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Roy Oswalt - Scott Ableman (Flickr)

Oswalt In The Future?

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Both Peter Gammons and MLB.com have mentioned the plausibility the Astros could fall far enough out of contention by late June and into the trade deadline that their ace, Roy Oswalt, could be dealt. While the rumor didn’t seem to have much steam (often times Gammons exaggerates or even straight up makes things up when it comes to trade rumors), the fact the Red Sox have inquired about Oswalt’s services in the past gave me the idea Theo may have interest. Today, the Astros beat writer for the Houston Chronicle outlined the situation, and thought the Red Sox could be a possible destination:

I know Oswalt better than any player on that club. That’s not to say I know him tremendously because you never really, really know the players. But I’d put my working relationship with this guy against anybody in America.

Believe what you want, but I’ll tell you there are three teams he’ll accept a trade to, and those teams aren’t in New York. They aren’t the Yankees. They aren’t the Mets.

They are the St. Louis Cardinals, Atlanta Braves and Boston Red Sox.

From a biased standpoint, Oswalt has always been one of my favorite pitchers. His repertoire, while declining slightly, still possesses a dynamite fastball in the mid 90s with a hard snapping curve in the 80s and a slow, looping hook in the 70s. On occasion, Oswalt mixes in a slider and changeup, but the fastball-curveball combo along with precise control made him the pitcher that finished in the top-five in Cy Young voting five separate times. He works extremely quickly and has compiled over 1440 IP in his career with 1192 K and a 3.13 ERA. Oswalt has been the ace of the Astros for a long time now.

This year, Oswalt has fallen upon a rough start, one very unfamiliar to the Astros hurler. In just 30 innings, Oswalt has surrendered 41 hits, seven homers, six walks and 22 strikeouts while compiling a 6.00 ERA, 1.57 WHIP and 68 ERA+. In 2007, Oswalt finished with a 3.18 ERA, a 1.33 WHIP and a 138 ERA+. Surely, Oswalt will trend upwards this season. This may be the opportunity for Epstein to buy low.

Oswalt will obviously remain an Astro for the time being. Their record has yet to reach pitiful levels, but the emergence of the Cubs, Brewers and Cardinals as the clear cream of the crop in the NL Central leads me to believe the pitching-thin Astros are in for a free fall sooner than later. If Oswalt is on the trading block to Atlanta or Boston (I’m temporarily disqualifying St. Louis because GM’s are scared to trade within their division), should Theo pursue?

The negatives with Oswalt are as follows: 1) his K/9 has declined every year since 2004 and he is now 31 years old (7.82 career high in 2004 and 6.54 in 2007), meaning his once electric stuff is finding many more bats, 2) his BAA is also increasing from a career high .246 in 2003 to .265 in 2007, with every year in between pushing the number higher, 3) his mileage is high at over 1443 IP at 31 years old, 4) Oswalt surrendered 14 homers in 212 IP last year while in 2008 he has already surrendered seven.

While Oswalt may have already survived the worst stretch of this season, there is concern here. His trends show a severe decline and moving to the AL with more patient and powerful lineups will only hurt the cause. He also possesses four years remaining on a $60 million contract extension, and in the event of a deal, may ask for the deal to be bumped slightly higher.

If Astros GM Ed Wade finally reaches the conclusion his current concoction of a team cannot possibly win over the short or long term, he may realize Oswalt could net him the best group of prospects. Oswalt is still a phenomenal arm and his 60/40 GB/FB could translate well in the American League even with the upgrade in overall offense. He’s been a top five arm in the NL for five years now.

The positives are not only in the statistics (face it, the guy put up a WARP3 over 9 just two years ago and even reached 8.0 last year, his stuff is still there watching a few of his starts) but in the contract, which could be considered a bargain in today’s market. How much would Oswalt receive as a free agent right now? Somewhere in the range of six years and $90 million, correct? The 4/60 doesn’t sound all that bad, right? Oswalt will make $14 million in 2009, well worth a 3.75 ERA and 200+ IP he could very well accumulate.

The price: Could a combination of Jon Lester (thrive in a new environment? I’m not giving up on the kid, but there is some chance he will not pan out), Michael Bowden (#2 starter ceiling) and Jed Lowrie (face it, he’s blocked, and his value is climbing steadily) get the deal done? All three of those players have the potential to contribute very positively at the big league level, and if anyone convinces Wade he needs to rebuild, this may be where to start. Thus, the debate begins: Would you deal this kind of young talent for the ability to add Oswalt to a Beckett-Matsuzaka-Schilling playoff rotation with Buchholz ready?

Roy Oswalt may be a name floated around as the season progresses, and it makes sense for the Red Sox to, at the very least, take a flier.

