Large contracts in the modern era

Go look at the list of MLB free agents this offseason, then come back. How’d it look beyond Josh Hamilton and Zack Greinke? And even those two players come with flaws.

Hamilton has a well documented history of drug addiction and alcoholism, and any team that signs him has to worry about him relapsing. He also ends up on the disabled list at least once a year.

As for Greinke, he has social anxiety disorder, which may or may not be a concern to some teams. Greinke wished to join the Yankees for the 2011 season, but GM Brian Cashman decided against it because of doubts that the young righty could handle pitching for a big market team.

However, some team will give both of these players way more than they’re worth, because after them the pickens are slim. It happens every year. I expect both of them to get at least seven years and over $120 million.

The number of bad contracts in baseball is astounding. The minimum salary in MLB this year was $480 thousand. For a comparison, in Hank Greenberg’s final season in 1947, the Pirates signed him to a one-year contract that made him the first player to make $80 thousand. Today that equates to just over $800 thousand. That means that the minimum contract in baseball last year equates to more than half of what Greenberg made in the final year of his Hall of Fame career.

It seems like every time a team signs a free agent to a gigantic contract, it ends up badly. Let’s take a look at the top five free agent contracts in MLB history, and you’ll see what I mean.

5. Derek Jeter: New York Yankees (2001-2010) $189 million

This is the one contract that actually worked out. From 2001 to 2010, Jeter hit .310/380/.455 and played “Gold Glove” defense at shortstop (actually terrible, but yay meaningless awards). After hitting .316 in 2012 at age 38, the question is at what point will Jeter not be worth $18 million a year?

4. Prince Fielder: Detroit Tigers (2012-2020) $214 million

The question about this contract was never the first few years, but the middle to end of it. Fielder had a great 2012 offensively, hitting .313/.412/.528 with 30 home runs.

However, looking at past players with Fielder’s body type, it would not be surprising if in two or three years Fielder’s production falls off a cliff.

The jury is still out on this deal, but I think Tigers fans will be celebrating when it expires in 2020.

3. Joey Votto: Cincinnati Reds (2014-2023) $225 million

The Reds signed the 2009 MVP to a 10-year extension prior to the 2012 season. The extension doesn’t start until 2014, making Votto a Red until 2023.

Votto missed about a month and a half with an injured left knee that was operated on twice. Upon his return to the lineup in early September, Votto recorded zero home runs the rest of the season.

Maybe an offseason of rest will do the trick and Votto will come back as strong as ever, but two knee surgeries before the contract even begins is not what Cincinnati was hoping for.

2. Albert Pujols: Los Angeles Angels (2012-2021) $240 million

2012 was considered a down year for Pujols, and he still hit 30 home runs with a .285 batting average as he adjusted to a new league. Many criticized the contract last offseason because Pujols will be 41 by the time the deal runs out.

Maybe they’re right. Maybe his body will start to break down at some point and the Angels will be stuck with him. But make no mistake, Pujols is not just a great player; he’s a historically great player, and betting against him would be foolish.

Alex Rodriguez: New York Yankees (2008-2017) $275 million

A-Rod has actually signed the two biggest contracts in MLB history, as he signed with the Texas Rangers for $252 million in 2001 before being traded to the Yankees in 2004 and opting out of his contract in 2008. The Yankees resigned him to an even bigger contract. A contract that no other team would have given him.

When you bench a player in the playoffs and he’s the highest paid player in MLB history, you know it’s a bad contract. To add insult to injury, the contract still has five years left on it.

However, for all his criticism as a player who doesn’t play well in the playoffs, he did lead the Yankees to a World Series victory in 2009. So the question is if that alone makes the contract worth it. Does one championship make up for years of subpar play? If so, maybe this was a good signing.


As I said before, some team will sign Greinke and Hamilton to huge deals this winter. Whether the contracts will be worth it depends on your point of view. The saying “flags fly forever” comes to mind.

Maybe Hamilton or Greinke will lead their team to a championship. But is it worth that team being crippled financially for years on end?

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