25 Biggest Cinderellas in Baseball History
Who says there aren't any Cinderellas in baseball?
Well, besides Buck Showalter. Forget him and his years of accumulated baseball wisdom.
It's March, I'm in the fairy tale spirit and I'm not letting college basketball steal all the pixie dust.
No sir. We're slipping on the glass slipper, gut-punching a few stepsisters and running through the 25 greatest underdog teams/players in baseball history.
And though I'm bound to miss a few—or a few dozen—I don't mind. Because I'm sure you'll let me hear it in the comments.
25. 1971 Pittsburgh Pirates
To qualify their Cinderella-hood, I should start by saying that the 1971 Pittsburgh Pirates were plenty good. They won 97 regular season games and buzzed through the San Francisco Giants in a four-game NLCS.
But the Baltimore Oriole team they faced in that year’s World Series was another beast, a 101-win titan that featured four 20-game winners.
When the O’s took the first two games, most folks penciled the defending champs in for a repeat.
Then the improbable, a three-game run that saw them beat Mike Cuellar, Pat Dobson and Dave McNally in order. After losing Game 6, the Pirates responded with a Game 7 road win that would cement one of the great upsets in Series history.
24. 1995 Seattle Mariners
Prior to 1995, the Seattle Mariners had finished over .500 just twice in their 18-year existence and never qualified for the playoffs.
With every losing campaign, the prospect of baseball in the Pacific Northwest grew dimmer and dimmer. This was, after all, the city that had lost its first franchise, the Seattle Pilots, after just one season.
Midway through that strike-shortened ’95 season, it looked like more of the same. On August 20, the Mariners were 53-53 and 12.5 games behind the first-place California Angels.
Then the improbable, a scorching run over the season’s final month and change combined with an epic Angels collapse. The clubs finished the regular season tied, and Seattle capped the comeback by winning a one-game playoff.
In the franchise’s first playoff series they dropped the opening two games to the Yankees before mounting another furious comeback to force a decisive Game 5. Once there, Seattle put a cherry atop their improbable season by walking-off against New York in the bottom of the 11th inning.
The Mariners would lose in the ALCS to the Cleveland Indians, but too much good came from the ’95 season to end on such a sour note.
Randy Johnson became a superstar, Edgar Martinez hit the highest high of his remarkable career, and the indelible image of Ken Griffey Jr. giggling beneath an onslaught of teammates signaled baseball’s salvation in Seattle.
23. 1954 New York Giants
History remembers the 1954 World Series for Willie Mays’ over-the-shoulder grab in Game 1, still the most iconic fielding play in baseball history.
The rest of the Series reads like a snooze. New York goes on to a 4-0 sweep. Ticker tape parade ensues. Janitors sweep canyon of heroes. Everybody smiles.
It wasn’t that simple, or at least it shouldn’t have been.
The 1954 Cleveland Indians were one of the modern era’s best teams. Led by a rotation that featured Bob Feller as its No. 5, the Tribe won 111 games in a 154-game season.
The thought that such a team could be beat, much less swept, was something of a wild fantasy. Even more impressive, the underdog Giants trailed for just seven out of a possible 36 innings.
22. Jim Morris
If Jim Morris’ life story sounds like a Hollywood film, that’s because it is.
Drafted fourth overall by the Milwaukee Brewers in 1983, arm injuries forced the hard-throwing Texan out of baseball before his 26th birthday.
So Morris, like many failed prospects before him, carried on. He became a high school teacher in West Texas and spent the next decade coaching baseball instead of playing it.
After losing a bet against his students, Morris attended an open tryout for the Tampa Bay Devil Rays. To his and everyone else’s surprise, the 35-year-old discovered he could still throw—and hard.
The Rays signed and promoted him to the big club that same September. Though his career lasted just 15 innings, it proved powerful enough to inspire The Rookie, a Dennis Quaid vehicle about his comeback.
And when you’ve inspired a Dennis Quaid vehicle, ya done good.
21. 2007 Colorado Rockies
Though it did not end in ultimate glory, baseball has seen few runs more magical than the one Colorado put together in 2007.
It began in mid-September. A Rockies team whose lone playoff appearance had come in 1995 sat 6.5 games out of first place with 14 games to play.
