Sports Contracts with Odd Stipulations

Roy Oswalt wanted a bulldozer, and by gum, he got one. (

Roy Oswalt wanted a bulldozer, and by gum, he got one. (

It’s no secret that most major sports leagues are run like a business. That’s partly why, especially in a relatively dead time of year when most major sports are in the offseason, a good portion of the sports news you’ll read pertains to front office happenings. But the front office isn’t always great at what they do. Sometimes, for instance, a few of their officials will take leave of their senses and hack a major franchise for no good reason. Other times, however, they simply write a bad contract. In fact, bad sports contracts are so common, you’d almost think they were a compulsory part of the industry.

If you’ve read a couple of our other list-based articles in the past, then you probably see where this is going. What we are about to present you is not just a list of a few bad sports contracts, but rather an examination of the four most common habits shared by the contracts in question. Some of these are simply bad business deals by people who probably should have known better. Others, however, are outrageous in a slightly more peculiar fashion.

Overpaying Players Too Far in Advance

There’s A-Rod, lyin’ down on the job. (Andrew Mills/THE STAR-LEDGER via USA TODAY Sports)

There’s A-Rod, lyin’ down on the job. (Andrew Mills/THE STAR-LEDGER via USA TODAY Sports)

One of the greatest things that goes wrong with many sports contracts is simply that the team decides to pay a player exorbitant sums of money, only to be disappointed when they fail to deliver quite the performance that was expected of them. This isn’t technically that odd, although one might argue that it is a tad strange for it to keep happening when so many teams have had the opportunity to learn from one another. It seems like they should, rather than committing to pay players outrageous sums for years at a time.

Players like Michael Vick, for instance. Vick has had two nine-figure contracts during his career, with the most recent one still underway. His six-year, $100 million contract with the Philadelphia Eagles might have seemed like nothing compared to his former contract with the Atlanta Falcons ($130 million), but it seems like a lot more when you consider the problems he developed shortly after the money started coming in. Not only did he start fumbling left and right, but the problem got so bad (eight in five games) that Vick started carrying a football everywhere he went in order to “remind [himself]…to take care of the football.”

But you don’t need a nine-figure sum to make a bad contract. If you’re the New York Islanders, all you need is a goalie like Rick DiPietro and the insane belief that he’ll stay in tip-top shape for an implausible fifteen years. His contract extension, granted in 2006, would have kept him around until 2021 for a total of $67.5 million, paid out in $4.5 million increments each year. Too bad they decided they didn’t want him around in 2013. They bought out his contract, and now they’ll be paying him $1.5 million per year until 2029 to do nothing.

Of course, it goes without saying that these players are usually expected to perform much better at the time their contract is given. Such was certainly the case when the Washington Wizards offered Gilbert Arenas a contract for $111 million over six years. And he still made bank, even after his knee started causing issues and waving a gun around in the locker room caused even worse issues. Back in 2013, Arenas was still one of the highest-paid basketball players in the NBA. The real kicker is that he’s not even in the NBA anymore, but rather playing hoops in China.

All of these sports contracts, however, pale in comparison to that of Alex Rodriguez. A-Rod’s contract in 2007, which Steve Politi of CNN literally called “the worst sports contract ever,” was for $275 million paid out over ten years. That was, unfortunately, before the Yankees knew about the issues with his performance enhancers. In fact, the Yankees are now so sore over the Biogenesis scandal that when A-Rod managed to hit his 660th home run back in May, they openly stated that they had no intention of paying out the $6 million bonus it should have earned him. Which, interestingly enough, is not technically a violation of his contract at all. Although it’s not like the Yankees don’t likely have the money.

Paying People Not to Be Involved

While some sports contracts might err on the side of favoritism, asking players to remain with the team long before their skills have been proven, there are some which do the exact opposite. There are some sports contracts which attempt to placate players or owners by offering them extraordinary benefits for their non-involvement with the team. The following are just four examples of such sports contracts. And while there are more sports contracts than this which fit the bill, these are by far some of the most extreme examples of this particular trend.