9 Responses to “Oswalt In The Future?”

  1. Sam says:

    April 26th, 2008 at 2:13 am

    I was going to bring this up myself when I heard that from Gammons … while I don’t see it happening … in fact, it’s highly unlikely IMO … I’ve always liked Oswalt and they way he pitches … I dunno about health risks but he’d be a very good consistently competitive veteran pitcher … almost a Curt Schilling without the mouth … I’m not too sure on the package it would take to get him … but if the Stros would take Lester/Bowden/Lowrie (or maybe Moss?) I think you certainly have to think about it

  2. TALL THRILL says:

    April 26th, 2008 at 3:50 am

    I think we all agree that this trade isn’t going to happen anytime soon, but if we can acquire Roy Oswalt at the deadline, I am all for it. I even voted in the Lowrie poll question with a trade like this in mind.
    It will start with Lester and Lowrie, but honestly, I think it will take 5 prospects ala Santana and Bedard (or at least 4). I would love it if we can keep Bowden and Masterson.

  3. Troy says:

    April 26th, 2008 at 9:22 am

    Off topic. Heidi Watney will replace Tina C on Nesn.
    She is Hot but can she pitch in the Bullpen.

  4. Gerry says:

    April 26th, 2008 at 11:17 am

    Love to have Oswalt but, under such terms, he is not our guy. A younger, more successful, AL acclimated Santana would have been a better and surer deal for Lester, Lowrie, Bowden, Moss/Crisp and we didn’t pull the trigger then.

    In terms of trades, Theo can un-block Lowrie right now, as Julio’s #’s may never be better. Jed hits and fields better. We saw what Masterson can do at Fenway, and Bowden is in that league. Freeing Moss might be a good thing, as HE is blocked, and would start on most teams with +Murphy results.

    I am content for our top-rotation-in-waiting, of Colon, Schill, Becket, Daisuke, Lester, Buckholz, Masterson, Bowden to turn the corner.

  5. TALL THRILL says:

    April 26th, 2008 at 12:41 pm

    Gerry, Oswalt is less then 2 years older than Santana so I don’t like that argument. The numbers are similar, it is ALMOST debatable whose has had a “more successful” career to this point. I’m not going to argue that, but I thought I would point out that Santana’s career league era+ is 141, Oswalt’s is 140.
    The big difference (besides name) is salary.
    Oswalt
    08:$13M, 09:$14M, 10:$15M, 11:$16M, 12:$16M club option ($2M buyout)
    Santana
    08:$19M, 09:$20M, 10:$21M, 11:$22.5M, 12:$24M, 13:$25.5M, 14:$25M club option ($5.5M buyout)

    So you defiantly can’t use the age argument. With both contracts you would be locked in until after their age 34 season.

  6. Gerry says:

    April 26th, 2008 at 3:31 pm

    Good points. The struggles of the rotation, from Becket through Buchholz, and the Pen from MDC through Tavares, has created a certain nostalgia for the Santana deal. Did we blow it?

    As you demonstrate, one of the arguments against that deal ($$$) is less of a factor for Oswalt, about 30% less for equal talent, which is very tempting.

    The other argument against the Santana deal was betting the farm. Because of this farm system, the Sox are in first place in the league and in categories like BA and runs scored. Youk, Pedroia, Ellsbury, Lowrie, Papelbon, and a resurgent Coco, JD and Julio against whom they compete, have shined (shone?) during the long opening month of a mind and body numbing road trip against division leaders, injuries to a dozen players, a flu epidemic, and early struggles by top guns Manny & Papi.

    During this time Buckholz, Lester, Hansen, MDC, Masterson, Pauley, Ellsbury, Lowrie, Thurston showed what they can become with time, as the season stabilizes and progresses.

    I like Oswalt and Santana, even better than Harden and Haren. I really like hanging onto the “kids” and letting them develop . . . specifically this particular trade bait of Lester, Lowrie, Masterson, Bowden.

  7. Lisa Gray says:

    April 27th, 2008 at 10:16 am

    you left out the most important sentence of Jose Ortiz’ (the Astros beat reporter’s) paragraph:

    Oswalt would demand a Santana-like re-writing of his contract to any team who wanted to trade for him.

    translation: he does NOT want to leave houston

  8. Sunday night reading…delaying the inevitable | umpbump.com says:

    April 27th, 2008 at 7:31 pm

    […] MORNING! RUUUNNN!!! Here’s a few links to lull you back into a false sense of security: Fire Brand of the American League on the Roy Oswalt-to-Boston-at-the-deadline […]

  9. CaliGuy says:

    April 30th, 2008 at 10:27 pm

    Boston sucks. He’s not going there. Wake up you dumb asses.

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