MLB's 25 Craziest 'Rollercoaster' Careers Ever

Start with the roller coaster—a whirling dervish of a ride that careens up, down and side to side with seeming impunity.

"Hey," someone once thought, "what a great metaphor for instability."

And so one million usages later we've arrived here—the 25 most up-and-down careers in baseball history.

There are no hard and fast qualifications for this list. Just know that the typical career arc won't cut it.

Carlos Zambrano

The winding road of Carlos Zambrano's career has at least one more turn in it.

Miami, hold your breath.

The newest Marlin wore many hats during his eleven years in Chicago: ace of the future, ace of the present, overpaid, clubhouse cancer, workhorse, injury prone.

The labels, it seemed, rotated with the days of the week and ended with the club suspending him for the final two months of his Cubs career.

His extensive rap sheet includes fights with teammates (Michael Barrett, Derrek Lee), fights with opponents (Jim Edmonds), off-field controversies (belligerent comments about Cubs fans), on-field blowups (RIP Gatorade cooler) and a faux retirement.

As Zambrano unites with notorious hot-head Ozzie Guillen under the South Florida sun, we're left to wonder: Is the craziest yet to come?

Tony Conigliaro

If you're looking for a buzz kill, run a quick internet search on Tony Conigliaro.

And bring tissues.

Born in the Boston suburb of Revere, Massachusetts and raised in the city proper, Conigliaro broke in with the hometown Red Sox at 19 years old.

He hit 24 home runs and batted .290 during his rookie season and followed that up with a league-high 32 home runs in his sophomore campaign.

Midway through his fourth season, which was shaping up as his best year yet, the Angels' Jack Hamilton beaned Conigliaro in the face, forever altering the rocket-ship trajectory of his career.

The resultant injuries, which included a damaged left retina, caused Conigliaro to miss the rest of the 1967 season and all of 1968.

He made a heroic return in 1969 and mustered two solid seasons, but the triumph was short-lived. Conigliaro's eyesight continued to degenerate and, in an ironic twist, the Red Sox traded him to the Angels before the '71 campaign.

After 74 games with the Halos, Conigliaro retired. He attempted another comeback with the Red Sox in 1975 but lasted just 57 at bats.

Like a boxer off the mat, Conigliaro took one last shot at a career in baseball during the early 1980s, this time as an announcer.

That too was cut short when he suffered a heart attack. Reduced to a vegetative state for the rest of his days, Conigliaro died in 1990 at age 45.

Dick Allen

Surprising as it felt, Dick Allen's MVP season in 1972 didn't come out of nowhere.

He was, after all, a Hall of Fame-caliber hitter in the prime of his career coming off eight consecutive seasons with an OPS+ over 140.

The surprise? He was playing for his fourth team in four years.

Therein lies the turbulence of Dick Allen's career—an uncommonly great hitter dogged by persistent personal conflicts.

Allen got his start with the Philadelphia Phillies, a franchise known for its hostility toward black players.

Allen outplayed the prejudice, and in 1964, he became the second player in franchise history to win the Rookie of the Year award.

Allen's success didn't meet with admiration from the Philadelphia faithful. Known for his habitual lateness and short temper, Allen earned a reputation as a malcontent and soon found himself the target of both boo birds and batteries.

The dystopian relationship between Allen and the organization culminated in a trade to the Cardinals when Allen was just 28.

(Side note: The Phillies were supposed to receive Curt Flood in the trade, but Flood refused, instead seizing the moment to challenge baseball's reserve clause and eventually clear the path toward free agency.)

Allen no doubt had a surly streak, but the breakup was as much a sign of the times as it was an indictment of Allen's behavior.

As Bruce Markusen put it in an article for The Hardball Times:

"

"Some of Allen’s problems were self-inflicted; others were created by a 1960s American culture that was still plagued by deep-seated racism and segregation."

"

Racism, of course, wasn't exclusive to Philadelphia. Allen's strong personality stirred trouble elsewhere, and he lasted in St. Louis just one year. After a season in Los Angeles, Allen ended up with the White Sox, where he turned in the finest year of his career and captured the AL's top prize.

The MVP glow didn't last long, and a conflict with Ron Santo precipitated his trade back to Philadelphia in 1975.

In was perhaps the oddest twist of all—the team that once banished him to a life of baseball transience welcomed him back as a prodigal son.

Allen played a support role on a '76 Phillies team that won 101 games before retiring with the Oakland A's in 1977.

George Steinbrenner

Though he never played an inning, George Steinbrenner inspired enough opinion—good and bad—to merit inclusion on this list.

