Absolutely agree.

Why would Pedroia settle for a mere $20/year?

What would you suggest it would require to get him to sign?

Prior to the 2012 season, the Rangers had Ian Kinsler signed for one more year at $7M and a 2013 option for $10M. They inked him to a 5/$75M deal that started in 2013, essentially picking up the option and extending him at 4/$65M. 4/$80M seems fairly reasonable for Pedroia, considering he's likely better but further removed from free agency right now.

Don't they already have him through his most productive years? Are we sure we know what type of player Pedroia will be in 2016? I'd want to watch another year before pulling the trigger on him. Spending 20m for a player who might be in decline by then seems to be a mistake.

And take away his children?

Second basemen don't age well. Sandberg was done as an elite player (WAR of 4.0 or higher) at 33, Biggio 32, Alomar 33, Utley 31, Kent 34, Knobby 28, Robby Thompson 31. Of all the secondbasemen since 1980 to have 30 WAR or higher (14 of them), only Lou Whitaker had a season of 4.0 WAR at age 35 or higher. So they have Pedroia for ages 29-31, and a 4 year extension takes you through age 35. That's risky, but I suppose they have to do it for PR reasons if nothing else.

35 isn't sufficiently far beyond the 2B event horizon to worry me. If in a 4 year extension Pedroia is "elite" for 2 years, then merely good for 2 years, it'd absolutely be worth it.

I think Darren's proposal seems pretty reasonable for both parties. And 4/$80M wouldn't end up being terrible even if Pedroia declined into just a "good" player in his 30s either. If you can get 4 WAR consistently for 20M a year, it's not bad. Obviously you hope for more when you sign such a deal, especially if it came this far ahead of his FA eligibility, but that would be a perfectly acceptable result for such a deal.

Not so sure that there will be that many teams eager to pay top dollar for Pedroia in light of his home/road splits:

Home .319/.382/.501
Away .286/.356/.421

He may be worth more to Boston than other teams, and the Red Sox wouldn't seem to be risking that much by waiting. They'll still have the money to do what they want in 2 years.

What is Pedroia going to expect for age 32? 6/$140M?

No thank you.

Signing Pedroia now allows the Sox to sign him through age 34-35 rather than 37-38.

Yes, please.

#7 already covered the "second baseman don't age well" part of this discussion.

The proposal has merit...for the Red Sox. Not sure if Pedroia would go for it though as it would effectively see his last big pay day at 35/36, not the 38/39 he might be expecting.

To clarify, if he's still somewhat useful after 36 and at the end of his contract, I'm sure he'd still get 3/35 or something. But that is half of what he'd get if signed the 6/140 contract that ends when he is 39. He'd essentially lose out about $30 mil for those last 3 years.

The proposal has merit...for the Red Sox. Not sure if Pedroia would go for it though as it would effectively see his last big pay day at 35/36, not the 38/39 he might be expecting.

Concur. If you want Pedroia to accept only 4-years on the extension, he's probably gonna want at least $25M per.

@10, Pedroia's hitting style is uniquely tailored to Fenway. He's a line-drive hitter who uses the whole field. I doubt teams would be too worried about the park.

The proposal has merit...for the Red Sox. Not sure if Pedroia would go for it though as it would effectively see his last big pay day at 35/36, not the 38/39 he might be expecting.

Pedroia's not choosing between those two. He's choosing between getting locked up through 34/35 and waiting 3 years to see what his market is. [On a sidenote, I think you're off on Pedroia's age. He's 29. A 4-year extension takes him through his age 34 season.]

Concur. If you want Pedroia to accept only 4-years on the extension, he's probably gonna want at least $25M per.

No way is $25M the lower limit. I've already provided an example of a Kinsler, who was closer to free agency, coming off a better year, and would reach FA at the same age. He took 4 years at $16M per. David Wright was 2 years younger, 2 years closer to free agency, and his extension was worth about $16-17M/year. Jose Reyes was three years younger and an actual free agent and got $17.5M. It's completely reasonable to think that Pedroia would take a deal that triples his net worth three years before he'll have a chance to test the free agent market.

Prado, 1 year younger, not as good, only 1 year from free agency, signed for something like 3/33 extension.
Beltre was actually at the age Pedroia will be in 3 years and was actually a free agent and signed for 5/80.
Zimmerman was 2 years from free agency, 2 years younger than Pedroia, and he took a 4/74 extension.
Phillips, 2 years older, only 1 year from free agency, took 5/61ish.

No way is $25M the lower limit. I've already provided an example of a Kinsler, who was closer to free agency, coming off a better year, and would reach FA at the same age. He took 4 years at $16M per. David Wright was 2 years younger, 2 years closer to free agency, and his extension was worth about $16-17M/year. Jose Reyes was three years younger and an actual free agent and got $17.5M. It's completely reasonable to think that Pedroia would take a deal that triples his net worth three years before he'll have a chance to test the free agent market.

Reyes and Wright go six-year and seven-year deals respectively.

I think you could get Pedroia for 6/120 in a heartbeat.

Both guys were considerably younger than Pedroia and way closer to FA, and yet neither even cracked $20M/year, much less $25M.

Putting that aside though, can you explain how it's going to take at least 4/100 to get Pedroia (so presumably more like 4/110?) but 6/120 gets it done in a heartbeat? That doesn't sound right to me.

Also, what do you think Pedroia's market value will be after 2015?

I am generally under the impression that Pedroia's lack of tools / scouty pedigree makes him an easier sign than the typical ballplayer with his batting average and WAR. I could be wrong, certainly, but I think Darren's guesses at expected contracts are reasonable.

It seems like this type of thing never happens, but wouldn't guaranteeing 2015 and then tacking on just one more year (at big money) be attractive to both the team and Pedroia?

I don't think it would be attractive to Pedroia. I think he'd rather hit free agency a year earlier and get the bidding going as a 32 year old (after 2015) than as a 33 year old after 2016. The only way it makes sense is if Pedroia think he's going to collapse in his age 31 season and even in the highly confident group of people that make up MLB players Pedroia sticks out as a confident guy.

The only way it makes sense is if Pedroia think he's going to collapse in his age 31 season and even in the highly confident group of people that make up MLB players Pedroia sticks out as a confident guy.

By the same logic, the only way it doesn't make sense is if Pedroia thinks he's going to collapse in his age 32 season.

I.E. if Pedroia thinks he will get a big payday after his current contract, he probably thinks he could also get a big deal with his free agency happening one year later.

No, Pedroia makes more money if he can sell his age 31 season at the front end of the contract. Even if he doesn't collapse, he'll get more money after his age 30 season than he would after an equivalent age 31 season. Players never take short-term buyouts like that to delay free agency.

Even if he doesn't collapse, he'll get more money after his age 30 season than he would after an equivalent age 31 season.

Right, but to make up for that would be the big age 31 salary and, more importantly, to get that guaranteed now (as well as getting the option year guaranteed now).

For example (with hypothetical numbers): If everything goes well he could get $100/5 after his current deal. If he took a $27 million 1-year extension, he would only have to get $73/4 a year later to match the salary - but more importantly he would have a hedge against his value plummeting in the next 3 years. The only way he would "lose" would be if his value happened to plummet in that one year (or he becomes a better player in the next 4 years).

i'm not totally convinced the yanks are going to re-sign cano, which drives up his bidding even further. if you've got any of the few other "elite" 2b, you need to lock them up because cano will drive the price up, and the yanks might be poaching for a 2b to replace him, both with money and with a trade. kinsler, for example, is in the same category as pedroia. and that's ignoring all the good points made by the post. absolutely agree with the post.