Are Long-Term Contracts Worth the Risk in Major League Baseball?

We take a look back at every long-term deal signed since 2010, to decide if big free agent contracts are worth it in Major League Baseball.

Manny Machado
SAN FRANCISCO, CALIFORNIA - MAY 22: Manny Machado #13 of the San Diego Padres warms up in the on-deck circle during the game against the San Francisco Giants at Oracle Park on May 22, 2022 in San Francisco, California. (Photo by Lachlan Cunningham/Getty Images)

As you watch some other team hoist the World Series trophy, your mind starts to focus towards the offseason. An opportunity to have newfound hope as you scour free agent list and determine which big name will save your franchise.

“Sign the big bat third baseman and Ace pitcher, money is no issue! Surely these contract will turn out okay.”

Well, maybe they will, or, maybe they will cripple your franchise for half a decade.

The idea of signing the proven star is always fun. However, these contracts are risky. Unlike other major sports, baseball players typically reach free agency around the age of 30, meaning a long-term deal will last into declining years.

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Every player is different. Some play at an All-Star level through their 30s, while others never reach the level you were promised based on previous performance. Today, I want to look at each long-term deal since 2010 and see how they have fared. Some information before we get started:

  • I pulled every free agent deal, not contract extension, that was either five years or more.
  • I started in 2010, and concluded with deals signed before the start of the 2022 season.
  • Each group is broken into good contracts, bad contracts, and you decide categories. I used my own discretion and discussion with other Just Baseball staff to categorize these players so there could be some disagreements.
  • Unfortunately, players who have dealt with injuries are dinged for just that. While it might seem a bit unfair, we have to look at this exercise as a black and white, no grey area. Did the player perform to expected standards – yes or no.
  • Lastly, remember the 2020 season was 60 games, so fWAR numbers might look a little funky for some players

Free Agent Hitters

From 2010 – 2022, 32 free agent hitters signed long-term deals with new teams. These deals range from $60 million (Pollock) to $330 million (Harper). Of the 32 deals, only seven were worthy of the “good deal” category, and five of those deals are not completed. Two deals fell into the “you decide” category, and the rest have been bad deals.

Good Deals

Hey, it paid off! You might notice this list has several players who were signed in more recent years. Obviously, we do not know how the rest of their contract will play out, but they have at least shown early returns and we cannot ignore their production.

I don’t care how much praise we give Adrian Beltre, it’s never going to be enough. An incredible player who performed into his later years. Signed at age 32, Beltre earned three All-Star appearances and three Gold Gloves during this contract.

Martinez was dinged a bit in the fWAR category because he did not play the field much, or very well, but his bat showed up. We’ll see how Seager and Semien age, but they have brought their team a World Series to date.

Freddie Freeman is aging like fine wine. He’s been an All-Star in his first two seasons with the Dodgers and has finished top-5 in MVP voting both years. He rarely misses any games and shows no signs of slowing down.

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You Decide

There’s not much to this category. I viewed these players as fine, and not exactly a catastrophe. Surprisingly, both of the hitters in this category were catchers. It’s hard to compare catchers to other hitters because their primary value is calling pitches and managing a staff, something we cannot quantify with a number.

Both of these players had great careers, and you could even argue McCann could be a good deal. I’d take a 2.5 WAR catcher with pop any day. I’m sure Blue Jays will say Martin was worth the deal. Both ended up being traded with McCann going to the Astros and Martin going to the Dodgers.

Bad Deals

Welcome to the majority. Before we highlight all this slop, I should note that most *super* long deals (8+ years) will not age well.

Teams know that, but the prime years are worth the bad back-end years, or at least that’s what teams convince themselves. I did consider contract amount and expectations when making this list so some players who performed decent, but did not meet expectations, fall here.

Where do we even start. Yasmany Tomas? Ian Desmond? How about the noted baseball lover Anthony Rendon? Pretty remarkable how many of these big-time deals did not even see the end of their contract.