"The Boss" began his Yankees ownership as something of a knight in shining armor, rescuing the hallowed club from fiscal insolvency brought about by the previous owners. In Steinbrenner's first decade as owner, the club made four World Series and won two championships.

The good times ended in the mid-1980s, as Steinbrenner gained a nasty reputation for his meddlesome ways and the Yankees missed 12 consecutive postseasons. The irascible head man hit rock bottom in 1990 when commissioner Fay Vincent suspended Steinbrenner for his role in a plot to defame Dave Winfield's character. 

(For a pop culture expression of Steinbrenner's nadir, I refer you to his depiction in Seinfeld.)

Then the Yankees dynasty of the late-90s happened, and Steinbrenner, like his team, rose from the ashes.

Upon his death in 2010, New Yorkers feted Steinbrenner as a model owner and many called for his induction to the baseball Hall of Fame.

It was a conspicuously glowing reception for a man once subject to intense scrutiny.

Gary Sheffield

Gary Sheffield played for eight franchises in his 22 seasons, none of them for more than four years.

Great as Sheffield was, those numbers tell the story of his career.

Moments of great triumph—batting title, World Series win, nine All-Star appearances—felt fleeting in the face of his nomadic ways.

Abetted by a toxic tongue, Sheffield managed to thrill and repulse fans at each of his big league stops. Ultimately it would overshadow his 500 home runs and lead him down a path few of his talent ever walk.

Roger Clemens

The many faces of Roger Clemens' career:

• Red Sox prodigy
• Red Sox legend
• World Series goat
• Red Sox turncoat
• World Series champion
• Ageless wonder
• Steroid user
• Accused felon

And that's just what we know now.

Even in retirement, Clemens' legacy is being written and re-written. To some he is the greatest right-handed pitcher of the modern era. To others he is the very definition of athletic hubris, the disgraced face of baseball's darkest era.

Take any number of angles on Clemens' career, but know that none of them tell the whole story.

Rick Ankiel

After a decade in professional baseball marked by uncertainty, Rick Ankiel has found his place in this league. He's a decent fourth outfielder, the final middle ground for a man who could have been so much more and came close to being so much less.

So how did we get here?

Rick Ankiel began as one of the game's great pitching talents. He debuted at age 19 and Baseball America rated him the number one prospect in the league heading into the 2000 season.

That year, Ankiel went 11-7 with a 3.50 ERA and 10.0 K/9. He was just 20 years old.

Then the great collapse.

In his first career playoff start, Ankiel walked six and threw five wild pitches in 2.2 innings of work.

His control never returned.

After three seasons spent searching in the minor leagues, Ankiel abandoned the mound and attempted a comeback as a position player.

It worked, surprisingly well. Ankiel flashed big time power during a 2005 season split between A and AA, and after missing 2006 due to injury, made the Cardinals as a call-up in 2007.

His big league return was the feel-good story of the year, until it wasn't.

A steroid accusation threw another wrench in Ankiel's confused baseball career and threatened to derail his comeback. The Cardinals stood by him, and he turned in the best year of major league career in 2008.

But this time, instead of flaming out or rising up, Ankiel plateaued. He regressed to replacement-player levels and settled into a new role as a journeyman outfielder.

A story that fluctuated between extremes had its surprisingly mundane conclusion.

Eddie Waitkus

Gather 'round injured athletes wallowing in self-pity and listen to the tale of Eddie Waitkus.

Trust me, whatever your ailment, it does not compare with what Eddie Waitkus overcame in the summer of 1949.

That year a female fan named Ruth Ann Steinhagen, distraught over Waitkus' trade from the Cubs to the Phillies, shot the first baseman at close range in the latter's hotel room.

If that sounds familiar, it's because Bernand Malamud borrowed parts of Waitkus' tale for his novel, The Natural.

Somehow Waitkus survived the attack and recovered in time for the 1950 season. He played 154 games, a career-high, and helped Philadelphia's Whiz Kids capture their first NL pennant since 1915.

But early returns were deceiving, and the emotional residue of the incident haunted Waitkus. He scuffled through five more big league seasons and suffered from post-traumatic stress until his death in 1972.

(Big ups to http://www.sbeen.com for the wonderful bio.)

Matt Bush

Drafted first overall by his hometown San Diego Padres in 2004, Matt Bush has died a million baseball deaths all before even making the major leagues.

Start with an inauspicious beginning.

Before he'd played a single inning, the Padres suspended Bush for his involvement in an altercation at an Arizona nightclub. Once cleared of that mess, Bush posted an abysmal .192 batting average in his first professional season.

Things never got much better, and by 2007 the Padres had seen enough. They converted Bush into a pitcher and prayed for a transformation. Bush obliged, for a bit, striking out 16 batters in first 7.2 innings.