They would go on to win 13 of those 14 games, tying the San Diego Padres for the NL Wild Card in the process.
A one-game playoff for the final spot featured see-saw dramatics, ending on Matt Holliday’s controversial dash home in the bottom of the 13th.
Not simply content to have a spot at the dance, Colorado went on to sweep their NLDS and NLCS matchups against the Phillies and Diamondbacks, respectively. By the time they reached the championship, a team that had won just one playoff game in its prior existence was on a 21-1 tear.
The Red Sox put an emphatic end to Colorado’s heroics with a sweep of their own in the World Series, but even that was not emphasis enough to erase Rocktober from baseball lore.
20. Connie Mack
Even in an era when baseball was a niche pastime and its patrons far less wealthy than today’s business titans, Connie Mack’s climb to the sport’s highest echelon was a remarkable one.
Mack spent his first decade in professional baseball as a light-hitting catcher, bouncing between small-town teams on small-town wages.
Five years after retirement he accepted a job as manager and part owner of the Philadelphia Athletics. He would hold both positions for the next half century, pressing into an era where men far more privileged than he dominated the ownership ranks.
Yet there he was, an old journeyman backstop running day-to-day operations well into his eighth decade.
19. 2004 Boston Red Sox
By most objective measures, the 2004 Boston Red Sox were certifiable over-dogs.
They had the league’s second-highest payroll and finished the season with 98 wins. Just one year prior they’d come within a game of the World Series.
Mix in 86 years of suffering and an historic comeback, however, and suddenly the slipper fits.
You know the story, I presume?
Roberts, Ortiz, Idiots, Bloody booties—a veritable pick ‘em of story lines lionizing Boston’s backs-to-the-wall triumph against the hated New York Yankees and eventual world championship.
18. David Eckstein
There was a time when little dudes like David Eckstein were the norm at shortstop—the sort of five-foot-nothing sparkplugs who made crotchety old men mutter bromides about “determination” and “playing the game the right way.”
But David Eckstein didn’t play his career in a black-and-white newsreel; he played in the wham-bam Technicolor of the steroid era alongside 6’4” mega-stops. And in that context Eckstein was outdated and unwanted, an electric can opener in a Sharper Image kind of world.
At least that’s what the Red Sox thought when they drafted him in the 19th round of the 1997 draft and subsequently waived him three years later.
The Angels picked him up and let him hit his way into the everyday line-up.
What ensued was a most unlikely career, highlighted by two world championships, two All-Star appearances and a 2006 World Series MVP.
Old men, commence muttering.
17. 2008 Tampa Bay Rays
It is difficult to verbalize how bad the Tampa Bay (Devil) Rays were over their first decade in baseball.
Yes, I could point out how they never won more than 70 games and had finished out of last place only once, but the numbers don’t do it justice. This was a hopeless bunch trapped in a warehouse of a stadium under a stingy and impulsive owner.
Maybe the names will help.
The team’s rosters included players like Wilson Alvarez, Quinton McCracken, Felix Martinez, Ryan Rupe and Jared Sandberg.
And those guys were starters. Yeesh.
People had a sense things were improving in 2008, but no one foresaw the great leap forward that was to come. Tampa (payroll $43 million) sprinted to a 55-32 start and never looked back, winning the AL East over the Red Sox ($133 million) and Yankees ($209 million).
By defeating Boston in Game 7 of the ALCS, they bested the 75-1 Vegas odds set against them at season’s start.
16. 1997 Florida Marlins
The 1997 Marlins were a shock to baseball’s old-school sensibilities—a teal-uniformed expansion franchise exploiting newfangled methods and newfangled rules on their way to the mountain top.
For starters, they were a team built through free agency. By signing the likes of Bobby Bonilla, Moises Alou, Gary Sheffield, Al Leiter, Devon White, Kevin Brown, Livan Hernandez and Alex Fernandez, Florida proved that a team could flood the free market and forgo the staid player development process.
If that wasn’t bold enough, the Marlins were a participant in that year’s postseason by way of the newly formed wild card. A clear affront to the sanctity of baseball’s 162-game season, Florida’s mere presence was a fly on the brandy glass of baseball purists.
