The Top 5 Worst Signings in MLB History


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In baseball money talks, and sometimes the money talks more than the players walk. When this happens we see players with contracts that make us shake our heads. Here are the 5 worst signings in MLB history.

Although technically I was including the entirety of baseball history for this list, I chose to stick fully with contracts signed in the last decade or so. The reason for this is because player salaries have increased so much in the last 20 years or so that bad contracts hit the books a lot harder now than they did in earlier times. I understand that owners also did not make as much money then and that even though the contract was lower it might have hit the books similarly badly.

That being said, it’s still my opinion that the contracts today are such an enormous amount higher that they are worse.

This list is mainly based on the amount a player made per year compared their performance, or lack thereof. As there have been a multitude of horrendous free agent signings it was sometimes hard to differentiate which signings were the crème of the crop (or shittiest of the litter).

But after long hours of toiling over player numbers and contracts, I have finally come up with a list of the worst free agent signings in baseball, and here it is.

Best Worst of the Rest

Not bad enough but deserves a shout out

Gary Matthews Jr. – OF – 5 years/$50 million – Los Angeles Angels 2007

A $50 million contract for a 32-year-old journeyman coming off a career year at hitter friendly Rangers Ballpark… never a good idea. Predictably, Matthews production began to heavily digress as he batted just .248/.325/.383 and provided substandard defense in 3 years with the Angels who consequently picked up most of his salary to move him to the Mets. Matthews Jr. made 38 appearances in New York and hasn’t played in the big leagues since.

Jason Giambi – 1B/DH – 7 years/$120 million – New York Yankees 2002

Initially, Jason Giambi seemed poised to live up to his lofty contract as he hit 82 home runs, and had 229 RBI in his first two seasons with the Yankees. Unfortunately, in his 3rd season, Giambi’s game began to go to pieces as he only played in 80 games, batting only .208 with 12 home runs. Giambi was also implicated for steroid use in 2006 and in the last 5 years of his deal made over $240 thousand per RBI (382).

Carl Pavano – P – 4 years/$39.95 million – New York Yankees 2005

Although this is one of the smaller contracts on the list, the ineptitude of Pavano’s tenure in New York certainly earns him a mention. After an 18-8 record, and 3.00 ERA in his last year with the Marlins, Pavano managed only 145.2 innings in three years with New York. Making matters worse the pitcher posted a 4.86 ERA and only 9 wins as a Yankee.

Contracts to Watch

Zack Greinke – 6 years/$147 million – Los Angeles Dodgers 2013

Greinke has been an above average pitcher for most of his career but he has not proven worthy of the $147 million that the Dodgers paid him during the 2012-13 offseason.

Already 29, Greinke is on the back side of his prime and will most likely see his abilities diminish as the $24.5 million per year deal plays out. Look for this deal to look worse and worse as each year goes by.

Albert Pujols – 10 years/$240 million – Los Angeles Angels 2012

10 year deals for players over 30 years old, simply put, are bad deals (see: Alex Rodriguez), but thats what the Angels decided to offer Albert Pujols in exchange for his services.

In year one of the deal “The Machine” promptly posted career lows in batting average (.285), on base percentage (.343), slugging percentage (.516), home runs (30) and fWAR (3.9).

Not the most promising season for someone receiving $24 million a year for the next nine seasons. Did I mention he will be 41 when the deal ends…

Just Missed The Cut

Barry Zito has had ups and downs, but mostly downs in San Fran.

Barry Zito has had ups and downs, but mostly downs in San Fran.

Bad enough for The Bottom Five but an extenuating circumstance kept them off.

Barry Zito – P – 7 years/$126 million – San Francisco Giants 2007

At the time it was the biggest contract ever given to a pitcher and almost immediately, the deal was a bust. In his six seasons in San Francisco, Zito has never posted an ERA under 4.00 and his record has finished below .500 in every season but one. Although Zito has miserably failed to remotely live up to his salary, he saved himself from the bottom five because he has at least been a durable rotation option (he started at least 30 games in every season but one).

Zito also had a very strong 2012 postseason (2-0 with a 1.84 ERA) as he helped the Giants win the World Series.

Juan Pierre/Andruw Jones – CF – 5 yrs/$44 M (Pierre) 2 yrs/$36.2 M (Jones) – LA Dodgers ’06/07

After years of tried and failed experiments, mostly by the Yankees, it was the Dodgers who finally unearthed the answer to the age-old question: how can we make a bad signing worse?

