The 2017 Free Agents Who Could Have Been

You have a choice. Either I give you $100 right now, or you can let me flip a coin. If the coin lands on heads, I’ll give you $250. But if it lands on tails, I’ll give you $20. I’m using a fair coin, so the expected value of flipping the coin is $135 based on the 50/50 odds it lands on heads or tails. If you like risk or are a risk-neutral person, it’s an easy decision to take your chances with the coin because the odds are strongly in your favor. If you’re a risk-averse person, however, you’re more likely to take the sure thing because $135 isn’t a whole lot more than $100, and $100 is a whole lot more than $20.

Let’s add another wrinkle. It’s the same choice, but if you choose the coin flip, you have to wait a month. The dollar amounts are the same, but now there’s a time component. To get the value of the coin flip, you need to apply a discount factor to the $135. For some people, that discount factor is pretty close to one, but it might be much lower if you’re strapped for cash and the $100 would dramatically improve your life in the present.

Major-league players face a much higher stakes version of this decision when their club comes to them with a contract extension. Do they take a sure thing now, or do they wait and gamble on themselves? While we’re focusing a lot on the 2016-2017 free-agent class this month, there are 13 players who could have been free agents for the first time this year but instead chose to cash out early by signing extensions. Did they make the right decision?

Before we go any further, we have to recognize we can’t actually determine if they made a good decision or a bad decision, we can only estimate about how much money they gained or lost by signing their deals. We have no way of knowing how risk-averse players are or how large their discount factor is. Leaving $50 million on the table seems like a really bad call, but if locking in a big payday early and getting an influx of cash greatly improved a player’s family’s quality of life, it was probably a fine decision.

Using Baseball-Reference’s contract pages, I identified 13 players who currently have between 6.000 and 7.000* years of service time who are not free agents this winter and have never been free agents (i.e. previous non-tenders are excluded). In other words, these are players who would have hit the market for the first time after 2016 had they not signed contract extensions earlier in their careers. I also excluded Stephen Strasburg because he signed his extension during the 2016 season.

*The three digits after the decimal point represent days.

Our task is to consider how much they would have earned this winter and to compare that to what they will be paid over the rest of their current deal. We’ll also keep an eye out to see if any of the players made more money during their arbitration window than we would have expected if they went year to year. Keep in mind, my estimates are just that — estimates. I’m trying to fit the years and salaries into the context of the market so far, but there are a couple of players who would stand out as unique free agents.

I’ve broken the players down into two categories based on whether signing the extension was good/neutral or bad for their overall financial well-being. Obviously, as you’re reading this, remember that a dollar secured in 2013 has more valuable than one in 2017. But I won’t make any precise estimates for that because each player has their own ideas about risk and the time value of money. To the list!

Good/Neutral Extensions

Francisco Cervelli, $31.0M (2017-2019)

When the Pirates inked Cervelli to a three-year extension before the 2016 season, it looked like a tremendous steal. Cervelli was coming off a 3.8 WAR season and one of his most impressive skills, pitch-framing, is not included in our version of WAR. He didn’t have a long history of durability and success, but he seemed to be a good defensive catcher with a solid bat. That kind of talent would easily break $31 million.

However, Cervelli came back to Earth in 2016, hitting just one home run in 393 plate appearances. His patience at the plate and defensive skills remain, but given that teams haven’t traditionally paid a ton for framing, Cervelli probably didn’t end up leaving a ton of money on the table.

Starlin Castro, $60.0M (2013-2019), $16.0M option

If you can believe it, Starlin Castro still hasn’t turned 27. He’s had an up and down career and is coming off a 1.1 WAR season with the Yankees. Castro is due $46 million over the next four seasons if his 2020 option is exercised and it’s hard to see him significantly blowing past that amount, especially considering that he probably banked a couple extra million dollars above what he would have made in arbitration thanks to the structure of his extension.