He then promptly tore a ligament in his pitching elbow and, while rehabbing, ran afoul the law once more.

The Padres released Bush. The Blue Jays signed him. He violated team policy. The Blue Jays released him.

Today, Bush is a member of the Tampa Bay Rays organization and posted a promising 13.8 K/9 over 50.1 innings last year in AA Montgomery.

He is 26 years old.

Ellis Valentine

Watch the above video and you'll see why 25 years after his big league career ended, people still talk about Ellis Valentine.

Dude could chuck it.

Blessed with perhaps the greatest outfield arm in baseball history, Valentine reached the major leagues by 20 and was an everyday player by 21.

Valentine, Gary Carter and Andre Dawson made up the core of a promising young Montreal Expos team that won more than 55 percent of their games each year from 1979 to 1981.

For his part, Valentine topped 20 home runs three times and finished 1978 with a 5.1 WAR.

But as Dawson and Carter ascended, Valentin faltered. Drug addiction was the rumored cause of his fading power, and midway through an abysmal 1981 campaign, the Expos traded him.

He appeared to find some traction in 1982, but the resurgence proved fleeting.

Valentine missed the entire 1984 season, and a comeback attempt with the Texas Rangers in 1985 ended when a pitch broke Valentine's jaw.

Darryl Strawberry

Darryl Strawberry leaves us two lenses with which to view his career.

1.) Elite talent who, due to substance abuse and personal indiscretions, inexplicably hit just 17 home runs between 1992 and 1995.

2.) Rookie of the Year, eight-time All-Star who topped topped 20 home runs ten times and re-invented himself as a useful role player on three Yankees championship teams.

His last days in uniform put those contradicting accounts of his legacy into perspective.

In 1998 doctors diagnosed a 36-year-old Strawberry with colon cancer. In recovery, he vowed to play again.

His comeback hit a snag when Tampa police arrested him for solicitation and cocaine possession. Major League Baseball suspended him 140 games for the incident.

Strawberry was re-instated for the postseason, when his crucial three-run homer propelled the Yankees to the ALCS. There they would best the Red Sox and eventually roll to their third title in four years.

Still under suspension, Darryl Strawberry retired that offseason as a four-time World Series champion.

So was Darryl Strawberry a...Survivor? Deviant? Champion?

Yep.

Fred Merkle

How hard would it suck to live the rest of your life defined by a mistake you made as a teenager?

Welcome to Fred Merkle's world.

During the 1908 pennant chase, Merkle—who was 19 and the youngest player in the NL at the time—failed to touch second base on play where his Giants otherwise would have won the game. The gaffe, heretofore known as Merkle's Boner, led to a Giants loss and ultimately cost them the pennant.

It was the first of many letdowns in the young first baseman's career. He appeared in five World Series, never won and, more poignantly, never outlived the infamy of his welcome-to-the-big-leagues moment.

Adding a twist to his star-crossed career, Merkle played five years in the International League after the Cubs released him in 1920. He stuck around long enough to get another shot at the major leagues, this time with the Yankees.

His second go-round was less notable than the first, but no more fruitful. Impressive as it was to play in the majors after a five-year intermission, Merkle lasted only seven games.

Dwight Gooden

I look at Dwight Gooden's statistics and they shock me.

How could a pitcher that felt like such a flame out have lasted 16 seasons?

At 20, Gooden was the best pitcher in baseball. He posted a 229 ERA+, led the league in strikeouts and won his only Cy Young award.

America remembers the rest of his career as a self-inflicted fall from glory, abetted by drug use and arm injury. Or as Sports Illustrated put it in a 1993 cover article, "From Phenom to Phantom."

The truth is a bit less clear. Gooden's was more of a slow slide to mediocrity, one the saw him post decent numbers well into his third decade.

Josh Hamilton

Josh Hamilton's wild ride is already the stuff of baseball legend.

Things you already knew about Josh Hamilton because you don't live under a rock.

• The Tampa Bay (Devil) Rays drafted Hamilton first overall in 1999.
• Drug addiction force him out of baseball and he spent 2004 to 2006 on the sidelines.
• The Cubs selected Hamilton in the 2007 Rule 5 draft and traded him to the Reds.
• The Reds wasted no time promoting Hamilton to the senior club, where he posted a 131 OPS+ in 90 games.
• The Reds traded him to the Rangers where he put on the greatest display in home run derby history and won the American League MVP.

Recent revelations of an alcohol relapse provide an unfriendly reminder that one of the most improbable stories in baseball history remains incomplete.

Manny Ramirez

Because the world cannot process Manny Ramirez's eccentricities, we've developed a crutch: Manny being Manny.

