It sneaked up on us a little bit (and by us, here, I mean me), but all of a sudden it’s very late in the offseason. It’s February 15th. The Athletics and Mariners have opened Spring Training already, sort of, and the rest of the teams’ pitchers and catchers report on Sunday. Major League Baseball will be played two weeks from Friday. Major League Baseball that counts will be played…well, that’s seven weeks from today. That’s still quite a ways off, really. But still, Spring Training! Soon!

And yet, as Matt Kory hilariously discussed yesterday, Roy Oswalt remains unemployed. That’s…odd.

Free agent signings always happen this late in the year, but they tend to be minor league deals, or near enough to it. A lot of players you probably wouldn’t expect to still have been playing in a season that late in time have signed contracts in mid-to-late February, typically to minor league deals: Matt LeCroy signed with the A’s on this date in 2008, Dave Hansen with the Cubs and Pat Mahomes with the Mets in 2005, Goose Gossage with the A’s in 1994 (they released him before opening day). The Mariners signed Ken Griffey, Jr. to his reunion/farewell tour contract three days ago Saturday; Bret Boone got a minor league deal with the Nationals on February 19th of 2008. Those—among many other, less interesting minor league sorts of names—are the type of signings you see at this point in the offseason.

It’s rare, or at least it seems rare, that we see a player like Oswalt languishing on the open market after Valentine’s Day. By “a player like Oswalt,” I mean: (1) who is of a quality to be a regular starter or starting pitcher for most teams; (2) who performed well in the prior season and has a history of performing well; (2) who isn’t old enough to give teams reason to fear his falling off a cliff; and (3) who doesn’t throw up any other warning flags (documented disciplinary problems, PED suspensions or the like). That’s Oswalt, as far as I can tell: he’s 34, he pitched very well in 2011, and while he had an injury that he once worried would end his career, he came back from that and showed no ill effects, with a 3.59 ERA in 69.2 innings. So how often do guys like that last this long?

What I’ve done is look back through Baseball-Reference’s leaguewide transactions pages for free agent signings between today’s date and opening day, from 1990 through 2011, looking for players comparable to Oswalt (note: we’ve got our own phenomenal tool for doing stuff like this and a lot more, but it’s new, and currently goes back only to 2009).

Using the general, largely subjective criteria laid out above, here’s what I have as the best player of each offseason (in terms of what we’d reasonably have expected of his next-season performance) to sign his free-agent contract on February 15 or later, assuming there was a projected average-or-better starter in the bunch:

2011: Vladimir Guerrero, Orioles, February 18.
2010: Johnny Damon, Tigers, February 22.
2009: Manny Ramirez, Dodgers, March 4.
2008: Kyle Lohse, Cardinals, March 13.
2007: Barry Bonds, Giants, February 15.
2006: Kevin Millwood, Rangers, February 22.
2005: None.
2004: Greg Maddux, Cubs, March 23 (agreed on February 18).
2003: Reggie Sanders, Pirates, March 10.
2002: None.
2001: Rickey Henderson, Padres, March 19.
2000: None.
1999: Ramon Martinez, Red Sox, March 11.
1998: None.
1997: Danny Tartabull, Phillies, February 25.
1996: None.
1995: None.
1994: Tony Fernandez, Reds, March 7.
1993: None.
1992: None.
1991: Willie Randolph, Brewers, April 2.
1990: None.

It’s an uninspiring list. It’s entirely possible that I’ve missed someone, but in nine of those twenty-two seasons, I was unable to find a single player signed after February 15 that the team signing him would have counted on to start that season. And in most of the years in which I did find one, there was only one who qualified; there was also Sammy Sosa in 2007, and Kenny Rogers in 2003, but that was just about it.

The names on this list break down into a few different categories:

1. The great but very old. Old in baseball terms, anyway. Both Bonds and Henderson, effective as they still were, were 42 (and Bonds probably violates one or two of those other criteria above, too). Guerrero was “just” 36, but had shown pretty serious signs of decline. Damon was also 36, and his excellent 2009 looked a lot like a trick of the New Yankee Stadium’s short porch. Randolph was also 36 and was a second baseman, which takes a lot out of a body. Ramirez was 37, and was demanding a ton of money (he ended up squeezing two years and $45 million out of the Dodgers). You can understand teams wanting to hold off a bit and think about it before they committed real money to the game’s senior citizens.