The solution: make a bad signing, wait one year, make 2nd bad signing that MUST: 1. Play the same position as your first bad signing, 2. the second signing must proved the worse of the two deals, and 3. you discover that the best option for that position is a player you have had all along.

After a relatively unproductive first season for Juan Pierre the Dodgers did just that by signing the aging free agent Andruw Jones, fresh off his worst season as a pro, to a two-year deal worth $18.1 million a year.

Jones proved that his bad season was not a fluke by batting only .158 with 3 home runs in 2008 before moving to Texas the following year as the team discovered that their best CF had been with the club all along: Matt Kemp.

Chan Ho Park – P – 5 years/$65 million – Texas Rangers 2002

After a decent 2001 campaign (15-11 3.77 ERA…eh) Texas made the quizzical move of signing Chan Ho Park to, then, one of the most lucrative deals ever given to a pitcher.

Park failed to live up to his lofty expectations as he went just 10-11 with an ERA well over 6 in his first two seasons with the club. Park’s career was then hampered with injuries and he left Texas never having achieved an ERA under an abysmal 5.74 in a season. Park avoided the Bottom Five because on this list, a 5 year deal seems short compared to most of the others.

Five years gave the Rangers at least some leverage and they were able to unload Park to San Diego in the middle of his 4th season. If he had been signed for 7 or 8 years Texas would probably not have been able to get rid of him for several more years.

Daisuke Matsuzaka – P – 6 years/$52 million + $51,111,111.11 bid for rights – Boston Red Sox 2006

Remember the insane intrigue surrounding this starlet Japanese pitcher who we were told could throw 7 different pitches including the mythical gyro ball? A pitcher so coveted that the Red Sox willingly paid over $51 million to his Japanese club to be allowed just to negotiate with him?

You know, that guy they signed to a very lucrative $52 million contract (with incentives that could raise it to $60 million) that would make sure they retained his services for the next 6 years? Yeah, that was Daisuke Matsusaka and that… decision… was a huge mistake.

In truth, Daisuke showed promise early and for most of his tenure with the Sox was largely un-hittable. Unfortunately, just as much as hitters couldn’t hit Daisuke, Daisuke  couldn’t actually hit the strike-zone and as long he was throwing ball after ball, that talking point became moot.

There were some highs but far more lows in Matsusaka’s career in Boston and when his contract finally expired the Sox had paid over $100 million for six years of absolute inadequacy. With a 4.52 career ERA that had digressed substantially from his early years and force Daisuke to be included as one of the worst free agent deals in baseball history.

The Worst Five

The worst of the absolute worst.

5. Alfonso Soriano – LF – 8 years/$136 million – Chicago Cubs 2007

Alfonso Soriano is unparalleled in this list because when he was right, he actually had the potential to live up to his pricey $17 million per year salary. Unfortunately, when Soriano got to Chicago he was unable to build on his epic 2006 40 home run 40 stolen base season in Washington, instead reverting back to the form he resembled while playing for Texas.

This turned into a strike out... seriously!

This turned into a strike out… seriously!

Although Soriano’s contract is one of the worst in baseball’s history, it’s not to say that he was completely unproductive in Chicago and has managed to total at least 20 home runs in each of his first six seasons.

Time and time again, he will show flashes of brilliance and, for just a moment, you understand exactly why the Cubs signed him.

But every time, just when you think that this is it, that Soriano is finally going to turn the corner and fulfill his potential… he strikes back with a painstakingly frustrating moment of failure.

It’s as if he is almost mocking the Cub’s fans who, after cautiously climbing back on the wagon, are once again thrown violently into the all too familiar hypothetical ditch of despair and are left cursing the Soriano name as they cut their wrists.

The untapped potential of Soriano is probably the most discouraging thing about the player. The skill set he possessed allowed him to do things that very few others could, and made you want to root for him. Soriano’s electric arm, home run swing and breakneck speed have made him one of the most exciting players to watch in professional baseball.

Unfortunately, Soriano either refused to or remained incapable of learning to lay off bad pitches. In his 12 year career Alfonso has been in the top 10 in strikeouts a whopping six times and now sits in 35th on the all time list (currently 8th among active players).

