MLB: New York Yankees at Toronto Blue Jays

We live in dizzying times. Baseball player salaries continue to climb higher as more and more money enters the game. The Players Association and owners collectively bargained to ensure the players – the active players – get a bigger piece of the pie just two years and already we see the aftereffects.

Freddie Freeman, a good if unspectacular first baseman for the Atlanta Braves, just signed a contract worth more than $130 million. Eight years is a long time and Braves fans hope his name doesn’t end up on a future version of the worst contracts list.

The same holds true for fans of Albert Pujols, Prince Fielder, Clayton Kershaw, and Joey Votto, all with more than $200 million coming their way. Will they end up among the worst contracts in baseball history? If so, they join the same names you see below.

8. Bill Caudill – 4 years, $7 million

Bill Caudill doesn’t have the big name or the big bucks of some of the other entrants on this list. But his contract came during the nascent days of free agent spending, especially for relief pitchers. Heading into is final year of arbitration, the Toronto Blue Jays acquired Caudill from Oakland in a trade and then inked a five-year deal worth $7MM – in 1985.

That’s a big payday for a relief pitcher, especially won with two very good seasons and two somewhat suspect seasons on his resume. His first year in Toronto, Caudill pitched well in helping the Jays claim their first playoff berth and AL East crown. Then he was bad and then hurt and back in Oakland and then out of baseball.

The architect of this deal? A 33-year old hotshot by the name of Scott Boras. Boras’ strong-arm tactics, not to mention hiring a plane to fly a message over the field, goading Toronto manager Jimy Williams into using the middling reliever. It set relations between Boras and the Canadian club back quite a distance, a relationship that never quite recovered.

7. Barry Zito – 7 years, $126 million

San Francisco Giants v St Louis Cardinals - Game Five

Barry Zito’s contract stands out because the San Francisco Giants paid for a superstar and got barely a fifth starter for their trouble. His arm stayed attached and only missed time in 2011 because of a foot injury but he was also sort of never good. He certainly could not have survived outside the friendly confines of AT&T Park.

But he did survive. He made 200 less than spectacular appearances for the Giants and pitched more than 1100 innings. He also, by the way, won two World Series rings and did, in fact, make some terrific playoff starts against all odds.

It is hard to call a contract one of the worst all-time when it results in this kind of sendoff. Ill-advised? Maybe. Worst. Hardly.

6. Carl Pavano – 4 years, $39.95 million


This is the opposite of the Barry Zito contract. Carl Pavano was always hurt and it drove Yankees fans BANANAS. They booed him off the field when he left a game injured in 2008 because, well, that happened often.

Pavano made a mere 26 starts for the Yankees over the life of his deal, missing all of 2006. It was short but it still counts as one of the worst ever.

5. Bobby Bonilla – 5 year, $29 million


Bonilla’s contract with the New York Mets is less bad than famous. It was the largest in the game when he signed it but he fell somewhat short of earning the total value in Flushing.

But it became the stuff of legends as he agreed to a deferred buyout (or two), receiving payments for 25 years rather than $5.9 million upfront in 1995 but more than $25 million spread out over 25 years, beginning in 2011.

As usual with infamous contracts, it is superstar money given to players who don’t produce at superstar levels. But with the kind of retirement deal Bonilla scored from the Mets, it deserves its own place on this list.

4. Kevin Brown – 7 years, $105 million


Somebody had to be baseball’s first $100 million man and it was Kevin Brown. It wasn’t out of line, considering just how dominant Kevin Brown was for his career up to this point. Some might call it a Hall of Fame career.

But Brown moved around and spent too much time on too many teams then inked this deal and it seems to be the only thing people remember him for, not the years and years and years of excellent pitching.

The Los Angeles Dodgers signed Brown to this deal when he was 34-years old, warning sign number one. Brown was outstanding for the first two years of the deal. He pitched 480 innings and posted more than 13 Wins Above Replacement. But at age 36 he only made 19 starts and the following year he was slowed again by injury.

Brown finished his career, and this deal, with the Yankees but it feels like this deal looms over him in retirement. Again, more misguided than bad, a seven-year contract for a pitcher in his mid-thirties was doomed from the start.

3. Jason Schmidt – 3 years, $47 million

Los Angeles Dodgers pitcher Jason Schimidt throws to first base in a baseball pitching drill during spring training camp in Glendale

Or maybe all contracts for 34-year old pitchers are bad? Perhaps that’s only if the Dodgers sign them. Schmidt signed a huge deal with the Giants when he first became eligible for free agency and it worked out just fine. But the three year contract he agreed to with the Dodgers ahead of the 2007 season was bad from the start.

Despite looking like a “steal” according to young ESPN analyst Keith Law, Schmidt could only make 10 starts total for LA. Another pitcher overshadowed by a big contract that went bad, this was a mess from the beginning.

2. Mike Hampton – 8 Years, $121 million


This is essentially the gold standard for bad contracts. The eight years included two different Tommy Johns and a grand total of 147 starts, made with a sterling ERA+ of 98…for two different teams. The team that signed the deal only ended up on the hook for two years of the deal.

It was the largest deal in sports at the time, signed by a team desperate to figure out their pitching problems – problems that persist even today. Hampton was a 4 WAR pitcher leading up to his signing in Colorado but only produced 2.9 Wins Above Replacement for the entire life of this deal.

That’s a bad contract. One of the worst, really.

1. Alex Rodriguez – 10 years, $275 million

Puns are not for the weak, Alex

The first ridiculous deal Alex Rodriguez signed, with Texas in 2001, was fine. It was insane but Alex Rodriguez was literally and figuritively an insane baseball player. Pariah as he might be, he produced as well as could be humanely expected, even if it required some non-human measures to accomplish.

A-Rod’s deal with the Rangers included an opt out after the 2007 season, an option the 31-year old took with pleasure. The Yankees agreed to another ten year contract with Rodriguez, this one stretching until 2017 when the former shortstop would be 41.

The deal included endorsement bonuses for milestone home runs and all manner of controversy emerged from the aftermath, of course. There was a chance Alex Rodriguez, of all people, could earn his worth in such an unusual contract. But it didn’t happen that way. And now it’s the biggest mess in the sport. A mess the Yankees would love to extracate themselves from but, for now, they’re stuck. Stuck with Alex Rodriguez for three more years after he returns from his season-long suspension.

Oh, what a mess indeed.