Boston Herald:

What would potential deals for these three look like?

I'm not sure what potential deals would look like, but I'm almost certain that all three players have been reluctant to have their remaining years bought out. The Sox would have to break the bank to get them to sign a long term deal.

The Globe took the same comments and said Bay and Lester are the logical possibilities to be signed.

Of the 5 players (across the 2 different papers' reports) mentioned for extension, I think it breaks down like this:

Lester: Given the inherent risk as a pitcher he's probably the best candidate to accept a "set for life first multi-million $ contract" at below market value. (I'm thinking along the lines of Haren's first deal.)

Paps: Would probably be a candidate for the above if he would accept it. All his public statements seem to indicate that he would prefer to go year to year to maximize his earnings rather than accept less in exchange for lesser risk.

Pedroia: Probably the best bet among the position players to accept a long term deal that buys out a few FA years. He's young enough that even with a few years of FA bought out he would still hit the market at the back of his prime years, so the Sox could really offer a much longer deal. (He'd probably get a deal similar to what Cano got last year, perhaps a little better.)

Youks: He's older and coming off of a contract year. He's close enough to FA that it's probably not worth it to him to accept a below market deal.

Bay: Is only really worth it if he takes a deal that is below market value in $/yrs. Since we saw that his defense isn't really saving the amount of runs you'd like I could easily see the Sox attempting to switch out Bay with Holliday after next year ala OCab for Renteria. Holliday looks like a better hitter and his defense has been very good for the last couple years as well. If the team can't get a discount it makes more sense to pay more for the elite talent.

Wasn't Papelbon shooting off his yap in spring training about wanting a long term deal NOW? His status as an elite closer earned it, Fruitbat, blah blah blah...?
The article includes Pedroia as arb-eligible; Cot's is listing 2.121 yrs service time as the lowest potential Super Two, and Pedroia is only 2.041.

He wants a long term deal, he just didn't think that he should give the Sox any kind of discount for the extra risk they would assume. He basically wanted to be paid like a free agent despite having less than 2 years of service time. I think he backed off those comments a bit later, probably after his agent gave him a quick explanation of baseball contracts 101.

I don't think the numbers bear this argument out. Three-year (2005-07) road OPS for both guys was identical, .856. Bay was .867 at Fenway this year, and Holliday ws .891 on the road this year.
Bay's range factor and field percentage are both higher than Holliday's. Plus, we know Bay is well-suited in Boston.
This argument, to me, looks like the definition of violating the "if it ain't broke, don't fix it" rule.

This ignores two important factors w/r/t Holliday. First, the road numbers of Rockies hitter tend to be a poor analogue for their performance once they move to another team. The evidence shows that the real mashers on that team generally put up better numbers on a full year basis playing for other teams than their road numbers while on the Rockies would suggest. This is likely due to the need to make substantial adjustments from one series/game to another as you move back down to sea level. That said, the data points here are admittedly polluted by the steroid era guys (Bichette, Burks, Gallaraga, etc..), so who knows if it's reflective of reality. More importantly, Holliday has displayed an unmistakable upward trend in his road OPS in each year of his career. Hear are his road OPS splits:

2004: .654 (platooned that year)
2005: .729 (started 121 games/quasi platoon)
2006: .819 (first year as a full time player)
2007: .860
2008: .892

You have to like the direction this is moving. While some of the luddites here may think that his .654 road OPS as a 24 year old platooning rookie are relevant to the discusion, I don't. In a post-steroid world where stud power hitter are tougher and tougher to find, Holliday seems like the real deal to me. He'll cost a lot more than Bay, but from a production standpoint, I don't think Bay can hold Holliday's jock.

Just taking their respective defense into account, over the last 3 years Holliday is +3 (enhanced plays) via +/-. Over the same time period Bay is -20. Furthermore Bay is trending down, having 2 bad years after a good 2006 (by this metric) whereas Holliday has been improving each year, culminating in a very good year this year.

For comparison Manny was -68 in the last 3 years.

