Evan Longoria  said at a press conference announcing his six-year, $100 million extension (which will functionally turn his current contract into a 10-year, $136 million pact with the Rays that runs through 2022) that the free agent market never really enticed him, and that he’s hoping to become the first wire-to-wire member of the Rays in franchise history. He was willing to leave potential money on the table in pursuit of that outcome.
Had he concluded his original contract — signed just days after his big league debut in Tampa Bay — in good health while maintaining his career performance to date, then at age 30, the gifted third baseman might well have commanded a contract for nearly double the $100 million he’s been guaranteed by the Rays. But in order to secure a nine-figure deal a full four years before free agency, and to stay with the only franchise he’s ever known, that was a sacrifice Longoria was prepared to make, and one that, from the team’s vantage point, he had to make. There is, after all, considerable risk for a team in making a commitment that does not start until 2017.
The Sox, of course, have their own homegrown franchise cornerstone in Dustin Pedroia , and like Longoria, he jumped in with both feet to sign up long-term with the Red Sox  early in his career. The second baseman, shortly after he was announced as the winner of the 2008 AL MVP, agreed to a six-year, $40.5 million deal that runs through 2014 and includes an $11 million (with a $500,000 buyout) for 2015.
Had he passed on the opportunity to sign a long-term deal, Pedroia would have been a free-agent this offseason. Instead the Sox have him under team control (assuming the option is exercised) for three more years at $31 million — an extraordinary value for the club.
As it currently stands, assuming (again) that the Sox would be inclined to exercise their option (a no-brainer), Pedroia is positioned to reach free agency after his age 31 baseball season (he will turn 32 in August 2015). Red Sox GM Ben Cherington, in an interview earlier in November on the Dennis & Callahan show, cited Pedroia’s deal as an example of a successful long-term commitment and hinted that the team would like to retain him beyond its current commitment.
“He signed it as a [pre-arbitration-eligible] player,” said Cherington. “Obviously, that deal is going to work out well for the Red Sox and we hope Dustin’s here for a long time.”
However, as Longoria’s considerable increase in average annual salary suggests, the difference between a deal that is signed prior to a player’s eligibility for arbitration and when he is contemplating his potential free-agent earnings is drastically different. Still, given the distance from free agency, it’s also fair to suggest that, like Longoria, an extension for Pedroia would look quite a bit different than one signed by a player who was on the cusp of free agency (as when Cole Hamels signed a six-year, $144 million extension with the Phillies this summer, months before he hit the open market).
There are now a few examples of extensions layered upon long-term deals that offer some guidance as to what a Pedroia deal might look like, with Longoria’s second long-term deal with the Rays representing the latest example.
Thanks to the magic of the transaction tracker on MLBTradeRumors.com, here’s a quick look at Longoria and the other position players who, since the start of 2007, signed a second multi-year deal with a team while still multiple seasons away from free agency (the scenario that Pedroia and the Red Sox would face either this winter or next):
Evan Longoria, Rays: 6 yrs, $100 million ($16.67 million AAV) — 2017-2012, signed 4 seasons before free agency, ages 31-36
Ian Kinsler , Rangers: 5 yrs, $75 million ($15 million AAV) — 2013-17, signed 2 seasons before free agency, ages 31-35
Joey Votto, Reds: 10 yrs, $225 million ($22.5 million AAV) — 2014-23, signed 2 seasons before free agency, ages 30-39
Troy Tulowitzki , Rockies: 6 yrs, $118 million ($19.67 million AAV) — 2015-20, signed 4 seasons before free agency, ages 30-35
Ryan Zimmerman , Nationals: 6 yrs, $100 million ($16.67 million AAV) — 2014-19, signed 2 seasons before free agency, ages 29-34
Ryan Braun , Brewers: 5 years, $105 million ($21 million AAV) — 2016-20, signed 5 seasons before free agency, ages 32-36
Ryan Howard , Phillies: 5 years, $125 million ($25 million AAV) — 2012-16, signed 2 seasons before free agency, ages 32-36
Michael Young, Rangers: 5 years, $80 million ($16 million AAV) — 2009-13, signed 2 seasons before free agency, ages 32-36
David Ortiz , Red Sox: 4 years, $52 million ($13 million AAV) — 2007-10, signed 2 seasons before free agency, ages 32-35
A few thoughts:
- Kinsler offers the lone second baseman in this group who signed a second extension with a team more than a season away from the conclusion of his first. His $15 million AAV is also the highest ever given to a second baseman, so his deal would represent a likely baseline for conversations between the Sox and Pedroia. Of note: The five-year deal replaced Kinsler’s option season; the Sox could certainly pursue a similar approach to Pedroia’s option year in order to keep the length of the deal to five years.
- It’s also worth mentioning one second baseman not on this list: Brandon Phillips , the Reds second baseman who signed a six-year, $72.5 million extension in April, just before playing out what would have been the walk year of his contract. Though characterized as a six-year, $72.5 million deal, it only extended his deal for five years while adding about $60.5 million to what he was already slated to earn.
- The Red Sox got an excellent deal in the Ortiz contract, though it’s worth pointing out that until Ortiz negotiated a second long-term deal with the club, the team held a $7.75 million option on him for 2007, so he did boost his salary by a not-insignificant amount for that season.
- In terms of ages, all of the deals except for Votto’s expire by the players’ age 36 seasons, and in some cases, earlier.
- In terms of length, all of the deals except for Votto’s and Ortiz’s were for five or six years, with teams gaining an extra four to six years of player control.
- For the most part, there’s not much data upon which to judge whether these deals will end well or poorly for the teams. Young is the one player who signed a second long-term deal with his team while still years away from free agency; he’s alternated All-Star-caliber years with disappointing ones during the first four years of his contract, though it should be pointed out that he signed the deal as a shortstop, and has since become more of a corner infielder/DH type, and the Rangers made a number of attempts to trade him. Howard’s deal looks like a cautionary tale, both in terms of the dollars committed and in terms of the risk that the first baseman represents. He blew out his Achilles in October 2011, just before the contract took effect; he thus missed much of his first year of the deal, and all signs point to diminishing production for him.
What to make of this list? Tough to say, given how few players have signed multiple-year extensions well before the conclusion of their first long-term deal. However, assuming that an extension for Pedroia would replace the Sox’ option year of his contract (and thus begin at age 31), the terms of Longoria’s deal might actually represent a fairly reasonable area for discussion between the Sox and Pedroia.
Such a deal would make him the highest-paid second baseman ever (at least until Robinson Cano  signs his deal) in terms of both total contract size and AAV while allowing the Sox to avoid extending his deal beyond a point of comfort regarding the second baseman’s age. Moreover, given that baseball is in an inflationary period with explosive growth in TV revenues, extending Pedroia now could allow the team to lock him up before salaries for second basemen, led by Cano, hit the $20 million mark in AAV.
If the Sox are confident that Pedroia can stay reasonably healthy into his mid-30s — not necessarily a given, because of his relentless, no-holds-barred style of play — then a deal like Longoria’s might make sense for both Pedroia and the Sox. At the very least, with Longoria’s deal, both the team and player received another data point about a rare class of players that Pedroia hopes to join.