MLB's 10 Most Ridiculous Contract Stipulations

The MLB free agency period paves the way for heated, stressful and tedious negotiations between two sides fighting for every penny.

Some bizarre contract stipulations will make you wonder if this process robbed them of their sanity.

Contract clauses are eminent in a majority of modern deals, usually for good reasons. Wherever Josh Hamilton signs this offseason, he will probably receive a bonus for winning the MVP, capturing a Silver Slugger honor and/or earning All-Star appearances.

But what happens when a designated hitter is offered extra money for snatching a Gold Glove and a subpar relief pitcher gets challenged to start the All-Star Game?

A couple of these agreements show just how much power big-name players hold in negotiations now, but many of these weird contract clauses were likely consummated in good fun. As long as neither side actually believes it can happen, no harm is done.

So, largely with the help of ESPN's Jayson Stark and Ethan Trex at CNN, let’s get a good laugh from some of the odder contract clauses agreed upon in the MLB.

10. Albert Pujols Is Set for a Long Time

When Albert Pujols signed a mega-deal with the Los Angeles Angels of Anaheim, he netted himself 20 years of employment.

Ten years and $240 million apparently was not sufficient in convincing Pujols to abandon St. Louis after locking down his second World Series title, so the team also included a 10-year, $10 million personal service contract to keep the star as a member of the organization following retirement.

In what other profession can someone land an agreement with two 10-year jobs?

Now this is the furthest thing from ridiculous for Pujols, who took advantage of his leverage as one of this generation’s top players. And while retiring early as a millionaire seems outstanding, not being able to cash in on your primary skill set at age 40 could become a scary endeavor.

As for the Angels, this contract could get really ugly really soon. Although hitting .285/.343./516 with 30 homers and 105 RBI is great for a mortal, it’s not “I’m so glad we have him for nine more years at $228 million” great.

Pujols’ savvy deal could certainly set a precedent for future superstars worried about life after their playing career.

9. Rollie Fingers Paid Not to Shave

Rollie Fingers lived every month like it was Movember.

While some teams today enforce strict rules limiting unruly facial hair and killing the legend of the caveman, Oakland Athletics owner Charles Finley encouraged Rollie Fingers to grow his now-famous handlebar mustache.

According to Trex, Finley offered all his players a $300 bonus if they grew a mustache before Father’s Day during the 1972 season. Fingers, who won an American MVP and Cy Young award over the course of his 18-year career, obliged and turned the railroad-track-villain look into his signature.

Coming from someone who has failed miserably to grow any semblance of a beard that makes him appear older than 14, Fingers deserves major props for his fine ‘stache.

Even Ron Swanson would approve.   

8. Carlos Beltran Eyes New Hitting Equipment

Before Carlos Beltran could cash in on an extraordinary 2004 postseason with the Houston Astros and flood New York Mets fans’ heads with undelivered promises of a fresh start, the star center fielder needed some new equipment installed in Queens.

In addition to receiving $119 million to become the face of the “New Mets,” Beltran’s contract required the Mets to lease Conditioned Ocular Enhancement equipment, also known as a machine that spits out tennis balls really fast.

The machine will deliver balls to batters at increasing velocity, eventually hitting 150 miles per hour. This device works to enhance a batter’s eye and quicken his reaction time at the plate.

One question remains: When the Mets traded Beltran to the San Francisco Giants in 2011, who kept the machine? The Mets probably need it a lot more right now.

7. Which Pittsburgh Pirate Will Win World Series MVP?

The Pittsburgh Pirates still have quite a way to go before competing with the league’s top clubs, but they are no longer the sport’s easiest punch line. Baby steps...

Optimistic that better days awaited, Pittsburgh offered six players bonuses for winning the World Series MVP award. And no, we’re not talking about Andrew McCutchen. Kevin Correia was the best of the bunch, but to be fair, this is an award previously won by David Eckstein.

This one actually makes some sense. The players have a small reason not to give up in early August while the Pirates can dream of a scenario that is at least mathematically plausible.

None of the players are still under contract, so maybe the Pirates will hold off on distributing World Series MVP clauses like candy on Halloween after coming close to a .500 season.

6. Charlie Kerfeld's Massive Jell-O Haul

Astros’ pitcher Charlie Kerfeld did not treat the negotiation process with much gravitas.

A couple facets of Kerfeld’s contract make it especially unique. For starters, he looked at teammate's Jim Deshaies recently signed $110,000 deal and decided he wanted to out-earn his follow pitching colleague. So Kerfeld settled for $110,037.37.