The vastness of Soriano’s ability have made it possible to forgive some of his deficiencies such as his poor on base percentage and his propensity to swing at pitches several feet wide of the plate (in a one run game, with the bases load, two outs, and a 3-2 count) because just as he is likely to fail miserably he is as likely to succeed tremendously.

As Soriano began to reach his mid 30s however, his diminishing speed and defensive range in the outfield have made his weaknesses more and more glaring.

He has averaged 27 home runs, 10 stolen bases, and 79 RBI per season but his .265 batting average and .320 on base percentage are far from ideal numbers for a primarily lead off hitter, especially one who’s paid almost $20 million per season.

4. Alex Rodriguez – 3B – 10 years/$275 million – New York Yankees 2008

$27.5 million dollars a year… for 10 years… to a guy thats already 32 years old; it was the recipe for a disaster. After opting out of the final year of his already grossly enormous contract, the Yankees panicked, bid against themselves, and rewarded the superstar with the most lucrative contract in American sports history.

If the club had shown a bit of patience they most likely could have retained A-Rods services for 3 years and 80 million dollars less that they had signed him for.

If that had happened, A-Rods deal may not have even made the list as the Yankees did win a World Series in which Rodriguez batted .250 with a HR.

Unfortunately, the coming years were riddled with a series of injuries and not one, but two different steroid allegations. As A-Rods production began to steeply declined, his injuries have greatly diminished his chances of breaking the home run record, his steroid use means that even if he does break the home run record people still wont give a shit, and finally; he really is just a massive douche-bag (examples of this are his boring P.C. interviews, his steadfast denials followed by practiced tearful confessions that no ones buying, and lets not forget the infamous feed-me-popcorn Super Bowl fiasco).

Popcorn anyone?

Popcorn anyone?

Currently recovering from a long-term offseason surgery, coming off the worst season of his career (in which he was BENCHED during the postseason), and marred by his second PED allegations, the Yankees still owe Rodriguez over $100 million during the next five years, absurd money for what is now just an average player. His contract is so damning that the Yankees will likely have to pick up most of the money in it if they are to move him to another team.

The worst is that paying a guy possibly $15 or $20 million a year to NOT play for you is almost better than the alternative of him actually playing for you. Because the entirety of the deal has not concluded, A-Rod now sits at 4th on the list of worst contracts, but judging by the consistent decline in his numbers, look for A-Rod to move up the list in the coming seasons and possibly even make a strong run at number 1.

3. Jason Bay – LF – 4 years/$66 million – New York Mets 2010

When the deal was signed, few people would have predicted that Jason Bay’s 4-year $66 million contract would end up on this list.

They avoided a dreaded long-term deal and although $16.5 million a year is steep, it is far from unreasonable for a guy with an OPS of .895 or better in five of his six MLB seasons. But when you open a ball park where it is impossible for a right-handed pull hitter to hit home runs, then immediately pay huge money to a right-handed pull hitter who hits home runs, well, that’s how you end up on this list.

In his 3 seasons with the Mets, Bay has seen his batting average decline from .259 in year one to an abysmal .165 in year three (.234 in his joint 3 seasons), he has hit only 26 total home runs (before he had hit at least 26 home runs in each season but one, in which he hit 21), and has battled injuries and altogether awful play.

Although the length of the contract allows the Mets to avoid a situation similar to the Yankees with A-Rod, Jason Bay pops up 3rd on the list because of his absolutely inept play on the field. Last season, Bay was so incredibly awful that the Mets were actually better off when he was not playing at all.

Luckily (?), Bay was injured for the majority of the season and only managed to take part in 70 of the teams 162 games. Thankfully for the Mets, they only have to pay Bay’s obscene salary for one more season.

It’s due to the contract’s relatively short length that prevents Bay from being higher on the list but the ineptitude of his play during that contract ensures his definite inclusion.

2. Vernon Wells – CF – 7 years/$126 million – Toronto Blue Jays 2008

Did you know that in 2012 the highest paid player in Major League Baseball was Alex Rodriguez? Well, yes, you probably did… but, do you know who the second highest paid player in 2012 was? That’s right, it was Vernon Wells… Vernon Wells?!??!!

In truth, Wells wasn’t really even a free agent when he signed his extension with the Blue Jay’s, but the absolute barbarity of his play makes his inclusion on the list a near necessity.

