Talkin Sox with Dan

Where baseball fans gather for commonsensical, opinionated Red Sox banter.

Oswalt May be Heading to St. Louis

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According to Mark Polishuk of, free agent pitcher Roy Oswalt will likely be toeing the rubber for the Cardinals next season. Jim Duquette of MLB Network Radio was the first to tweet the news last night. In his tweet, Duquette included that the Red Sox and Astros were still involved. Although nothing is official, I find it extremely hard to believe that Oswalt will be heading north to Boston or back his original team, the Astros. Just as TSWD wrote earlier this week, Oswalt, despite being in the latter half of his career and coming off of a year where he suffered from back issues, does reserve a fair amount of selectivity concerning the team he pitches for in 2012. St. Louis just makes the most sense.

A Mississippi native, Oswalt will be close to home if when the righty signs on with the 2011 World Champion Cardinals. Have the Cards lost their best player, a guy who will be talked about in the same breath as Stan Musial? Sure. Are they still an extremely good team that plays in a lackluster division? You bet. By joining the Cardinals, Oswalt will join a staff that includes Chris Carpenter (a TSWD favorite–guy’s a total gamer) and Jaime Garcia. Oh, and Adam Wainwright. Remember him? Yeah, he’s the guy that finished second in Cy Young Award voting in 2010 before undergoing Tommy John surgery last year. Oswalt will serve as a quality veteran presence in an already-quality pitching staff.

When analyzing Oswalt’s not-yet-official decision to join the Cardinals, it’s vital to take a look at the teams that were interested in his services. I’m not going to discuss the Astros’ involvement because I have no idea where their motivation is coming from–maybe sentimentality. Who knows? Two teams needed Oswalt (for argument’s sake, Oswalt’s name is interchangeable with ‘a relatively-quality starting pitcher’). The Red Sox and Tigers have question marks in their rotation. Oswalt would have filled a vacancy for both teams. According to Jon Heyman of, the one-year offer that Oswalt declined from the Tigers was worth close to $10MM. The offer from GM Ben Cherington and the Red Sox was likely closer to half of that figure. Clearly, money is not the motivation for Oswalt.

Location is the driving force.

St. Louis or Texas? The World Champs or Mike Maddux? Each destination is appealing to the 34 year old. Both teams possess deep staffs that really do not need Oswalt. In fact, each team would likely have to make some sort of move to accommodate Oswalt. Ken Rosenthal of offers a few creative explanations that would provoke them to pursue signing Oswalt. Texas would have likely had to move a guy like Alexi Ogando to the bullpen to create space for the right handed starter.

So where does this leave the Red Sox?

Edwin Jackson is still on the market. Sox fans need to come to the realization that the Red Sox are not going to overextend themselves for a starter. Jackson reportedly has more than one multi-year deal on the table. It is natural to believe that Scott Boras and his client would jump on three-year offer from a team like the Orioles. However, next year’s free agent class could prove to be more lucrative for Jackson. So, wouldn’t it make sense for Jackson to accept a one-year contract with the Red Sox? Not so fast.

Sure, Boras and Adrian Beltre were able to successfully parlay a productive 2010 campaign with the Red Sox into a long-term big money contract with the Rangers. He was a hitter playing in the AL East, however. Jackson could be conceivably pitching into the wind against an offensively potent division if he were to sign on with the Sox. Again, we run into the same problem we faced when we put ourselves in Oswalt’s position: Why, as a pitcher, come to AL East when the objective is to boost one’s value in an impending free agent market?

The Red Sox acquired some financial flexibility after the Marco Scutaro trade. That cannot be taken away. Time will tell whether the Sox choose to exercise that money now or at the trade deadline. No matter what, however, the success of the Scutaro deal is dependent upon Cherington’s ability to add a starting pitcher sometime between now and the beginning of August.

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2 thoughts on “Oswalt May be Heading to St. Louis

  1. I was all head over heels when Scutaro was traded because we all knew what Cherington had under his sleeve.. Oswalt was coming to town, Cherington had finally adressed his pitching problems and our rotation looked solid..

    He surprised us all with much needed help in Cody Ross, but then again people were wondering.. Where’s Oswalt? I mean the SOLE purpose of trading scutaro was to shed payroll and allow us to gain some money to offer him.. Sure we gained strength in the outfield which to me is perfect, because an opening day outfield of McDonald, Ellsburry and Sweeney puts me to tears.. But now the Oswalt is close to landing a deal with the Cardinals, and is reporting that Jackson has three year offers in the table, one has to wonder.. IF THE RED SOX ARE LEFT WITH THESE OPTIONS, AND THE ONLY WAY TO ADD A QUALITY PITCHERS IS VIA TRADE, THEN WHY IN THE WORLD DID WE TRADE SCUTARO?

    You might say we have the necessary backups in aviles/punto.. I had the chance to see Aviles play here in the Puerto Rico for winter ball since I leave here, but he is at best a backup.. He does have some offense in him, ill give you that.. but one has to wonder.. If the sole and primordial purpose of trading “scu scu scutaro” was to get oswalt or maybe jackson, and now were facing the possibility of getting neither, then what gives?

    Cherington already stated that the board has given him permission to surpass the luxuary tax, and not worry about it when it comes to adding depth to the team.. But noo we go AGAIN AND SIGN GARBAGE, IN THE FORM OF JOHN MAINE..


  2. Jorge–no reason to get mad at signing a guy like John Maine. He is just another arm to add to Pawtucket. Cherington is determined to be sure that the Red Sox are not in a position like they were last year where an injury or two forced them to use guys like Kyle Weiland.

    I agree that it is vital for the Sox to add a starting pitcher, but if the market determines that waiting to pursue a guy at the deadline is a better way to go, I’m okay with that.

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