It was reported earlier this year that Bobby Bonilla would be paid well over $1 million by the New York Mets for his services. So, what’s the problem? Just the little fact that the Mets haven’t taken advantage of his services since the late 1990s. Nonetheless, it turns out he was supposed to earn a few million back in 2000, and New York thought it would be a better idea to pay him out a sum total of $1,193,248.20 every year for a quarter of a century. And if that sounds ridiculous, it’s only because it is.

But Bonilla’s contract looks like nothing compared to that of Shelly Sterling. She sold the Los Angeles Clippers for $2 billion back in 2014, but she didn’t do it for the money alone. She was also given the titles of “Owner Emeritus” and “Clippers Number One Fan.” She was also given one dozen tickets to each of the team’s games, not to mention multiple rings if the team manages to win a championship. She only won the team because her husband made a few insensitive racial remarks, but it still seems like she got a pretty sweet deal out of it.

If you’ve ever heard of Dan and Ozzie Silna, then congratulations on studying your NBA history. Back in 1976, when the NBA joined with the now-extinct ABA, they were the owners of the Spirits of St. Louis. And they wanted one thing if they were going to dissolve their contract. They wanted one-seventh of any television profits made by four ABA teams (the Brooklyn Nets, the Denver Nuggets, the San Antonio Spurs and the Indiana Pacers) which were absorbed into the NBA. The crazy part of the deal was that no one really knew how much it was worth. But by last year, it was worth $500 million. And the Silna brothers were offered an additional payoff in the same amount if they were willing to finally let go of their extreme contract.

The most interesting of all the sports contracts on this portion of the list comes from the USFL. Have you ever heard of them? Of course you haven’t. But they still exist, if for no other reason than to pay former 49ers QB Steve Young. Back when Young signed his five-year, $40 million contract, such numbers were unprecedented. Some people blame Donald Trump for it, but their logic is far less than perfect. In any case, back in 1985 before the USFL folded, Young was considered the highest-paid player in the game. No one knew at the time that his league was about to go under.

Crazy Bans and Weird Restrictions

Curt Schilling was really more incentivized to keep his weight down than banned from gaining any. He eventually quit baseball and became a gamer. (Mark Boster/Los Angeles Times)

Curt Schilling was really more incentivized to keep his weight down than banned from gaining any. He eventually quit baseball and became a gamer. (Mark Boster/Los Angeles Times)

While some players and sports owners are given sports contracts which essentially pay them to stay away from the team, others are quite welcome. Unfortunately, however, some of these players are not necessarily accepted as they are. As such, some sports contracts ban players from engaging in actions which do not seem preferable for one reason or another. Other times, they simply offer them bonuses to keep them from engaging in non-preferred actions. Sometimes, the motivations for these types of sports contracts seem relatively clear. Other times? Not so much.

A few years after the start of the new millennium, Curt Schilling of the Boston Red Sox found himself receiving an interesting offer. The contract itself was fairly run-of-the-mill. It was for one year, valued at $8 million. What made it interesting, however, was the stipulation that he would be weighed half a dozen times during the season without receiving prior notice. These random weigh-ins were worth $333,333 each, but only if he was able to keep his weight down. In other words, he could collect close to an extra $2 million on his contract, but he was restricted from gaining weight if he wanted to do so.

You might not have heard of Stefan Schwarz before, at least not from us. We normally don’t spend too much time on soccer since it isn’t included as a part of our handicapping consulting services, but Schwarz fits onto this particular list pretty well. Why? Well, because he might be the only soccer player to be banned from space travel. This is certainly not a common provision in most sports contracts, but the issue was established back when one of Schwarz’s advisers was expected to take part on a commercial space flight in 2002. Schwarz’s team wasn’t sure they’d be able to insure him for such an occasion, so they simply banned him from partaking at all.