Bay just doesn't seem to get a good read on the ball coming off the bat, so that could be reflected in his fielding stats.




As far as Papelbon goes, he believes he's already forfeited millions in career earnings by leaving the rotation for the pen. He will not be very amenable to any further discounts.

It was his choice to go back to closing. He's the one who pressed for it; the Sox preferred him as a starter. He didn't seem to have a good grasp for the way arbitration worked at the beginning of this season when his contract situation came up; hopefully he has a better one now.

Well then maybe he shouldn't have walked into Tito's office during ST 2007 and asked to be placed back in the closer's role.

As stated above, the numbers do not bear this out.



He improved his production up through the age of 28, culminating in an mid-prime age 28 season where he had virtually the same OPS+ as Bay (139-130). Most players get better as they reach the age 27/28 seasons. After that, they don't normally continue to improve. Actually, if you look at OPS+, Holliday's 26-27-28 seasons look an awful lot like Bay's 25-26-27 seasons.

What support is there for the concept that Holliday is so much better than Bay that the Sox should ignore the fact that Bay is cheaper and has already shown he can handle playing in Boston? Holliday projects as a little bit more productive hitter, but not by enough that the Sox need to spend significantly more money and take a chance on Holliday adjusting to the AL and to Boston.

Out of those five, I think the highest priority for this offseason should be Bay. I don't want him to hit free agency; he's a proven bat, he adjusted well to playing in the AL East, and Fenway suits his swing. 3 years at $12.5m would put him in line with Lowell and Ortiz and give you 4 years of Bay for $45m, or $11.25m per.

But could he be had for less? I get the feeling that he could. Bay's never seen a huge contract; he made $5.75m this season, $3.25m in '07, $750k in '06, $660k combined in '04 and '05. He also seems happy to be in Boston:


link

Extending Bay seems like an obvious choice to me, and I'd like to see it get done quickly.

Bay is a year away from free agency and his peers are making upwards of $14-18M a year. There is zero chance he is taking 4/45. None.

I would offer him 5/70 (same deal as Drew) considering he is making 7.5M this year (that would be replaced by the new deal). He would effectively net 4/63 from it. I'm not even sure 5/70 would be enough. Again, the guy is 1 year away from a huge payday.

I looked at TangoTiger's salary gadget (sorry, don't have the link handy) a while back and estimated that Bay would command $100mm for a 5-year deal as a free agent. Applying TT's methodology, you discount that by 25% for buying out a year of arbitration. So normally, we'd be looking at 5/75. Given the glut of LFs going into free agency this year and next, I think Bay might slide to 5/65, and would be a good signing at that price.

I don't see Bay taking less than 4 years under any circumstances. He can hit free agency after 2009 (his age 30 season) and sign a long-term deal then. Signing a 3-year deal now would push out his FA eligibility until after his age-32 season (age 33, if the deal included a club option). That's simply not in Bay's best interest.

Edit: Among the team's younger players, I think Lester and Pedroia are the ones most likely to agree to long-term deals, for the reasons others have stated above.

Bay is only cheaper now. If they both hit the market at the same time (along with a glut of other LFers) then they are likely to drive each other's prices down.

By contrast Holliday projects to be not only a more productive hitter, but a better fielder as well. If people are responding to my posts in this thread I should make it clear that if Bay would sign a more favorable extension then I would be all for that, with the saved resources being used to augment another position. I'm just assuming that since he's close enough to a big payday he won't sign for enough of a discount that I wouldn't rather have the extra marginal wins that I think Holliday would provide.

And of course I think the whole "adjust to the AL and Boston" is pretty weak argument that sounds like it belongs on bad sports talk radio along with "intangibles." How much of a risk is it anyway?

First, I don't accept your premise that Bay is "only cheaper now." Given Holliday's impressive numbers (moreso out of context), his age (one year younger) and the possibility that Bay may accept a bit of a discount to stay in Boston (given his statements about liking the atmosphere, etc.), I think it is very likely that Bay could be had cheaper than Holliday.