More than just show up, the Marlins did work. They swept the San Francisco Giants in the first round and whisked by the Braves in a six-game NLCS to set up a World Series tilt with the long-suffering Cleveland Indians.
And of course, it went down to the wire.
Down to their final three outs, the Marlins rallied against closer Jose Mesa in Game 7 and sent the contest to extra innings. In the bottom of the 11th inning, a base hit by a 21-year-old Edgar Renteria delivered the franchise’s first world championship and sent tremors through the baseball establishment.
15. Albert Pujols
It isn’t so uncommon to find a productive player in the 13th round of the amateur draft.
Steve Finley went in the 13th—so did Rod Beck, Rey Sanchez and Chad Bradford. Heck, even Jim Thome fell that far, and he’s Cooperstown bound.
But Albert Pujols isn’t just a productive player or even a run-of-the-mill Hall of Famer; he is arguably the greatest right-handed hitter in baseball history.
The fact that every team passed on him 12 times defies logic.
Many thought Pujols was too squat and nonathletic to play major league baseball—a bad-bodied kid whose physique would overwhelm his natural hitting ability.
And that’s how it usually works with squishy-thighed 20-year-olds, but the pudgy, line-drive machine from Independence, Missouri, never stopped hitting. He batted .314 in his only minor league season and lapped the rest of the field in his march to the 2001 NL Rookie of the Year award.
Now the three-time MVP owns one of the richest contracts in baseball history and a place among the game’s greats.
14. 2006 St. Louis Cardinals
Cardinals fans who think last year’s team was the ultimate long-shot champion have a mighty short memory.
The ’06 Red Birds went just five-games over .500 during the regular season and featured one of the decade’s worst playoff rotations. Chris Carpenter and Jeff Suppan were its only members to post an ERA-plus over 100. Jason Marquis earned 33 starts despite a 6.02 ERA and a 1.28 SO: BB ratio.
It was ugly, and there wasn’t much reason for optimism heading into an NLDS matchup with the San Diego Padres.
After a four-game upset, the odds only got longer. Now St. Louis was up against the 97-win Mets, a team that finished nine games ahead of the NL’s next best squad.
But again the Cardinals were up to the challenge, pushing New York to a seventh game and winning in dramatic fashion as Adam Wainwright froze Carlos Beltran with an 0-2 hook.
Perhaps the more impressive triumph was their 4-1 whitewashing of a talented Tigers team in that year’s World Series, but posterity favors dramatics. And for dramatics, there were few scenes more stirring than the stone Wainwright hurled to slay an NL Goliath.
13. 1990 Cincinnati Reds
Behind the colorful and powerful bullpen trio of Norm Charlton, Rob Dibble and Randy Myers—dubbed the “Nasty Boys”—Cincinnati’s presence in the 1990 World Series seemed gratification enough.
The team was just a year removed from a fifth-place finish, and most folks figured the juice from their 4-2 NLCS upset of the Pirates was bound to dry up.
The Oakland A’s were just too powerful—defending World Champions and the owners of 12 more regular season wins than the upstart Reds. The tea leaves read “sweep.”
And the tea leaves, as always, were right, except it was the Reds doing the sweeping. Against a locked-in Reds staff and, of course, the always-suffocating bullpen, Oakland didn’t score a run after the third inning in any of the four games.
12. Tim Wakefield
Tim Wakefield went through a lot of crap just to get released
Pittsburgh drafted the Florida Tech product as a first baseman in 1988, but it became clear early that Wakefield was no Lou Gehrig. Surprise, surprise, 21-year-olds hitting .189 at Low A aren’t a hot commodity.
So Wakefield figured he’d give pitching a try, riding his singular knuckleball all the way to Pittsburgh and a spot in the Pirates rotation.
But before he could get comfortable there the player’s strike hit and, upon resolution, the Pirates released Wakefield. The novelty, I suppose, had worn off.
That was 1995.
Seventeen years later, at age 45, the desperate kid with the gimmick pitch has finally left baseball. He has an even 200 wins to his name.
11. Tommy John
Today it seems more science than magic, but isn’t that the way of most tall tales? Just another sign of human progress, my friends.
Back in the 1970s it was pure fantasy to suggest that a lame-armed pitcher could resurrect his career by replacing a torn elbow ligament with a ligament from elsewhere in his body. It was the surgical equivalent of a glass-slipper search.
