inning, a third run in the 3rd inning, and pitched just 4 innings total. He was actually spotted a 2-0 lead but once the Cardinals took the lead in the 3rd inning, they would never give it back.

2 Toronto Blue Jays – Neglected The DH Position In 1991

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The Blue Jays only two championships are when they won back-to-back World Series in 1992 and 1993. 1994 was the strike so they couldn’t have three-peated that way, but they had a very good shot at winning a World Series in 1991. They advanced to the ALCS but it could have been more had the team invested in its designated hitter position. A combination of Rance Mulliniks, Mookie Wilson, and Pat Tabler manned the position and they combined for just 5 HRs and each had an OPS under .700. The Blue Jays desperately needed another bat in the heart of the order, and they would get it, but it would be a year later. In 1992 the team had future Hall of Famer, Dave Winfield, as the DH and he led the team in OPS on the way to the franchise’s first World Series. The next year they replaced one Hall of Famer with another as Paul Molitor slid into the DH position. He would lead the league in hits as the Blue Jays captured their second World Series championship.

1 Washington Nationals – Fire Sale After 1994 Season

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In a couple of years, letting Bryce Harper sign with the Yankees may be the Nationals biggest mistake, but for now, the franchise’s fire sale after the strike of 1994 takes the top spot. The then-Montreal Expos had the best record in the majors in 1994 and only a strike kept them from the World Series. While you would assume the team would reload for the following season; the owner had other ideas. He had a fire sale of most of the team's top players as Larry Walker, Marquis Grissom, Ken Hill, and John Wetteland were all either traded or not re-signed. As a result, the team won 8 fewer games the next year despite playing in 30 more games! Not even Pedro Martinez winning a Cy Young in Montreal nor an up-and-coming Vladimir Guerrero could save what have been done with the penny-pinching ways of ownership. The Expos would exist as the Expos up until the 2004 season and then they were relocated to Washington to become the Nationals.

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