Did Michael Bourn & Scott Boras Wait Too Long?

Josh Hamilton got $125 million. B.J. Upton got $75 million. Angel Pagan got $40 million. Shane Victorino got $39 million. Melky Cabrera got $16 million. And Michael Bourn, the best center fielder still on the board — at this point, he’s probably the best free agent position player left, period — is still waiting for the right offer.

In the meantime, many other teams that looked like a good fit for him have filled center field with another player: the Nationals traded for Denard Span, the Phillies traded for Ben Revere, the Athletics traded for Chris Young. In the meantime, bloggers like Martin Gandy of Talking Chop, the SBNation Braves blog, are starting to wonder whether Bourn will need to take a one-year offer and wait ’til next year for his payday. So did Bourn wait too long? Did Scott Boras, gasp!, make a mistake?

I doubt it. Scott Boras is famous for getting his clients to wait until the last minute. At the beginning of the offseason, Bourn was one of many intriguing free agent possibilities. Now, he’s one of the only impact players left, and that has value. As a matter of fact, of all of Boras’s impact free agents to get big multiyear deals, virtually all of them signed it in December or January. (I’m ignoring his big-dollar extensions, because the timing on an extension is very different from the timing on a free agent.)

Here’s a table of many of his biggest free-agent deals. I put this together by hand so I’ve undoubtedly missed several; please let me know in the comments.

* The Red Sox paid a $51.1 million posting fee for Matsuzaka on November 16, 2007, and had 30 days to complete a deal. They completed it on the 29th day.

Now, those are his greatest successes, and lest I fall in the trap of sampling on the dependent variable, I had better note some of the times when he failed to get a rich multiyear deal for one of his clients.

In the 2009 offseason, Adrian Beltre was coming off a disappointing contract year in Seattle, and he didn’t receive any offers that Boras felt were worthy of his talents. So, on January 5, he signed with the Red Sox for one year and $10 million, hit the cover off the ball, and got an $80 million deal 12 months later. That was a rousing success. Other one-year deals didn’t work out as well.

Edwin Jackson was looking for a multiyear deal in the 2011 offseason. As Mike Axisa wrote back in August:

[Jackson] did in fact receive a multi-year offer, a three-year contract worth more than $30 million from the Pirates according to Ken Rosenthal. He instead opted for the one-year pillow contract, a Scott Boras specialty.

Jackson signed that one-year contract on February 2, 2012. Today, he signed for $52 million over four years.

Carlos Pena has been in this situation quite often in his career. Coming off a three-year, $24 million contract in the 2010 offseason, Boras tried to build his value with a one-year “pillow contract,” as Pena signed a one-year deal with the Cubs on December 8, 2010.

But it didn’t work; since then, Pena has signed two subsequent one-year deals, for less money each time. He signed a one year, $7.25 million contract with the Rays on January 23, 2012, and then he just signed a one year, $2.9 million contract with the Astros on December 17, 2012.

In the 2011 offseason, Ryan Madson appeared to have a 4 year, $44 million contract on the table from the Phillies, but it fell through. He signed a one-year, $8.5 million contract with the Reds (it was $6 million in 2012, then a mutual option with a $2.5 buyout for 2013).

Of course, Madson blew out his elbow and missed the whole year, and had to content himself with a one-year, $3.5 million contract with the Angels. Shockingly, he signed that on November 28, 2012, the earliest that I have seen a Scott Boras free agent sign.

So, considering that Boras has such a well-established pattern of holding his free agents late in the offseason, why does it continue to be effective for the majority of his high-profile free agents? How is it that, twelve years after the Alex Rodriguez contract, where he famously convinced Rangers owner Tom Hicks to bid against himself, Scott Boras is able to get such a high value for most of his elite free agents?

Boras’s pattern is so well-known that a year ago, Jerry Crasnick wrote a column about this exact tendency of his. Crasnick quoted one NL executive as saying, “You have to marvel at his smarts and all that. But eventually, if you don’t change the plays, the defense stops you. And he keeps running the same plays.” However, another executive said: “But who knows? The amazing thing is, somehow he always seems to get them the money.”

The key is that scarcity runs in two directions. On the one hand, there are only 30 teams in baseball, and there is a limited number at any one time who will have a pressing need for a free agent at a given position. On the other hand, there are a very limited number of impact free agents.

Boras is willing to run out the clock and let the number of possible destinations dwindle because he relies on the fact that good free agents become increasingly scarce as the offseason wears on. He plays on the insecurity and sense of panic that teams start to feel as they approach the season and don’t feel happy with their teams as currently constructed.

After the trading flurry at the winter meetings, after many of the biggest-profile names have signed their contracts, there’s almost always a Boras client still on the board in December or January, and he’s usually the best player available at that point — and often, that Boras client has been the best free agent available all offseason.

There are almost always a few teams willing to pay a premium for a player like that, in the hopes that they’ll be able to basically score unanswered points against their division rivals. Boras realizes that the offseason is dynamic, and preys on teams who have been disappointed in their plans to upgrade their teams. His players often represent a last-ditch effort to upgrade a team after lower-cost creative options (like Denard Span) have already come off the board.

He occasionally outsmarts himself, as he may have done with Madson, and most famously of all with Matt Harrington. The Boras waiting game doesn’t always work. But all the same, it’s been pretty damn effective over the years. I wouldn’t bet against Boras — or Bourn.

UPDATE: Apparently, Edwin Jackson just signed a four year, $52 million deal with the Cubs. So the Scott Boras strategy — signing a one-year contract and then waiting till late December — clearly paid off for him, even though he’s no longer a Boras client.