Yet Castro is an odd case because he clearly possesses significant raw talent, even if his lack of patience and defensive shortcoming have held him back even in his best seasons. It’s not that difficult to imagine a couple of teams seeing Castro as a candidate for growth in his late 20s and offering him a bit more than he has left on his deal, but I don’t see a realistic scenario in which Castro would earn a significant amount beyond $46 million.

Michael Brantley, $25.0M (2014-2017), $11.0M option

Brantley is obviously good enough to be worth more than the $18 million he could earn over the next two seasons, but his injury history over the last two seasons would likely tank his free-agent value this offseason. It wouldn’t shock me if a team invested more than that in Brantley in our hypothetical world, but he played in just 11 games this season and it’s not clear in what condition he will arrive at spring training.

Brantley finished in the top three of MVP voting in 2014 thanks to his 151 wRC+ and followed it up with a 3.7 WAR season in 2015, but he would probably be a pillow-contract candidate this winter and locking in his first life-changing paycheck was probably the smart move. This way, Brantley has two seasons to rebuild his value and hit the market at 32.

Giancarlo Stanton, $325.0M (2015-2027), $25.0M option, opt-out clause

It’s very likely that Stanton’s 2016 season was a blip and not a sign that he’s entering his decline phase, but it’s also hard to imagine he’d find a way to make significantly more than the $325 million he could make over the remaining 12 years of his deal. Here’s what our basic contract model says for Stanton, starting with his 2017 Steamer projection:

Essentially, Stanton is in line to earn almost exactly what our simple model suggests, but the model is not factoring in the value of his 2020 opt out, which would decrease the value at least several million dollars. Teams know not to take a single season too seriously, but it seems likely that Stanton’s 114 wRC+ this year would soften his market just a bit, even if he would still break $250 million easily. Barring a dramatic change in the CBA or financial position of the league, it seems unlikely that Stanton would have blown past the value of his extension this winter.

Bad Extensions

Chris Stewart, $3.0M (2016-2017), $1.5M option

It’s a little jarring to go from Stanton’s hundreds of millions to the roughly $3 million Chris Stewart is owed over the next two seasons, but in this weak free-agent market he would easily have made a few million more. Stewart is no one’s idea of a great hitter, but he’s a very good defensive catcher. Stewart makes the bad list primarily in terms of ratio. He didn’t leave more than a few million on the table, but even getting a two-year, $7 million deal this winter would be more than double what he is owed.

Josh Tomlin, $5.0M (2016-2017), $3.0M option

Tomlin is no one’s idea of an ace, but he’s probably around a 1.5 WAR starter next season and the going rate for that kind of player is more than the two-years and $5.5 million he’s set to make from 2017-2018. At the very least, something like two years and $12 million would be a starting point. Much like Stewart, it’s not the raw dollars as it is the ratio of dollars guaranteed to dollars potentially earned on the free agent market.

Craig Kimbrel, $42.0M (2014-2017), $13.0M option

Kimbrel remains a very good reliever, but he’s no longer one of the guys you list when you’re counting down the best five or six relievers in the game. If he had hit the market after 2014, he’d have blown away the records for reliever contracts, but he’s looked a little more human since moving to San Diego and Boston over the last two seasons.

That being said, Kimbrel is still an above-average reliever at worst and a very good reliever at best. Someone with his history would easily fetch more than the two years and $26 million he’s owed over the next two seasons. At the very least, he’d probably get four years at that rate and it’s possible I’m underselling both Kimbrel’s current abilities and the league’s interest in late-inning relievers.

Carlos Santana, $21.0M (2012-2016), $12.0M option

This one is easy. Santana is set to earn $12 million in 2017, which is less than the qualifying offer and far less than he would make on the open market. While his batting average often causes some annoyance among certain fans, his patience and power make him a significant offensive threat. Santana’s floor would probably be $60 million this winter, but it wouldn’t surprise me if teams pushed closer to $80 million over five years for the switch-hitting slugger.

