Given a relatively weak free-agent class and a stagnant economy, the baseball world is unlikely to see any Teixeira- or Sabathia-sized blockbuster deals this winter. Nonetheless, the consensus regarding the current crop is that left fielders Matt Holliday and Jason Bay are the top two hitters available, and with four of the game’s six highest-payroll teams-the Yankees, Mets, Red Sox, and Angels-among those with vacancies in left or at designated hitter, it stands to reason that both will net tidy deals. What separates the two players?

On the hitting side, not a whole lot, particularly after adjusting for ballpark. Bay just turned 31 in September, and owns a career .305 EqA. With the Red Sox in 2009, he put up a .306 EqA while bopping 36 homers. Holliday will turn 30 on January 15, and he owns a career .307 EqA. He split 2009 between Oakland and St. Louis, finishing with a .318 EqA (.298 in Oakland, .347 in St. Louis) and hitting 24 homers. The major point of contrast is that Bay walks considerably more often, drawing an unintentional pass in 11.8 percent of his career plate appearances, compared to 8.2 percent for Holliday. It all comes out in the wash: Holliday owns a Clay Davenport-translated career line of .312/.384/.541, while Bay is at .285/.384/.540.

The two contrast more starkly when it comes to defense, but even so, getting a handle on the magnitude of the difference is difficult. There’s no magic bullet for defensive metrics, and multiple mirrors on multiple walls will yield multiple answers when asked who’s the fairest of them all. For this look, I’ve incorporated the Runs Saved portion of John Dewan’s observation-based Plus/Minus system (available at Bill James Online), Mitchel Lichtman’s Ultimate Zone Rating (available at FanGraphs), and the play-by-play version of our own Fielding Runs Above Average (available in our Baseball Prospectus annual, with similar numbers on our website). Here’s Holliday over the last three years-enough time to get the kind of sample size that many consider necessary to properly evaluate defense:

Year Team        +/-    UZR   FRAA  Average
2007 Rockies       2   14.2     6    7.4
2008 Rockies       5    9.1     4    6.0
2009 A's          11*   6.6     4    7.2*
2009 Cardinals          0.9    -1
Average            6   10.3    4.3   6.9
*: Combined total between two teams.

Depending upon the system (and how willing you are to pretend you know nothing about significant digits), Holliday rates from 4.3 to 10.3 runs above average per year. While the various individual metrics swing about three to six runs per year, the three-system average is surprisingly stable, around seven runs per year. Only in last year’s late-season stint with the Cardinals did Holliday rate below average in any of the metrics. Turning to Bay:

Year Team      +/-     UZR    FRAA  Average
2007 Pirates   -11    -11.5    -11   -11.2
2008 Pirates    -7*   -10.3    -16   -16.4*
2008 Red Sox           -8.0     -8
2009 Red Sox    -4    -13.0      0    -5.7
Average        -7.3   -14.3   -11.7  -11.1
*: Combined total between two teams.

Turn off the ugly! Bay has rated from 7.3 to 14.3 runs below average per year since 2007; only one of the nine full-season marks grades him at average. The year-to-year averages show a much wider swing than on Holliday, as Bay’s average improved by more than 10 runs from 2008 to 2009. Some of the variance may be due to the system’s difficulty in adjusting for Fenway Park’s 37-foot high Green Monster; many balls hit in play to left field are completely impossible to turn into outs. Even so, consider that Manny Ramirez, whom Bay replaced as Boston’s left fielder in August 2008 and for whom Plus/Minus’ “Manny Adjustment” is named, averaged -7.1 runs per year across the three metrics for the period. Prorated to the same number of games in the field as Bay to adjust for time at DH and under suspension, that bumps him to -9.4 runs per year. Which means simply that Jason Bay is a worse fielder than Manny Ramirez. More importantly, he’s a much worse fielder than Holliday, by a whopping 18 runs per year, which is nearly two wins. What does that mean regarding the current market?

Holliday has been the subject of more rumors than Bay, with the Yankees, Mets, Red Sox, Angels, and Cardinals all at least loosely connected to him via one report or another. The Yankees could presumably offer the most money, and Holliday would fit well in NuYankee Stadium’s larger-than-average left field given his above average speed. But after committing $423 million to three prime free agents last winter, the Yankees have indicated that they’re less likely to hunt big game this winter, and are more focused on retaining incumbent left fielder and World Series hero Johnny Damon on a short-term deal.