Second, I remember reading how silly the "playing in Boston" argument was back when Theo was letting Cabrera walk and committing a bunch of money to Edgar Renteria, who appeared on paper to present a slight upgrade from OC. I silently accepted the argument then, even though it seemed unnecessary to take a chance on Renteria adjusting when OC was already tested and was a fit.

Now, off-the-field issues seem in hindsight to have made the discussion moot with respect to Cabrera in 2004. But once again, I don't see a slight upgrade in on-paper production worth taking any risk on Holliday. If Bay can be had even slightly cheaper, the Sox should make it happen and not look back. And this is all not even getting into the second layer of risk, i.e. what effect leaving Coors Field has on Holliday.

edit: I know I said I wasn't getting into that second layer of risk, but yikes: Holliday has a career slugging percentage that is 190 points lower away from home, and an OBP of .348 on the road (compared with .423 at Coors). This doesn't worry you at all? Even this season, his slugging percentage was 100 points lower on the road.

Jason Varitek would also love to stay in Boston and finish out his career. That doesn't mean he's going to sign a below market rate contract to do so. As I said, if Bay will take a discount, then by all means sign him. But if he won't then I think it behooves the Red Sox to spend the money on the better player.



Of course the flip side is that everyone said that JD Drew wouldn't be able to play in Boston. Renteria outplayed OC that year; perhaps OC just couldn't hack the tough Anaheim environment? Is there any difference between "can't play in Boston" and "might have a bad year in Boston?"

Honestly? When will the madness end? If this nonsense keeps up, you should be demoted to Private Coop. What relevance do his age 24 and 25 numbers (when he wasn't even a full time player) have on his projected offensive performance going forward? How about we look at the last 2-3 years instead of ancient history when he was still developing as a player.

Year Road OBP Home SLG Road SLG SLG Diff

2006 .333 .692 .485 .207
2007 .374 .722 .485 .237
2008 .405 .584 .486 .098

He's obviously inhuman at Coors, but he's far from a slouch on the road. And let's also remember that 27 out of his 81 road games are played in Petco, Dodger Stadium, and ATT Park. His steady improvement on the road, and tough environment in which those games are played is indicated by his road OPS+ pver the last three years of 116, 130, and 145 respectively. In retrospect, t was over the top to say that Bay can't hold Holliday's jock, but Holliday is an elite bat IMHO, with Bay a half tick below. If Holliday is going to cost you something ridiculous like 7/$130, then you try to see if you can lock Bay up along the lines of JD Drew money. But let's not kid ourselves into believing that Holliday is some sort of Bichettian product of Coors Field. That's a silly argument with no basis in reality.

Edit: I suck at posting stuff in tabular format.

Right. And if Jason Bay were a Boras client, I wouldn't expect him to give the Sox a discount, either. You can't throw Varitek out as a comparison and ignore that rather obvious and substantial difference.



No one is arguing that every single player is negatively affected by the environment here. But some are, and again, I don't see enough of a justification to take the chance that Holliday is one of them.



I agree with everything you say here. I guess my assumption is that Holliday is going to command a lot more money on the open market than Bay will demand from the Sox for an extension. That's where we part ways, I guess. I certainly would not compare Holliday to Dante Bichette. Holliday is a great slugger, I would love to see him play for the Sox, but I just think Bay will end up being the more efficient option.

Have you actually tried to figure out what the risk of this is, or are you just talking out of your ass?

To put it another way, what in Holliday's past performance or make up has given you any indication that he can't "play in Boston?" At least Renteria came with a warning from Tony LaRussa (although he neglected to publicly mention that there was a sub-clause about playing through a back injury all season).

At halftime of the Celtics game, Comcast Sports announced that Pedroia and the Sox are now in negotiations for an extension. WEEI as cited as the source, though I can't find anything pertinent on the web site yet.

Rob Bradford buried this particular item in his story posted today: Pedroia Is History in the Making.