Jonathan Lucroy, $11.0M (2012-2016), $5.3M option

This one is somehow easier than the Santana call. Lucroy is going to make less than $6 million in 2017 despite being one the better catchers in baseball. He had a down year in 2015, but his 2016 campaign showed that was a blip rather than a trend. Even if you’re buying his bat at the 110 wRC+ projected by the Steamer, he’s still probably a 4 WAR player in 2017. A conservative estimate would put his value over $80 million on a four-year deal, and could easily push $120 million or more if teams were confident in his health.

Lucroy, like Santana, mostly bought risk when he signed his extension. As long as he stays healthy and productive in 2017, he’ll make plenty of money next winter and the loss of value will only come from the difference between his potential 2017 salary and what he actually earned. The real loss comes in the form of the added risk he’s taking on by playing an additional season without signing his first free-agent deal.

Freddie Freeman, $135.0M (2014-2021)

Another easy case. Freeman is entering his age-27 season coming off a 152 wRC+ and 6.1 WAR season. Even if his power comes back to Earth, he’d be a lock to earn more than $107 million he has coming his way over the next five seasons. Eight years and $250 million wouldn’t be out of the question for Freeman, so it’s quite clear that signing the extension when he did cost him a significant amount.

Chris Sale, $32.5M (2013-2017), $12.5M option for 2018, $13.5M for 2019

We could take our time to come up with a really accurate estimate of Chris Sale’s value at the moment, but there’s probably an easier short cut. Sale is set to earn $38 million over the next three seasons. Last winter, David Price and Zack Greinke signed for over $200 million. Sale is younger than both and it would be hard to argue he’s any worse than they are on the mound. Fortunately for Sale, as long as he remains healthy he’ll earn himself quite the payday after the 2019 season.

Madison Bumgarner, $35.0M (2013-2017), $12.0M options for 2018-19

Bumgarner isn’t quite as good as Sale, but he’s roughly the same age, has roughly the same money left, and has plenty of postseason heroism under his belt. He probably wouldn’t beat Sale on the open market, but that’s not really the question. Bumgarner would blow past the $36 million he has left on his deal if he were a free agent this winter. Our contract tool thinks seven years and $250 million makes sense for Bumgarner, but even if you move the needle a bit in either direction, it’s clear he signed away significant earning potential when he agreed to his extension.

Buster Posey, $167.0M (2013-2021), $22.0M option

You can certainly forgive Posey for signing a contract worth nearly $200 million after just three-plus seasons in the majors. After all, Posey’s 2011 season was cut short by a nasty injury suffered during a collision at home and given the toll catching takes on one’s body, locking in a small fortune was the prudent move. Yet since Posey signed the deal he’s averaged roughly 5 WAR per year and shows no signs of slowing down.

Posey wouldn’t have much trouble finding someone to pay him $180 million over six years this winter, which is significantly more than the $130 million or so he can earn on the remainder of his deal with the Giants.

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It’s important to keep in mind that none of these deals were necessarily bad decisions by the players who signed them, just that most of the players who signed extensions probably could have wound up earning more if they had taken their chances. That’s an important difference. These players received significant financial security, essentially insuring themselves against injury and unexpected decline.

Yet this is the second year I’ve done an article like this and it’s the second year I’ve been struck by how few of these extensions wind up working in the players’ favor. Even the ones I marked as player-friendly this year weren’t particularly bad for the clubs. Collectively, the players are leaving a lot of money in the pockets of ownership because they value security. I’m a risk-averse person and I fully appreciate that, but perhaps the Players’ Association needs to step in and help balance this structure.

Insurance policies, like the one purchased by Max Scherzer, seem like a reasonable way to make sure individual players aren’t taking on too much risk while also ensuring that the players as a whole are earning as much as possible. It seems that most of the time when a team decides it wants to extend a player before they reach free agency, the dollar figure on which they settle winds up benefiting the club. Players need either to start asking for more before they sign on the dotted line or to take their chances playing it out to free agency more often. That’s not an easy thing for any individual to do, so it’s likely up to their agents and the union to facilitate a system that makes such a decision easier.