But it worked, and Tommy John went on to win 164 games after his Frankenstein patch-up job.
10. The 1991 World Series
To approximate the likelihood that the Atlanta Braves and Minnesota Twins would meet in the 1991 World Series, take the probability of a Jaguars-Rams Super Bowl in 2012—and then triple it.
Because crazy stuff like this never happens in the 162-marathon that is the Major League Baseball season.
And yet it did.
The Braves were fresh off six consecutive losing seasons, each of which saw them finish either fifth or sixth in their six-team division.
The Twins had been in a full-on nosedive since their 1987 championship, bottoming out in 1990 with a last-place finish in the AL West.
Then the tables turned—or maybe they flipped. The Braves rode baby aces Tom Glavine, John Smoltz and Steve Avery to a 29-win improvement. In the NLCS they clipped the heavily favored Pirates in a seven-game thriller.
The Twins rode a resurgent offense to a 21-game turnaround of their own, sliding past the Toronto Blue Jays in a five-game ALCS win.
When fairy tale met fairy tale in the World Series, predictable levels of madness ensued.
Kirby Puckett hit a walk-off home run in the 11th inning of Game 6, inspiring Jack Buck’s famous “we’ll see you tomorrow night” call and setting up a decisive seventh game. Once there, the Twins would seal the franchise’s third championship behind 10 shutout innings from Jack Morris and walk-off base hit by Gene "Don't call me Barry" Larkin.
9. Pete Gray
At age six Pete Gray slipped under a train and lost his right arm.
It would have been the end of his baseball career if not for his abundant athleticism and the intercession of a world war.
To compensate for the loss, Gray developed a capable one-handed swing and a nifty maneuver through which he would catch the ball, pin his mitt against his right side and remove the ball in an almost seamless, singular motion.
Gray became so adept at the sequence that he found work with various semi-pro teams through the early 1940s. In 1945, when many of the best players were at war, the St. Louis Browns purchased his contract and gave him a regular run as an outfielder.
Given his limitations, Gray’s play was an inspiration. Over 77 games he hit .218 and struck out just 11 times.
8. Josh Hamilton
From “Super Natural,” Albert Chen’s 2008 profile of Josh Hamilton for Sports Illustrated:
During his darkest hours—after he had been banished from baseball in 2004 and was doing coke, downing a bottle of Crown Royal a day and burning through his entire $4 million signing bonus—Hamilton had recurring dreams that he was 'fighting the devil, an awful-looking thing,' with a stick or a bat, swinging but always missing.
If that was the valley, then here are the peaks:
Four All-Star game appearances, the 2010 MVP award, a two-run home run in Game 6 of the World Series and that summer night in the House that Ruth Built, when he made the single most difficult task in sports look impossibly easy.
7. John Hiller
On January 11, 1971, 27-year-old John Hiller suffered three heart attacks.
The man who had pitched 104 innings for Detroit the year prior and helped lead the Tigers to a world championship in 1968 barely survived.
In the aftermath, doctors performed intestinal bypass surgery in order to suppress his weight. The procedure worked, and as Hiller shed pounds, he envisioned another day on the hill.
In July of 1972 he completed the comeback with a three-inning relief appearance against the Chicago White Sox. Over the season’s second half he worked 44 innings, posted a 2.03 ERA and even won a game in that year’s ALCS.
It gets better.
Fully healthy in 1973, Hiller would turn in the finest year of his career. He saved a then-record 38 games and posted an absurd 286 ERA-plus. He won awards for both Comeback Player of the Year and Reliever of the Year.
Though he would never match those highs in any of his subsequent seven seasons, he remained well above average for the next three years and effective into his late 30s. Longevity would become a defining characteristic of his career, a word the must seem like a blessing in the context given.
6. Bill James
The revolution started on the night shift—those idle hours security guard Bill James would spend forming obscure questions about baseball.
Harvesting data available through common box scores, James sated his many curiosities and published the results to any who would hear him. In the beginning, there weren’t many, maybe a few hundred.
But from a hundred grew a thousand, and then 10,000, each new seat of ears captivated by James’ exotic statistics, cunning prose and against-the-grain perspective.
