10 Players The New York Yankees Gave Up On Too Soon (And 10 They Kept For Too Long)

The New York Yankees are one of the most storied franchises in professional sports history. Beneath the microscope of New York City’s spotlight, with its large population and centralization of major media outlets, the team is small slice of Americana as the big apple’s foremost representatives of the national pastime. By and large, the Yankees organization has been up to the task. They’ve accumulated World Seriew Championships across multiple generations. Moreover, in a team sport, they boast a roster of truly iconic star players that more than holds its own against any team. The Bronx Bombers have names attached to their history like Babe Ruth, Mickey Mantle, Joe DiMaggio, Lou Gehrig, Toget Maris, Billy Martin, Yogi Berra, Bernie Williams, and Derek Jeter to name just a handful.

For all of the legends who’ve taken up residence and plied their trade at Yankee Stadium, there, are of course, some less luminous figures who’ve been associated with the team. There’s no exact science to managing a baseball team roster, and no crystal ball to prognosticate a player’s destiny. In hindsight, though, we can recognize mistakes. Some are the great what-if figures whom management traded or waived before they wound up realizing their considerable potential and becoming stars. Others are players the team afforded too many opportunities, or kept well past their shelf life until they were past their prime.

This article takes a look at ten key players the Yankees said goodbye to too soon, and ten whom the team should have been more patient and held onto.

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20 Gave Up Too Soon: Hideki Matsui

AP Photo/Kathy Willens

As a New York Yankee, outfielder Hideki Matsui won a World Series and was a two time All Star. 2009 saw him reach the pinnacle of his career in pinstripes, not only helping his team to a Championship, but becoming the first Japanese player to earn World Series Most Valuable Player honors in the process.

You’d think the Yankees would make ever effort to hold onto Matsui, but they instead allowed him to slip, leaving New York to sign with the Angels.

The man was a fan favorite and a proven winner and it was a big mistake to give up on him prematurely.

19 Kept For Too Long: Alex Rodriguez

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Alex Rodriguez was one of the biggest baseball stars of his generation whose resume included fourteen All Star appearances and three American League MVP awards. His career stretched twenty two seasons, and while fans can respect his longevity, his years playing comes with the caveat that this body and skills deteriorated over time.

A-Rod’s less than clutch play during most post seasons, and rumors of his big ego meant he was rarely looked at as a favorite of teammates or fans. He spent over a decade with the Yankees which was probably too long for this unhappy marriage.

18 Gave Up Too Soon: Anthony Swarzak

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Anthony Swarzak joined the Yankees as a promising young talent, expected to thrive as a middle relief pitcher. However, his time in pinstripes is widely regarded as a disappointment. He flopped in most major performances, with some suspecting that he couldn’t handle the New York spotlight.

Swarzak’s fortunes would turn, though, when he joined the Toronto Blue Jays and showed signs of life. From there, he signed as a free agent with the Chicago White Sox where he broke out as a star pitcher. Maybe New York wasn’t the right fit for Swarzak, but there’s also the possibility he just needed more time to settle into MLB play, and the Yankees let him go too soon.

17 Kept For Too Long: A.J. Burnett

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AJ Burnett enjoyed a lengthy career at the mound in Major League Baseball, assembling a respectable career across teams including the Pittsburgh Pirates, Philadelphia Phillies, Toronto Blue Jays, and Florida Marlins. He was a Yankee, too, and even a part of the team’s 2009 Championship run. However, rather than a key cog in the machine, he’s generally remembered as a guy who never panned out in the Bronx.

Burnett commanded a big salary, but his results were far less consistent than his paychecks would suggest.

While he had his moments, by the end of three full seasons with the team, he was overdue for a change of scenery.

16 Gave Up Too Soon: Carlos Beltran

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Carlos Beltran has played with seven different teams which may suggest to the casual observer that no one wants him for long. However, he’s a clutch player whose performances have earned him the nickname Mr. October.

Beltran’s tenure with the Yankees was checkered, starting with missing significant time due to injuries and personal issues. The next season and a half didn’t show his best side either, but in 2016 he did begin to gather steam—just in time for the Yankees to trade him to the Texas Rangers. Beltran would ultimately sign with the Houston Astros the following year, and its telling that he helped them to a World Series Championship. Maybe if New York had been a big more patient, he might have helped them to a similar fate.