2. The injury prone. Randolph fits here, too, as did Bonds by 2007. Sanders, who joined his sixth team in six seasons (out of an eventual seven of seven), fits here. Martinez, Pedro’s big brother, had been extremely effective when healthy, but had managed just 15 starts the year before he signed. Tartabull hadn’t played in 140 games in a season in eight seasons when he signed his one-year, $2 million deal with Philadelphia in 1997…and then he fouled a ball off his foot in his third game as a Phillie and never played again. It makes sense that these players signed late; as effective as they could be when healthy, a team might want to exhaust its other options before it puts a lot of money into a player it perceives as a big gamble.

3. The last resorts. Millwood was coming off a 2005 in which he led the American League in ERA, but his FIP was nearly a run higher, and he’d put up a league ERA below league average in the two seasons before that. Lohse was, well, Lohse. These are the kinds of pitchers a team absolutely does want to wait on, and pick them up only when all the starters the team might have preferred have been taken.

That leaves two that don’t make as much sense: Tony Fernandez and Greg Maddux. Fernandez had performed brilliantly in 1993 for the eventual World Champion Blue Jays after being traded from the Yankees, hitting .306/.361/.442 and managing 2.7 WARP in just 94 games with Toronto. He was just entering his age 32 season, and he was widely considered a brilliant defensive shortstop. Yet he still didn’t have a job in early March, so he took a minor-league contract with the Reds—who, of course, already had Barry Larkin—to play third base. I haven’t been able to find any explanation for this. Tony deserved better.

The last, of course, is Greg Maddux. Maddux was entering his age-38 year, which qualifies him as “very old,” but he’d still been above average in 2003, was coming off of thirteen consecutive brilliant seasons before that. There was no reason to think he couldn’t keep being above average for another few years, which is what he did. Maddux is clearly the best (maybe the only, in this instance) comp for Oswalt. Oswalt, too, has been very good for quite a while (not nearly as good for nearly as long, obviously), and there’s no reason to believe he won’t continue being, at least, pretty good. By rights, both should have been snapped up by this point in the offseason.

Unfortunately, that theory falls apart, too. Much of it is explained here. The free agent market was flooded in 2004, so things happened a bit more slowly; there was never any doubt that Maddux would get paid, never any question that there was plenty of interest in his services. This year is different. There were a handful of good pitchers on the market, of which Oswalt was one, and some pitchers—lesser pitchers, in many cases—got snapped up while Oswalt sat there, seemingly kind of perplexed. Maybe Oswalt is actually more like Fernandez than Maddux, the one that fell through the cracks. Of course, some of this seems to be Oswalt’s doing, too, since he seems to be particular about where (and in what climate) he plays. I don’t think there’s anything in the last two-plus decades that really compares well to Oswalt’s situation at all.

So, what does that all actually mean for Oswalt? Well, nothing at all. It’s just an observation (albeit a long-winded one): it’s really, really unusual for a player of Oswalt’s age and abilities to have been left dangling out in the wind for this long. This kind of thing just doesn’t happen.

Thank you for reading

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"That’s Oswalt, as far as I can tell: he’s 34, he pitched very well in 2011... with a 3.59 ERA in 69.2 innings."

Correction, Oswalt pitched 139 innings in 2011. That's a significant difference.
Please look at the sentence again. I agree that that it would be wildly incorrect, if it read the way you type it here. But the part you cut out is pretty important.

That said, there was a minor typo there -- it should say 67.2 innings, not 69.2.
Does anyone (besides Oswalt) know for sure if he's received any offers at all? He clearly seems to be in decline, but he's still better than a lot of the mediocre guys that have been signed (e.g. Bruce Chen). Last year he sent out mixed messages about his future, leading people to think he might retire, and then of course there was the back problem. I think teams are just being really careful before committing.
I don't think anybody really knows, but I get the sense that he's turned some teams down before they've gotten to the table.
If Bruce Chen had a list of just a few teams he would pitch for and expected to be paid $10 million, he would not be signed, either.
The Tony Fernandez thing sounds like it might have been one of the cases of collusion. Was that one of the "collusion years"?
Isn't 1987 the only real "collusion year"? I don't think that's the case with 1994, anyway. Lots of free agents signed earlier, for more reasonable deals -- Will Clark, Eddie Murray, Rafael Palmeiro, etc.
Joe Crede Feb 21 2009

Does he count?
Eh...maybe. He wasn't playing full time anymore, really. Obviously not going on the list ahead of Manny.
Boston papers have been reporting that Oswalt "just needs to decide where he wants to pitch" - the implication being that he has offers on the table.

I think it's all him and not the clubs. Like Madson and Jackson, he may have had much higher hopes. Maybe he's just not in a rush to accept small money from a place he doesn't really want to play.
I don't think there is much of a mystery here. I think Oswalt's desires do not match up with those of the market.

Still, this is a nice piece about an odd situation.