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Is there a best time for free agents to sign?

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Some believe that setting the market can earn a free agent the most money. Others, however, believe that waiting out the market can get the biggest buck.

MLB: Spring Training-New York Mets at Boston Red Sox
Pablo Sandoval signed his long-term contract in November, and he earned a big payday. Is this the way to go?
Kim Klement-USA TODAY Sports

Looking at and charting every single Major League guaranteed signing over the past five offseasons is not easy. In fact, it makes you exhausted. I speak from experience.

I just built a spreadsheet that has all that data. Lucky for me, it was pretty easy to find, thanks to MLBTradeRumors.com’s transaction tracker. But now, I have to put it to use.

Since I began to cover baseball seriously a few years ago, free agency has always interested me more than just about anything else. In no other sport (perhaps excluding the NBA, but even still, the max contract hinders that) do the best players get to truly choose their destination. Money flies everywhere. Teams open their pocketbooks to extraordinary heights.

Over the past five offseasons, teams have spent almost a combined $10 billion on Major League free agents. That could buy the New York Yankees three times over, according to Forbes. And it could buy the Tampa Bay Rays 15 times over.

I have always wondered, though, what the best time is for a free agent to sign.

I asked five baseball agents to imagine that they had an average client who was a free agent. I told them that all other factors are the same. Then, I asked them to rank November, December, January and February in order of when they believed they would find the highest contract value for their player.

Here’s how they voted:

Agent #1 Agent #2 Agent #3 Agent #4 Agent #5
1st December December December December December
2nd November November November January November
3rd February January January November January
4th January February February February February

Thanks to that computer class I took in middle school, I was able to crunch the numbers for every signing over the past five years pretty easily. After dividing it out with amount of contracted years, I was able to find the average annual value for each month. Here’s how that panned out:

November $8,434,958 / year
December $9,651,500 / year
January $9,400,350 / year
February $5,839,307 / year

Of course, there’s a lot to unpack here. The Winter Meetings take place each December, so that month ranks first in terms of annual average value. Most of the best free agents of the past five years, including David Price, Zack Greinke (twice), Jason Heyward, Jon Lester and Robinson Cano have signed in December.

But the theory that the best free agents sign early seems to be slightly debunked by the fact that players have earned, on average, $1 million more by signing in January than in November. And, it’s also worth noting that the discrepancy between December and January isn’t too large either, at just over a 2.5 percent difference.

Still, when we look at the numbers even further, January 2016 blew all its counterparts out of proportion. While the other four Januaries ranged in guaranteed dollars from $100 to $300 million, January 2016 saw over $700 million guaranteed, due to contracts given to Justin Upton ($132.75M), Chris Davis ($161M), Wei-Yin Chen ($80M), Yoenis Cespedes ($75M) and Alex Gordon ($72M). Obviously, it is an outlier.

In fact, that’s the only year where the league’s January spending was greater than their November spending. But I don't think it is completely dismissible data, either. Max Scherzer signed a $210 million contract in January 2015, Matt Garza got $50 million in January 2014 and Edwin Jackson and Nick Swisher each got over $50 million in January 2013. There is still money to be had in January.

Still, those players are (or were at the time) among the better of those free agent classes. What about the average MLB free agent? What month is the best for him to sign? This is a much more important question, considering the fact that Max Scherzer was probably going to get at least $175 million whether he signed in January or on the first day of Spring Training.

FanGraphs defines a solid starter as a player worth 2-3 fWAR. So what 2-3 fWAR player earned the best bang for their buck?

A Case for November: Five years, $95 million; Pablo Sandoval; 2.9 fWAR; November 2014

Two years later, Sandoval’s contract might already be one of the worst in baseball history. He was a productive player the year before, but at 2.9 WAR, he should not have earned close to the $20 million per year figure the Red Sox promised him. While Sandoval was one of the hottest names on the market during that offseason, if he had signed later and with fewer suitors, it’s hard to expect him earning the same salary.

A Case against November: Two years, $17 million; Russell Martin; 2.0 fWAR; November 2012

To be fair, Martin signed this contract before the value of pitch framing was truly established. Still, though, he was coming off a season hitting 21 home runs with a .311 on-base percentage, both marks that are not terrible considering his positional value. His conventional defensive statistics weren’t bad either, as he threw out runners at a fairly solid clip. Teams were looking at that data (or at least they should have been). Could he have waited later in the free agent market and earned more money? I think so, especially as the market continued to simmer.

A Case for January: Five years, $80 million; Wei-Yin Chen; 2.7 fWAR; January 2016

Wei-Yin Chen’s contract still makes me shake my head to this day. Chen was a good, not great pitcher for the Orioles, and he landed a contract worth $16 million per year. He made more guaranteed money that offseason than Yoenis Cespedes, Ben Zobrist, and Alex Gordon. Yes, those are all position players, but it still shows that Chen’s waiting for David Price, Johnny Cueto and Zack Greinke to sign really paid off. The Marlins were desperate to add a starting pitcher, and the ball was in Chen’s court to make the pretty penny.

A Case against January: One year, $5 million; Mike Napoli; 2.0 fWAR; January 2013

Marco Scutaro, also worth 2.0 fWAR in 2012, got a three-year, $20 million contract in December. Napoli’s versatility was obviously way worse than Scutaro’s at the time — as was his physical — but he was also six years younger and coming off a season with 24 home runs and an .812 OPS over 417 plate appearances. Again, like all these other examples, it’s impossible to know whether Napoli would have earned more money signing earlier, but it is possible he took less money to figure out where he was playing in 2013 and go from there.

All in all, I’m trying to simplify a very complicated process. Free agency has many variables, including the supply at a position, the trade market and draft pick compensation. But I have always wondered when the best time was for an average free agent to sign.

There are two schools of thought. One believes that signing early could get a player the most amount of money before teams can see the real asking price for that position. The other, however, thinks that waiting until teams are more desperate could pay dividends. And, of course, it depends on the player, and on the teams interested. That’s why it is virtually impossible to put a finger on a month and call it the best time to sign.

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Devan Fink is a contributor at Beyond the Box Score. You can follow him on Twitter at @DevanFink.