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Fun With Steve Phillips, GM Extraordinaire

Early this week Steve Phillips opened his mouth and forced me to create a post surrounding his ludicrous statements. As a result of writing this post I looked through my archives to find the picture to the right, in the process of finding the picture I stumbled across this post surrounding Steve Phillips Red Sox offseason thoughts in 2007 which included a trade as baffling as the Oswalt for Strasburg trade. So just for fun, let's debate which thought by Steve Phillips was worse.

Trade 1, 2007 Offseason: Jacoby Ellsbury, Jon Lester & Clay Buchholz for Johan Santana

During the 2007 offseason the Red Sox were kings of the world having swept the Colorado Rockies 4-0 in the World Series, but Johan Santana was the best pitcher in baseball and the Twins quite obviously were looking to deal him. The Red Sox were amongst the whispered favorites so Steve Phillips master ESPN commentator was asked what he would do if he was Theo Epstein. This is when Steve Phillips lost his mind and said that he could see the Red Sox dealing Jacoby Ellsbury, Jon Lester and Clay Buchholz for Johan Santana.

At the Time: At the time we didn't know that Lester was going to emerge as one of the best pitchers in baseball but we did know this, he threw 5.2 shutout baseball in the World Series after beating cancer and his stuff in the process looked electric. We also knew that Jacoby Ellsbury was a heart throb in Boston and was their leadoff of the future having hit .438 in the World Series. Clay Buchholz was a 23 year old stud prospect who threw a no hitter in his first month of professional baseball.

At the time Johan Santana was still regarded as the best pitcher in baseball but was coming off his worst season as a Twin. There were concerns about his arm and he was about to command a huge extension as he only had 1 year remaining on his deal. But again Johan Santana was a proven commodity, in his prime, and was still really really good.

In Retrospect: In retrospect this trade would have been GOD AWFUL for the Red Sox. First off Jon Lester has been the equal to Johan Santana over the past 2 1/4 seasons. His stats are slightly inferior but he pitches in a much more difficult league and has not been injured in either season. Ellsbury has been a solid catalyst for the Red Sox in his first two full seasons and led the AL in steals both years. Buchholz did not live up to the hype in 08 but found his groove towards the tail end of 09 and has arguably been the Sox best pitcher in 2010.

And of course the biggest reason why this trade would have been a complete failure is money. Not only have the Three players been more valuable to the franchise than Johan Santana would have been, they also cost a hell of a lot less. Their combined salaries in 08, 09, and 2010 is under 9 million. Meanwhile Johan Santana is going to make $60 million dollars from 08-10.

Trade 2, 2010 Midseason: Roy Oswalt for Stephen Strasburg

I could go into this trade again in full detail but it was already done on Tuesday, so let's just sum it up. Stephen Strasburg is the biggest pitching prospect ever. Ever. In the history of baseball there has never been more hype surrounding a pitcher than Stephen Strasburg. Meanwhile Roy Oswalt is 32, making way more money, and has not lived up to his standards in either of the past two seasons. Granted he looks like he might be having a bounce back year, but you can't give up the best prospect in the game for a player who's past his prime and you will owe at minmum 33$ million dollars over the next two seasons whereas Strasburg is just owed 15$ million over the next 4 seasons.

The Verdict

Both trades would be horrendous and it's almost impossible to decide which one would be more moronic, but I'm going to say the Red Sox - Twins deal would have been the worse move. The Red Sox would have given up three premium players that are all essential components of their franchise for now and for the foreseeable future and were on the books for 1/8th the amount Santana has been paid. Neither Lester, Buchholz, or Ellsbury are what Strasburg is supposed to become but the combination of the three is certainly greater.

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