How else to describe the man who has done the following?

Hit 555 home runs, twice violated MLB's drug policy, led the league in slugging and OBP three times, weaseled his way out of Boston, endeared himself to Los Angeles, weaseled himself out of Los Angeles, disappeared into a wall mid-game and set new standards for defensive indifference.

Ramirez continues to divide fanbases the league over, perhaps the inevitable conclusion of a controversial career that spanned 22 years and five cities.

Reggie Jackson

Reggie Jackson made it as easy to love him as it was to hate him.

Which is to say both came easy.

Fans adored Jackson for his mammoth home runs, his brazen assurance and his clutch October performances.

They hated him with equal vigor for his king-sized whiffs, his lack of hustle and his outsized ego.

Remember, this was the man to whom the following quotes were attributed:

"After Jackie Robinson the most important black in baseball history is Reggie Jackson, I really mean that."

"I didn't come to New York to be a star, I brought my star with me."

"Fans don't boo nobodies."

And, of course:

"I'm the straw that stirs the drink."

As the parlance of the times would put it, if you dug the swagger, you dug Reggie Jackson. If you didn't, his 563 career home runs probably passed you by.

Dock Ellis

Most famous for pitching a No Hitter while on LSD, Ellis' career had no shortage of delicious anecdotes.

There was the time a security guard at Riverfront Stadium maced Ellis, and the time he once threw at every member of the Reds lineup in retaliation.

There was the time he called Texas manager Billy Hunter "Hitler," and the time he collaborated with future U.S. Poet Laureate Donald Hall on a revealing book about baseball and society.

And just when it seemed his time was up after an injury-plagued 1975 season, Ellis re-emerged with the Yankees in 1976 and won AL Comeback Player of the Year. He parlayed that success into three more seasons, two of which saw him play for three different teams in a single year.

Through it all, Ellis remained outspoken and independent. Twelve seasons, five teams and one remarkable career.

Lenny Dykstra

Lenny Dykstra's roller coaster career flows so seamlessly into his roller coaster retirement that there seems no point in separating the two.

As a player, Dykstra's non-stop motor both made his career and, in a sense, undid him. Nails' relentless drive became the foundation for a 12-year career in the major leagues that saw him play in two World Series and lead the NL twice in hits.

The same reckless abandon caused him to party his way out of New York, wrap his car around a tree during his time with the Phillies and succumb to injuries in his early 30s.

Much of the same could be said of Dykstra's post-baseball turn as an entrepreneur. It started with the typical Dykstra bang—he was lauded by "stock guru" Jim Cramer for his business acumen and varnished with praise for his aggressive deal-making—but the internal mechanics proved faulty.

Dykstra's business ventures have since gone belly-up and he's wallowed in personal controversies ranging from sexual harassment to prostitution to grand theft auto.

Dave Winfield

From phenom to superstar to scapegoat to legend, Dave Winfield inspired more controversy than seems possible for a man of his disposition.

The relaxed, genteel Winfield featured on Baseball Tonight doesn't look the part of a lightning rod athlete. And yet at some point in his career, by grace of coincidence, expectation and George Steinbrenner, he was just that.

Start with the phenom bit.

A baseball and basketball star at the University of Minnesota, Winfield was the only athlete in American sports history drafted by four sports leagues (MLB, NBA, ABA and NFL, even though he didn't play college football). He chose to sign with the Padres, who drafted him fourth overall with designs on having him pitch.

They quickly changed course, and promoted him directly to the Major Leagues as a right fielder. There Winfield would stay, quickly growing into of the game's best outfielders. Over eight years in San Diego, Winfield made four All-Star teams and twice finished top ten in the MVP voting.

Before the 1981 season, Winfield signed with the New York Yankees for a then-record 10-year, $23 million contract. Bitter over the money he'd spent to lure the big fish free agent, Yankee owner George Steinbrenner took an almost immediate dislike to the easy-going Winfield.

Though Winfield made the All-Star game in each of his eight seasons with the team, Steinbrenner targeted him time and again for his perceived failures in the clutch and the fact that the Yankees never won a World Series during his tenure.

So vicious was Steinbrenner that he hired reputed mobster Howie Spira to sleuth around Winfield's personal life in pursuit of compromising information. The scandal resulted in Steinbrenner's two-year suspension from baseball.

Meanwhile, Winfield's Yankee career ended in ignominy. He sat out the entire 1989 season due to a back injury and New York traded him to the Angels midway through the 1990 campaign.

In Southern California, Winfield was rejuvenated, thus beginning a sparkling end-of-career run that earned him AL Comeback Player of the Year in 1990 and that elusive World Series title as a key member of the 1992 Toronto Blue Jays.