15 Kept For Too Long: Phil Hughes

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Phil Hughes started his professional baseball career with the New York Yankees and the team invested a lot in him and his star potential. While a number of Yankees have suffered from short trial periods and management giving up on them too soon, Hughes benefited from opportunity after opportunity, playing a total of seven seasons with the team.

Unfortunately, Hughes never lived up the lofty expectations attached to him, and seven seasons wound up feeling like an eternity to keep this guy on the mound. By the end of that 2013 season, he was taken out of the rotation and the writing was on the wall that the Yankees had finally lost patience with him.

14 Gave Up Too Soon: Chris Carter

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Free agent Chris Carter looked like a big time acquisition for the New York Yankees when they signed him for the 2017 season, coming off of a monster year with the Milwaukee Brewers. Carter struggled mightily upon his arrival in New York, however, and was waived at the mid-season mark.

To be fair, the Yankees management can’t be accused of waiting too long or throwing good money after bad in this particular case.

However, after Carter’s big season just a year earlier, there’s a very real argument that they simply should have given him more time to progress to see if he might have settled in with the Bronx Bombers.

13 Kept For Too Long: Jacoby Ellsbury

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You can’t necessarily blame the New York Yankees for signing Jacoby Ellsbury to a big money, multi-year deal after broke out as a star for the rival Boston Red Sox. Long term contracts are a good way of securing a player’s loyalty and making big investments on younger talent that may well blossom further.

Unfortunately, the center fielder hasn’t dazzled the Bronx crowd. On the contrary, all indications are that he may have peaked in Boston. To make matters worse, while he’s missed most of this season due to back problems, the Yankees have been just fine without him, suggesting that, five years into his tenure with the team, he’s overdue for a change of scenery.

12 Gave Up Too Soon: Curtis Granderson

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Curtis Granderson proved himself nicely over the course of four seasons with the Yankees. While that last season got cut short due to injury, he otherwise starred for the team as both an offensive threat and a tremendous fielder.

Instead, the Yankees let him go. Granderson has gone on to thrive with the Mets, Dodgers, and Blue Jays, with rumors that multiple teams are interested in dealing for him. Be it as a veteran locker room leader, or a valuable bargaining chip, Granderson could easily have proven to be a key figure for the Yankees had they held onto him.

11 Kept For Too Long: Joba Chamberlain

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Joba Chamberlain was a successful relief pitcher, and popular with the New York faithful. As such it seemed like a sensible enough gamble to promote him to a starting pitcher role. However, Chamberlain faltered in that spot, then struggled upon returning to his relief role, in a downward spiral of value to the team.

In retrospect, the team probably should have kept Chamberlain as a reliever for a couple more years and then parted ways.

Unfortunately, much of his good will was squandered in his ongoing struggles and the Yankees not knowing when to call it on his tenure.

10 Gave Up Too Soon: Aroldis Chapman

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Aroldis Chapman is one of the top relief pitchers in the game. When the Yankees first brought him in as a closer, his talent was largely overshadowed by personal issues as domestic violence allegations haunted him. He wound up being traded to the Chicago Cubs just two months after he’d started playing with New York.

As if it demonstrate that this was a mistake, the Yankees re-signed Chapman going into the 2017 season to a lucrative deal—reportedly the biggest a relief pitcher has earned to date. Now Yankees will get a more comprehensive look at what Chapman can mean to the franchise.

9 Kept For Too Long: Roger Clemens

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There’s no question that Roger Clemens is a legend from the pitching mound. The Rocket became a superstar playing for the Boston Red Sox, only to further his legacy in five season tenure with the Yankees. While his abilities began to trail off, he nonetheless remained an imposing figure and seemed to call it quits at the right time.

Clemens would return, though, first to play for the Astros, and then to come back to Yankee Stadium. By that final season, he was a shell of his former self who had no business starting for the most decorated team in baseball.