Thirty years later the revolution has reached baseball’s highest levels. And it isn’t just a Billy Beane thing. The theories and numbers created by James and his disciples influence decision making in every MLB front office.
Whether or not you agree with the principles, there is no disputing their import.
5. 1906 Chicago White Sox
What follows is not a misprint.
The 1906 Chicago White Sox hit .230 with seven home runs—as a team.
Behind a stellar staff, they managed to win the American League pennant and draw a showdown with the crosstown Cubs—a team that went 116-36 and still holds the all-time mark for best winning percentage.
The Pale Hose were expected to fall hard against a squad that featured four future Hall of Famers.
They didn’t, capping a remarkable upset with consecutive eight-run outbursts in games five and six.
For the entire 1906 season, they scored that many runs just 14 times.
And their starting third baseman hit .183. And they had a player-manager named Fielder Jones.
Fielder Allison Jones was the man’s God-given name—like some sort of progression from weird name to normal name in three parts.
OK, I’m done now.
Forays into turn-of-the-century baseball are just the best.
4. Mike Piazza
With the 1,390th pick in the 1988 amateur draft, Dodgers manager Tommy Lasorda put baseball interests aside and selected a non-prospect out of Miami-Dade Community College named Mike Piazza.
Piazza’s father, Vince, was a childhood friend and the ensconced Dodgers head man said he’d pick the kid as a friendly gesture.
Good move, Tommy.
Mike Piazza would go on to make 12 All-Star appearances, win 10 Silver Sluggers and retire as perhaps the greatest hitting catcher in baseball history.
3. Lou Brissie
Lou Brissie was lucky to escape December 2, 1944, with his life.
It was a day of heavy fighting in the Italian Mountains, punctuated by an infernal blast. The shell killed eight men and shattered Brissie's left leg.
Amputation seemed the most likely course, but Brissie begged for his limb. Twenty-three major operations later, Brissie had his wish. And he could walk again, albeit with a metal rod in his leg.
A promising southpaw before his tour in World War II, Brissie figured he’d give baseball a try upon returning home. He’d already beat the war, so why the hell not?
Even with a left leg that was now an inch shorter than the right, Brissie discovered his fastball still had life. So much life, in fact, that Brissie earned a promotion to the Philadelphia Athletics in 1947. The following year he went 14-10 with a 4.13 ERA. A year later he made his first and only All-Star appearance.
In all, he lasted a remarkable seven seasons at baseball’s highest level.
2. 1969 New York Mets
The Mets winning the World Series in 1969 was about as preposterous a proposition as putting a man on the moon.
So much for impossibilities.
In their first seven seasons the Mets never finished higher than ninth place—out of 10. That is until 1969, when pitching luminaries Tom Seaver and Jerry Koosman—with an assist from a young gunslinger named Nolan Ryan—led New York to an out-of-nowhere 100-win campaign.
Come postseason, most folks still weren’t buying it.
Because of recent history and a line-up that featured just one regular over .280, the Mets came into their showdown with the Baltimore Orioles as heavy underdogs. Five games later they were world champions, etched into baseball lore as the endearing, alliterative “Miracle Mets.”
1. Babe Ruth
Perhaps it is redundant to re-tell Babe Ruth’s life story, one so woven into the fabric of American mythology that it feels like a shared memory.
Then again, it would be irresponsible to exclude his name and his legend on a list purporting to exposit the game’s greatest Cinderella stories.
So, for accuracy’s sake, here goes:
George Herman Ruth came of age in a Baltimore orphanage, dispatched there by a father that had little time or money for child rearing. The priests there introduced young George to baseball, and he took an immediate liking to the sport.
Ruth’s greatest strength was his powerful left arm, which drew attention from scouts of the then-minor league Baltimore Orioles. After a short stint there, the Orioles traded his rights to the Boston Red Sox, whereupon he would become one of the game’s best left-handed pitchers over the next four seasons.
Had the story stopped there, it would have been a remarkable one.
Of course, it didn’t.
Ruth transitioned to the outfield, became the greatest hitter in league history, revived the New York Yankees, built a figurative house, prompted the game’s most important rule change, created modern celebrity and jumpstarted the golden age of professional sports.
Not bad Georgie boy, not bad at all.