I expect Javier Baez to join that company. Kris Bryant as well. George Springer and Nick Castellanos have a chance to recover some value, but both are headed down a step cliff right now. Trevor Story cannot stay healthy or prove that he was not significantly aided by playing in Coors.

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Free Agent Pitchers

You might think signing pitchers are riskier than hitters due to injury. While that can be true, pitcher signings have “hit” at a much higher rate than hitters since 2010.

A total of 28 pitchers have signed a deal of five or more years since 2010, 13 have been a good signing, three have been a you decide, and 11 have been bad.

Good Deals

Yu Darvish and Zack Greinke each made the list on two different deals. Darvish has finished second in Cy Young voting twice, while Greinke finished top five twice during his deals. You have World Series-winning aces, Cy Youngs, and other decorated pitchers on this list. I was surprised how many “hits” there were on pitchers deals.

Ryu was a steal for the Dodgers even when you consider his injury. Of course, we cannot talk about this list without mentioning Max Scherzer. Back-to-back Cy Youngs, while finishing top five in voting all but one year in Washington. Winning a World Series was the cherry on top.

You Decide

This list is about what you would expect. A solid, three or four in your rotation, innings eater who didn’t break the bank. There’s some mixed results on the list, but overall I feel like the team got enough value, but not exactly more than what they paid for.

Detroit, congrats! You have made the you decide list not once, but twice. Sanchez was great in the beginning of his deal but faded. Rodriguez had a very strange year one, looked like the best pitcher in the league at times in year two, then opted out. It’s hard to really say the deal was a win or a loss, so E-Rod falls here.

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Bad Deals

While there are some disasters on this list, keep in mind I considered expectations when categorizing these players. Some put up fine starts, but fell short of their expectations relative to the deal they were given in free agency.

Jordan Zimmerman might be the worst deal here. At least Corbin performed at some point and fetched a World Series ring. Zimmerman never clicked in Detroit. Sierra is a name I was not familiar with, although the deal was relatively small, $30 to never reach the majors cannot be spun in a good way. Robbie Ray was paid after his remarkable year in Toronto, but injuries have held him back. The chances of him coming back and providing enough value to make the deal worth it are slim.

Price, Samardzjia, and Cueto had their moments but ultimately fell short of expectations.

Success and Failures for Each Team

Of the 30 teams in Major League Baseball, only 19 have a signed a free agent to a five-year deal or longer since 2010. You’ll notice a trend – a lot of small market teams are missing. We can discuss the reasons all day (and if they make sense) but we know those teams cannot stomach failed deals like the larger markets. However, when those teams do spend, it is usually to retain their own players that they have developed.

TeamGood DealBad DealYou Decide
Detroit Tigers042
New York Yankees311
Philadelphia Phillies410
Texas Rangers410
Los Angeles Dodgers320
Boston Red Sox130
Los Angeles Angels 040
Arizona Diamondbacks 120
Toronto Blue Jays111
Chicago Cubs210
St. Louis Cardinals 011
Miami Marlins020
Washington Nationals110
Seattle Mariners020
Colorado Rockies020
San Diego Padres110
San Francisco Giants020
Atlanta Braves010
Kansas City Royals 010

Believe it or not, the Tigers have handed out the most long-term deals. They also have not had a single one qualify as a good deal. The Angels are not far behind going 0-4 in this exercise. The Astros are the only team not to sign a long-term deal and win a World Series in this time frame (2017 & 2022).


Free agency is never a guarantee, but more of a roll of the dice. Several factors play into why a deal doesn’t work. Do players lose motivation once they get paid? A new ballpark plays differently and doesn’t pay them any favors? Really though, father time is simply undefeated.

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The biggest takeaway for me is building a winning team happens through draft, development, and retaining your best players. Free agency is a supplement to a roster and a tool to help you get over the top. If you think you can build a roster off signing big ticket deals, especially as a mid/small market, you might get caught with your pants down.

Deals of this size that fail not only leave you cash strapped, but will also cause hesitation with the front office when considering future deals. I’m not anti- big deal by the way. Sometimes you need to swing for the fences and roll the dice. But, only a few teams can truly afford (both money and risk) more than one long-term deal.