8 Gave Up Too Soon: Vernon Wells

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Vernon Wells was a talented player who proved, if nothing else, his flexibility and versatility while playing out the final season of his career with the New York Yankees. He changed his number twice to accommodate legends who’d had their jerseys retired and incoming talent, and played third base and first base for the first time in his 15 year career to give the Yankees what they needed.

In the end the Yankees released Wells ahead of the 2014 season, but he was still paid out his big money contract.

While he may not have been a star, he was a proven veteran role player who may have still contributed, particularly if he was going to have to be paid anyway.

7 Kept For Too Long: Carl Pavano

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Despite expectations that Carl Pavano would be a new star pitcher for the New York Yankees, and the big money contract that came with that forecast, things never really panned out for him in New York. Pavano’s play didn’t exactly make fans’ dreams come true. Worse yet, he got bogged down in oddball situation with a car accident that many outlets reported he failed to disclose to his team.

In the end, the Pavano experiment wrapped up after two seasons but probably should have been called off even sooner.

6 Gave Up Too Soon: Melky Cabrera

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Melky Cabrera had the good fortune of starting his career with the Yankees and even picking up a World Series ring before his tenure there was through. Management gave up on him after five seasons of just OK production, though, thinking that they were cutting their losses on a guy who never made good on his potential. Little could they have foreseen that just three years later he’d not only be an All Star, but the All Star Game Most Valuable Player.

Yes, Cabrera came into his own in the years to follow his Yankees residency. Though allegations of using performance enhancing drugs have more recently put a damper on his success story, there’s nonetheless reason to believe the Yankees should have kept him on the payroll a bit longer.

5 Kept For Too Long: Kei Igawa

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In the mid-2000s, the Yankees took a gamble on bringing in an ace from Japan to freshen up their pitching rotation, and perhaps guide them into a new era. Kei Igawa got a big money deal and a lot of buzz on his way into Major League Baseball, but never did make a successful transition to playing in the States.

Igawa wound up starting just 16 games over two seasons before being shuffled down to the minors and eventually let go.

In retrospect, the team probably would have been better served not to have brought him in, or to have cut off the experiment in his first underwhelming year.

4 Gave Up Too Soon: Robinson Cano

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For every great player, there comes a time when his play will decline, and it’s best for the team he belongs to to start looking toward the future and lessening his role, if not sending him elsewhere. This seemed to be the case for Robinson Cano as the second basemen got on into his mid thirties and, at least in theory, the twilight of his career. The Yankees offered him a shorter, lower money offer to finish out his career with them; Cano took his talents, instead, to Seattle for a ten year deal reportedly worth $240 million.

Thus far, The Mariners have looked wiser than the Yankees on this one, a Cano has continued to produce at an All Star level for at least his first four years with them.

3 Kept For Too Long: Gene Michael

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Looking back, it can be easy enough for fans to conflate longevity with greatness. Gene Michael’s tenure with the Yankees lasted eight seasons, and yet for that stretch he never really proved himself. The guy was never much of a consistent force at the plate. Worse yet, as fielder he once led the American League in errors, and didn’t exactly have a sterling record otherwise. As noted by Fox Sports, perhaps his greatest claim to fame was pulling off the Hidden Ball Trick on multiple occasions.

Michael went on to a career in management with the Yankees, and even in that role didn’t exactly elevate the franchise.

2 Gave Up Too Soon: Ivan Nova

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Ivan Nova emerged as fine pitcher for the New York Yankees, enjoying six and a half productive seasons from the mound before the team traded him to Pittsburgh.

Nova may not have been a star, and wasn’t entirely consistent, but he was more often than not a positive contributor for the Yankees franchise.

He probably deserved better than to be shipped off at the first sign of struggles with his game in 2016. Sure enough, he has continued to a fine career with the Pirates since.

1 Kept For Too Long: Hideki Irabu

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The late Hideki Irabu was a pitching great from Japan who, after one good season of MLB ball playing in San Diego crossed the country to play for the Yankees. After a strong start, the general consensus is that pitchers figured out how Irabu pitched, and Irabu struggled to adjust. So it was that he went from an ace to a more run of mill pitcher.

Irabu’s first season with the Yankee was, on the whole, successful enough, and a fair enough experiment. Keeping him around for two more years with diminishing returns, though, wasn’t the best use of resources for the time.

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