Although Vernon Wells had been a good, or slightly better than good player, for the majority of his career, $126 million for a player who’s on base percentage had never exceeded a .359, had only driven in 100 RBI, hit .300, or had 30 home runs three times, and only stole more than 10 bases twice is already completely outrageous.

Then, when that player’s good, or slightly better than good numbers not only drop, but plummet, that player books a first class ticket to the list of worst free agent signings of all time.

Vernon Wells declined drastically after signing his new deal

His first year after signing the deal would best be described as average. Wells hit .300 with 78 RBI but only participated in 108 games and his WAR was 1.8… ehh… Looking back now however, Well’s 2008 season was an absolute gem compared to what transpired over the next four years.

In that time, Wells has hit .260, .273, .218, and .230 and his on base percentage has slipped below .300, an unfathomable mark for any MLB player.

At 34 and with his BA and Power numbers declining, Wells’ best days are far behind him. But with his biggest pay days still lying ahead, Vernon Wells comes in 2nd place on the worst free agent signings in the history of MLB.

1. Mike Hampton – P – 8 years/$121 million and Denny Neagle – P – 5 years/$51 million – Colorado Rockies 2001

The number one Worst free agent signing in Major League Baseball history has to go to the 2001 Colorado Rockies. The Rockies, stand alone at the peak of dismal signings because they had the misery of signing not one, but two of the worst signings ever and compounded that mistake by signing them… during the same offseason…

Mike Hampton came to the Rockies after a sublime 22-4 2.90 ERA season, and was largely expected to turn the Rockies pitching staff around and worth his $15.25 million per year deal.

Unfortunately, the idea that Hampton didn’t live up to his expectations is a massive understatement compared with how dreadful he actually was as a Rocky.

In his first season Hampton went 14-13 with a 5.12 ERA then regressed further in his second year, going 7-15 with a 6.15 ERA.

After his second atrocious season, Hampton was traded to the Florida Marlins, and then the Atlanta Braves. He showed promise in 2003 of coming back to form but was hit with several injuries that largely derailed the rest of his career.

The gruesome…

… twoseome !








Where Hampton may have been the worst signing in baseball history by himself, the pitcher brought in bolster the rest of the rotation, might have also have been squarely in the top 5.

Denny Neagle was already just a slightly better than average pitcher. He had had a few really good years but they had been mostly earlier in his career.

In the last few years before he signed with the Rockies he had ERAs of 5.81, .3.52, 4.52, and 4.27; not terrible numbers but it was a stretch already to say that he was worth over $10 million per year.

Like Hampton, Neagle was far from coming close to living up to his contract or expectations. In his 3 years for Colorado, Neagle was a joint 19-23 with ERAs of 5.38, 5.26, and 7.90.

Neagle was then sidelined with an injury that kept him out of during his 4th year in Colorado. At the end of the 4th year Neagle retired after 13 years in MLB.

The Rockies gave contracts of $121 million and $51 for the services of two pitchers who pitched for them for a joint 5 seasons. During that time, neither of the players could muster and ERA under 5.00, a number poor for even the worst starting pitchers in the league.

Luckily for the Rockies, they were able to get themselves out from under both of these deals before the expired. That being said, the move for Mike Hampton and Denny Neagle still stands alone as the by far the worst free agent signing… err, signings… in the history of Major League Baseball.

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  • THollister

    Alex Rodriguez wasn’t the MVP of the World Series with the Yankees the year they won. Hideki Matsui was.

    • Stefan Jagot

      Thank you, and you are correct. We will be changing this immediately.

  • Jeff Simons

    You completely missed when the Rangers signed A-Rod, far more of a disaster then the yankees resigning him, it killed the team for almost a decade.

    • @RealPaulBeroza

      He averaged .305, 52 home runs, 132 RBI, an 8.6 WAR, and won an MVP at Texas. Sorry but those numbers just do not put him on the list. He was making relatively the same amount as many other players included and producing at an exponentially higher clip.

      • Jeff Simons

        Numbers are far from the only thing that matter here, he put team chemistry in the shitter when he was here, and ruined the team financially when he left, he was a disaster, no matter how good he played.

    • @RealPaulBeroza

      He also won 3 MVPs and finished 2nd once over the course of the deal. There are few if any teams that wouldnt pay 22 mil per year for a guy that was going to win 3 MVP in 7 years. He was the best player in baseball during that contract.