It was a graceful exit for a man who spent much his prime dragged through the muck.

Dave Parker

Never even, always interesting, Dave Parker lived many baseball lives over his 19-year career.

He started as a sensation, breaking in with the Pittsburgh Pirates at 22 and posting five .300+ seasons from 1975 to 1979. Before the fifth, Parker became the first professional athlete to sign a contract worth $1 million per annum.

He looked, to most, like a legend in the making.

Raised compensation and expectation conspired to undo Parker. His weight ballooned, he fell victim to injuries and developed a cocaine habit. All of the above led to a noticeable drop in performance, accompanied by the ire of Pirates fans (who once showered him with nuts and bolts).

When he signed with the Reds in 1984, Parker had the look of a broken man.

Then came the revival. Parker's average crept back toward career levels in '84, and he followed that up with a 1985 season second only to his MVP year in 1978.

Established once again as a superstar, Parker enjoyed four productive years in Cincinnati before downshifting into the final phase of his career.

Parker signed with Oakland in 1988 and helped lead the team to back-to-back World Series appearances, the latter of which resulted in Parker's second title.

Dennis Eckersley

There's almost too much outlier in Dennis Eckersley's career to comprehend.

He won 20 games in a season. He saved 50 games in a season. He won the Cy Young and the MVP in the same year. He walked a combined seven hitters between 1989 and 1990. He served up Kirk Gibson's legendary World Series home run. He won a World Series the very next year.

It was a career of stunning peaks and valleys, but one where the valleys seemed to inadvertently open doors to better things.

When Eckersley's wife left him for Cleveland teammate Rick Manning, the club traded him to Boston. There Eckersley had his best years as a starter and twice finished among the top ten in Cy Young voting.

In later years, his alcoholism accelerated his decline as a starting pitcher and forced him to take on work as a reliever. Soon he was the most dominant relief pitcher of his era.

Usually divorce and alcoholism don't beget such riches.

A long, strange trip for the man with the long, strange hair.

Jimmy Piersall

In posterity, Jimmy Piersall's antics lose their impish charm and nostalgic color.

Piersall brawled with teammates, fought fans and famously ran the bases facing backward after a home run. He even claimed to conversations with the Yankee plaques in Monument Park.

Piersall also suffered from bi-polar disorder, a disease that made his professional behavior anything but.

Piersall went public with his illness in the mid-1950s, at a time when such admissions were rare. The public reckoning inspired a movie based on Piersall's life and turned the Red Sox center fielder into a star.

It did not, however, bring Piersall much peace. Erratic behavior continued throughout a career that saw him bounce between five teams over his final decade.

Smoky Joe Wood

Red Sox legend Smoky Joe Wood started young and started fast. Between ages 19 and 25, the right-handed fireballer put together one of the greatest stretches in pitching history, posting .678 winning percentage and a 1.98 ERA.

Though the statistics didn't reveal it, Wood pitched the last three seasons of that run in immense pain. A broken thumb suffered in 1913 curbed his durability and eventually led him to miss most the 1916 and '17 seasons.

He re-emerged in 1918 with the Cleveland Indians, this time as an outfielder. He hit well enough to play parts of six seasons as a position player, and helped the Tribe to a World Series title in 1920.

Even more remarkable, Cleveland called on him to pitch relief several times during his Indians career even though Wood was years removed from his time on the mound.

Wood retired at 33, with a fascinating 14-season journey through the big leagues to his name.

Babe Ruth

Babe Ruth's story doesn't need re-telling.

But for the purposes of this list we must re-iterate: Babe Ruth began as a great pitcher, picked up hitting midway through his career, moved to the Yankees in the most famous trade in sports history and, through the sheer magnitude of his talent, changed the trajectory of both his franchise and his sport.

Then it ended, rather suddenly really, with a hobbled Ruth playing out the string in a Boston Braves uniform.

That botched farewell was the final touch of surprise on a career framed by the improbable.

Alex Rodriguez

For his obscene contracts, admitted steroid use and celebrity dalliances, Alex Rodriguez has become baseball's resident anti-hero.

But it wasn't always that way. Or perhaps I should say, it isn't always that way.

This is the man, for instance, who led the league in hitting his first full MLB season, had two MVP campaigns where he led the AL in home runs, slugging percentage and OPS and overcame his postseason bugaboo with a spectacular 2009 performance.

And at those moments, fans stood stunned, expressing a sort of tacit admiration for the great A-Rod.

At the very least, they stood in awe of his talents.

Such is the power of great players. No matter how despicable, they are always a moment away from transcendence.