Were the Red Sox to swap Bay for Holliday in their lineup by signing the latter, they would get a bit younger and significantly better defensively, always worth something in the ultra-competitive AL East. The Mets, with their spacious Citi Field outfield, would also be a good fit given Holliday’s defensive skills, as they were particularly awful in left field (-6.3 runs according to UZR, -10 according to FRAA). With Jose Reyes, Carlos Beltran, and Johan Santana among those returning from significant injuries, they have a ton of question marks, and they may face payroll constraints. The Angels claim that John Lackey and Chone Figgins are at the top of their priority list, and that Holliday isn’t the object of their current focus; they’ve also got Juan Rivera under contract, and they retain some interest in free agent Vladimir Guerrero, clouding that picture.

As for the Cardinals, they’re in a different financial class, with a 2009 Opening Day payroll that was $25 million less than the Angels’, the next-lowest team here. Still, Holliday hit well for them, and St. Louis just hired Mark McGwire, who served as Holliday’s private instructor last winter, as their new hitting coach (which may explain Holliday’s early-season struggles, come to think of it). If the heavyweights don’t pony up the $100 million deal agent Scott Boras says his client seeks, a return to St. Louis certainly seems possible.

As for Bay, he’s a known commodity for the Red Sox, who appear interested in retaining him. That may not be a great thing when it comes to considering defense; not only was Bay’s glove work significantly below average, but so was that of center fielder Jacoby Ellsbury (-10 FRAA, -18.6 UZR, -8 Plus/Minus). The Sox would be better served opening their wallets for the plus fielding of Holliday, all else being equal. The Yankees’ interest in Bay is thought to be even more tepid than it is for Holliday. The Mets might have more interest if Bay comes in at a lower price tag than Holliday, but he would hardly upgrade their defense, and with Beltran in center field after a year lost to knee problems, that may not be smart money spent.

One potential fit for Bay is the Mariners, who have shed more than $43 million in salaries from their Opening Day 2009 payroll. Bay has Seattle connections; he lives there during the offseason, and has additional connections to the area, having attended Spokane’s Gonzaga University. The M’s also possess the game’s standout defensive center fielder in Franklin Gutierrez (+25 FRAA, +29.1 UZR, +24 Plus/Minus), so they could more likely withstand Bay’s defense. They could spot Bay at DH as well, an option that’s less likely with the Red Sox and impossible with a National League club. The recently re-signed Ken Griffey Jr., who spent just eight games in left last year, is not really an additional obstacle.

At a marginal value of $2 or $3 million per win, Bay is worth about $3.6-$5.4 million less per year than Holliday, assuming the two are equal as hitters. As the two players field offers over the coming weeks, it will be interesting to see whether their potential suitors see things similarly.

A version of this story originally appeared on ESPN Insider Insider.

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The thing I have never seen mentioned about Bay and the sox is the tact the papi is out of contract after 2010. My belief is that bay is a stopgap outfielder until the kids are ready then Bay can move to DH more pemanently.
I haven't seen it either. Heck, I'm a Red Sox fan, and I didn't know that Ortiz's contract is done after 2010. That upgrades my opinion of keeping Bay. I'm still not sold on Holliday given what he did during his turn in the AL.
The point about Ortiz is a valid one. I'm not sure how much stock should be put in Holliday's numbers in Oakland particularly as they pertain to Boston. The Coliseum is a favorable park for pitchers, as are Safeco and Angels Stadium. In the AL East, Fenway is obviously a fantastic hitters' park as is Camden Yards, and at the very least Yankee Stadium is a better hitters' park than those aforementioned AL West parks.
I was under the impression that Fenway dampens homers slightly, while increasing markedly the number of doubles (and, potentially, triples, given the weird RF and huge CF peak. I also can't get Holliday's pre-2009 road numbers out of my head. The last annual refers to them as "roughly Shane Victorino". And then he went on to hit much like I'd expect a road-version of Holliday to hit (in his AL tenure). Basically I'm afraid he's going to be another Penny/Smoltz, where he isn't great except with the NL team. But I would guess EqA and Clay's translations show the real difference (which is to say, not much, offensively).
The thing that bothers me most about Holliday is that he's a Boras client, which means there's a good chance that negotiations will drag out until long after all the other free agent options have been signed and anyone available worth trading for has already been traded.