If you’ve heard of Rollie Fingers, it’s probably either because of his skills as a baseball player or because of his mustache. Fingers has a handlebar mustache that would make Snidely Whiplash jealous, but it wasn’t just a personal choice. He grew out his mustache back in 1972, after Charlie Finley, owner of the Oakland A’s, offered $300 to any player willing to do so. But, baseball players are often superstitious. And the same year Fingers grew out his mustache, his team won the World Series. So he kept it. And they won again. And again. Because sometimes, it isn’t sports contracts that truly bind the players with crazy restrictions. It’s the players themselves.

We talked about A-Rod’s contract earlier, but here’s an interesting fact that we didn’t cover: he can’t buy game tickets. Or, to be more precise, he can only buy game tickets. A lot of baseball players get them for free, but one of the premier members of the Yankees is not among them. The best he can do is to buy four suites for the games. Now, the ability to purchase these suites at a discounted rate is certainly nothing to sneeze at. But it’s still a little strange that he can’t just get a few stadium tickets for free, given how commonly this privilege is included in players’ contracts.

Baffling Perks and Forms of Payment

He’s a pretty big fan of that number. (The Richest)

He’s a pretty big fan of that number. (The Richest)

Now, this is the sort of thing we’re really here to talk about. The truly strange offerings that sports contracts sometimes give their players. Technically, we’ve already mentioned this a few times. As we said, Fingers wasn’t technically banned from shaving his mustache, but rather paid to grow it out and felt as if he couldn’t shave it when the team kept winning. And we also talked about Shelly Sterling, with her strange titles and possibilities of winning multiple championship rings. (Seriously, who needs more than one?) But these last four sports contracts were among the most interesting we could find.

In 2005, a verbal contract was made with Roy Oswalt of the Houston Astros. He was told that he would get a bulldozer if he could help the team to clinch an appearance in the World Series. And sure enough, that’s what he was given: a Caterpillar D6N XL, to be precise. Despite his appearance in the World Series, Oswalt said that the bulldozer was what would be the envy of his friends and neighbors. And it went to good use, too. In 2009, Oswalt decided to build a restaurant in his hometown of Weir, Mississippi. He used the bulldozer to clear the land.

College athletics aren’t immune to crazy sports contracts, either. Take, for instance, Mike Leach, coach of the WSU Cougars football team. Not only was he ranked as the most overpaid college football coach just earlier this year, bus his contract also nets him 150 tickets to away games in addition to twenty tickets to home games and a suite with eighteen seats in it. It’s the “150 for away games” that seems especially high. He’s allowed to divvy them up between away games in whatever manner he chooses, so he could technically take them all in one go if he wanted.

We’re going to bring up soccer again, because this one is just too good not to mention. It isn’t technically a payment, but we like to think of it as a free meal. The meal in question was given to player Spencer Prior by Sam Hammam, owner of the Cardiff soccer club. Apparently, Prior was contractually bound to eat sheep testicles. In another show of generosity, Hammam allowed the player to cook his delicacy and serve it “in a lemon and parsley sauce.” Oh, and there was also something about Prior having to engage in a “physical liaison” with the sheep before he ate it. But we’re assuming that part was never enforced.

This article is going to end with a tie between two baseball players, both whom were given exactly what they wanted. First up is Turk Wendell, who joined the New York Mets as number 99 back in 1999, and requested a 99-cent bonus on top of his $1.2 million contract. He wasn’t greedy. He just really wanted his salary to end in 99. And then our other first placer on this list of odd sports contracts is Charlie Kerfeld who, much like Wendell, was passionate about his uniform number. Renegotiating his contract with the Houston Astros in the mid-1980s, he asked for his number (37) to be incorporated into his $110,037.37 contract. He also asked for 37 boxes of Jell-O, which we’re sincerely hoping went to good use.