Further extending his love for 37, his number at the time, Kerfeld requested, nay, demanded 37 boxes of orange Jell-O. He drove a hard bargain, but the Astros caved.

They really shouldn’t have though. Kerfeld registered a 6.67 ERA the year after receiving his new contact.

I would have held out for some M&M’s, but that’s just me. He signed the deal in 1987, so the extra $0.37 he finagled could have probably scored him some candy.

5. Oh Man, Will Ohman Is Starting the All-Star Game

If you thought R.A. Dickey starting the 2012 All-Star Game would have cemented an unlikely story…

When etching out a contract with relief pitcher Will Ohman, who posted a 1.50 WHIP the previous season, the Chicago White Sox addressed the elephant in the room: How will they reward the stud’s inevitable All-Star bid?

Ohman, according to Stark, was one of three middle relievers who received a bonus clause in their contract for starting the All-Star Game.

Shockingly, Ohman failed to even make the All-Star roster, posting a 4.22 ERA and 1.31 WHIP in 2011.

After allowing 19 runs in 26.1 innings last season, Ohman is still sitting on free agency, waiting for someone to offer him an incentive to win the Cy Young.

4. Roy Oswalt Bulldozes the Competition

When Roy Oswalt won Game 6 of the 2005 National League Championship Series, he earned way more than a chance for the Astros to win a championship.

Sure, sealing a trip to the World Series is cool and all, but Oswalt had a much bigger reward in his sight. Before the game, team owner Drayton McLane motivated his ace by pledging to buy Oswalt a bulldozer if he secured the victory.

With the sweet allure of a bulldozer guiding him to greatness, Oswalt pitched seven superb innings, allowing three hits, one walk and one run while striking out six batters. A man of his word, McLane officially added a bulldozer clause to Oswalt’s contract and purchased the wrecking machine.

The world would be a far more productive place if everyone was bribed with a bulldozer.

3. Meet Baseball's Top Slugger: Chien-Ming Wang

Chien-Ming Wang and the Washington Nationals both knew that the mediocre, injury-plagued pitcher was not about to win any awards for his pitching.

But maybe his bat could bring home some hardware.

Wang, who previously played in the American League for the New York Yankees, expertly seized a $50,000 clause for winning the Silver Slugger award. He had yet to tally a hit in five prior seasons, but everyone knew he was due. After spraining his foot during one of his rare baserunning opportunities, Wang was eager to return to the majors and prove his merit as the next Babe Ruth.

Adding such a stipulation was probably a waste of time for Washington, but then again, so was signing Wang in the first place.

2. Can Adam Dunn Win a Gold Glove as Best Defensive DH?

Seriously, whoever penned the White Sox’s contracts in 2011 sure has a sense of humor.

After entertaining the option of Ohman highlighting the Midsummer Classic, it was time to negotiate with the best defensive player of this generation: Adam Dunn.

Chicago inked the slugger to a four-year, $56 million deal in 2011, but they needed to sweeten the pot just a bit more.

What incentives do you provide a man who almost annually (with exclusion to an abysmal 2011) approaches 40 home runs? Maybe a bonus for notching 500 career home runs? A little something extra for netting a Silver Slugger?

Nah, how about $25,000 for winning a Gold Glove?

Not only would that mark Dunn’s first Gold Glove, but it would also make Dunn the first player to win the award from the comfort of the dugout while serving as the designated hitter.

Maybe Dunn stumbled at the plate in his first year in Chicago because of the intense pressure of saving runs from the bench.

1. Why Can't Manny Be Someone Else?

While most of the other odd stipulations are harmless, Manny Ramirez’ past contract with the Boston Red Sox represents the mindset of a seven-year-old.

A no-trade clause is a reasonable request for a star of Ramirez’ stature, but he did not ask for one. Unless another Red Sox got one.

That’s right, Ramirez actually instituted a stipulation that enacted a no-trade clause if a teammate later agreed to a deal with one in place. He didn’t want one enough to just ask for it, but he’d be damned if somebody else received an amenity not offered to the great Manny Ramirez.

So here’s how this negotiation probably transpired:

Ramirez: I don’t need a no-trade clause. I want to end my career in Boston.

Red Sox: Okay, great. We were just checking because some other stars usually ask for one their contract.

Ramirez: Wait, someone else can get something that I don’t have? That’s not fair!

Red Sox: Fine, but how old are you?

Ramirez: It’s just Manny being Manny. That makes my self-centered, juvenile behavior okay.