Originally posted on Fangraphs  |  Last updated 5/25/12

Roy Oswalt is getting closer to signing a contract, and while his reported preference is to pitch for one of the Rangers, Cardinals or Braves, the surprising first-place Orioles are quickly emerging as a dark horse candidate for his services. The Orioles may have lost a recent waiver claim to the Rangers based on their better record — which is still strange to type — but an aggressive pursuit of Oswalt, with a relatively lofty salary for three months, may pry him away from the Rangers, the current favorites in his sweepstakes.

The Orioles have been diligent in their pursuit to date, with Dan Duquette avoiding the topic or speaking in generalities when Oswalt is mentioned. Though he may not want to reveal his hand, the club has to have interest in Oswalt on some level.

Pitching is one of their biggest needs — despite relatively strong performance early on — and he is the perfect type of pitcher for the Orioles to pursue: he won’t cost a ton for half of a season, won’t require a commitment beyond this season, and is frankly better than some currently staffed rotation members.

Oswalt would help the Orioles as, at the very least, a better fifth starter than Tommy Hunter. Were he to achieve his pro-rated Fans Projection of ~1.5 WAR from July to September, he also figures to prove as valuable as anyone else in the rotation. The Orioles starting core has produced 3.5 WAR to date, which ranks 6th in the American League.

However, it’s tough to expect Jason Hammel to continue pitching at this high of a level; there are always injury concerns about younger pitchers like Brian Matusz and Jake Arrieta; and not enough is known about Wei-Yin Chen‘s true talent level with respect to how he’ll fare from here on out. Suffice to say, standing pat is foolish for the Orioles, but so is upgrading this team by surrendering prospects. By signing Oswalt, the Orioles would bring in a solid, veteran pitcher without having to part with any member of a top-heavy farm system still undergoing renovations.

Though 2011 was the worst season of Oswalt’s career, he still pitched effectively and produced 2.5 WAR over 24 games (23 starts). His peripherals were solid, with a below-Oswalt 16% strikeout rate, a 5.5% walk rate that matched his career mark, and a 45% groundball rate in line with seasons past. He pitched well, but wasn’t an ace, and somewhat declining performance coupled with injury concerns and his limited list of desired teams kept him from signing a player-friendly contract this offseason. Now, as the season has played out for almost two months, Oswalt has far more leverage in contract negotiations and it’s becoming clear that even the watered down version of himself from last year could prove very valuable, especially to a team like the Orioles.

From Oswalt’s standpoint, however, the Orioles aren’t an ideal fit. Despite starting the season off at 28-17, they are still regarded as a quasi-contender, if a contender at all. The Orioles aren’t strangers to hot starts, and as Rany Jazayerli recently noted, 2012 may play out similarly to several other seasons this millennium in which they looked strong early on and faded down the stretch. From Jazayerli’s piece at Grantland:

The 2005 Orioles won 17 of their first 24 games, and on the morning of May 27 they were 30-16 and leading the AL East by 4.5 games. They were 42-28 on June 22 and still led the division by two games. They were knocked out of first place three days later, and eventually lost 60 of their last 92 games to finish 74-88.

While the Orioles have played well through 8-14 games in various seasons since 2000, the 2005 campaign described above is most similar to their current run. At 28-17, they hold a slim one game lead over the Rays for first place, but have played solid baseball for far more than a week or two. Despite their good play through May, there are reasons to expect the same story to unfold.

The Orioles bullpen has a collective .246 BABIP and 83% strand rate. Their -5 UZR ranks towards the bottom of the league. Their lineup has the highest strikeout rate in the league and a bottom-half walk rate. Based on their runs scored and allowed, they are closer to a 24-21 team, which, while decent, would put the team in third place.

For Oswalt, the Rangers, Cardinals and Braves all represent better options as their playoff odds are greater. Those three teams are also more likely to play this way two months from now, and Oswalt probably wouldn’t want to spend what could amount to his last major league season playing for a 79-83 team that looked great through 45-50 games.

Oswalt is also unlikely to sign with a team that could fade down the stretch and look to trade him, as he has leverage now and can simply sign with someone less likely to experience that fade.

This isn’t to say the Orioles will absolutely finish the season under .500 and out of the playoff picture. It’s entirely possible this is just one of those years where they defy expectations and win a very tough division. But they’ll need guys like Oswalt to stave off regression while keeping the farm system in tact.

In that regard, this situation, like most others that have come before it, takes on a Catch-22 feel. The quasi-contender needs the player to maintain that status or increase their playoff odds, but the player prefers to go somewhere that has a better shot at making the playoffs without the effects of his production.

There is plenty of incentive for the Orioles to aggressively pursue Oswalt. They are by no means the favorite to land him, but with the Rangers looking more and more like the favorites each day, it’s time for the front office to make a concerted effort to bring him in. It’s time to throw generalities and vague niceties out of the window and negotiate.

The Orioles season doesn’t hinge on his signing, either way, but there is such little risk here for the Orioles — even if he gets hurt after one start and misses the season — that pursuing him is a no-brainer.

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