You can’t judge a trade or non-trade immediately, but 4 years later gives you a pretty fair reading. Prior to the 2008 season, the Minnesota Twins were actively shopping Johan Santana who was entering into the final year of his contract before becoming a free agent. The Red Sox and Yankees were in hot pursuit competing with each other for Santana’s services. Both had offered valuable packages of top prospects to land Santana. Lester and Ellsbury had been offered to the Twins in separate packages.

After watching Lester come up small in a big game against the Rays while Santana threw a complete game shutout the following afternoon, I thought about what might have been and what would be yet to come if Theo had pulled the trigger on a trade for Santana.

 

They say that sometimes your best deals are the ones that you don’t make. Since the end of the 2010 season many Red Sox fans have assumed that we were lucky that the Red Sox front office had pulled its offers off the table and let the Mets land Santana. This seemed to be a safe and certain conclusion since Santana had shoulder surgery and missed the entire 2011 season while Ellsbury had become a star and Lester was our number 1 pitcher. People have been saying: “where would we be if we traded Lester and Ellsbury for Johan.”

That’s an interesting statement. First of all, we haven’t won anything with Ellsbury and Lester since the Johan non-trade. The Red Sox have missed the playoffs in 2010 and 2011 and they haven’t won a single playoff game in 3 seasons. It’s also an interesting statement since there was never a package on the table that included both Lester and Ellsbury. There was a package that included Ellsbury and Buch or Masterson.

So, where would the Sox be if Theo had pulled the trigger and traded Lester or Ellsbury and Buchholz? Well, we might have won another championship as Johan was still Johan in 2008. I realize that Lester had a very good 2008 season, which some would argue was comparable to Johan’s 2008. Lester was pretty good in 2008, but Johan Santana is a different cut of beef altogether—a special pitcher.

If the Twins had opted for the Ellsbury/Buchholz package, we would have had both Lester and Johan in the rotation in 2008 and beyond. Wow, that would be top shelf. Also Buchholz was a terrible 2 wins and 9 losses in 2008, and the Red Sox lost the division to Tampa by only 2 games. It’s reasonable to think that there would be another championship banner hanging in Fenway for 2008 if Theo had taken the plunge.

People say we dodged a bullet, because Johan has been injured and missed an entire season. Yes, he has been injured, and he did miss the entire 2011 season. What would that have done to the Red Sox? Wait a minute. The Sox missed the playoffs in 2011 experiencing an historic September collapse. Could it have been any worse? I don’t think so. Oh, and didn’t Buchholz also miss most of the 2011 season?

Yes, so where would the Sox be? Johan is back almost to being Johan again. He is pitching very well and striking out more than a batter per inning and on Saturday afternoon he threw a complete game 4 hit shutout. Buchholz, on the other hand, has been doing his best John Lackey imitation with a 7.84 ERA after 9 starts.

Okay, okay, but where would we be without Ellsbury? Who would play centerfield? Look at the breakout season he had in 2011. While Ellsbury did have a breakout season finishing second in the 2011 MVP voting, his great season didn’t prevent the most embarrassing collapse in Red Sox history.

It reminds me of what Branch Rickey told Ralph Kiner when Kiner was asking for a raise because he had led the league in HRs. My recollection of Kiner’s story is that Rickey told Kiner: “We finished last with you last season. I am sure that we can finish last without you.” Also, in the five seasons since Johan has been traded, Ellsbury has missed most of 2 seasons with injuries, while Johan has missed only one full season.

We’re into the fifth season since the Red Sox didn’t get Johan Santana. When considering whether it was a good or bad non-trade, it’s just not as clear as most people think.

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