Tyler, thanks for a great article.

A quibble: I really think that the 2009 deadline trades are going to be considered among the worst with time. V-Mart wasn’t enough to put the Red Sox over the top in 2009 or even enough to get them to the playoffs in 2010. While it’s probably not significant at the 99% confidence level, his game calling in Boston was bad, much worse than Varitek’s. Yes, he hit; he didn’t play well enough to win.

In return, the Indians picked up Justin Masterson at a much lower salary, and he rapidly became their best starting pitcher. Furthermore, LaRoche did far better than Kotchman did through the late summer and autumn.

Theo gave up a potential winning season in 2009 by creating a Wild Card winning team not constructed well enough to win a single playoff game. He lost a capable front-line MLB starter to get to the ALDS and lose, as well as picking up millions of dollars of salary liability. That’s a bad trading deadline.

Wow, I didn’t realize how poor Theo did at making trades until I saw this article. Very surprising/enlightening. He still has put together a great farm system, but he seems to get the short end on most trades.

It’s funny how hind sight governs these so much. Where would #1 rank had the Yankees done what every other team in MLB history had done with a 3-0 lead? Conversely how would the 2003 rank had the manager gone to his bullpen when everyone thought he should have?
I remember some of these deals and at the time, Suppan, V-Mart and Gagne were the best deadline deals of those years and coveted players by most contenders so at the time GM of the year potential moves.
To counter argue the Sanchez deal, would we have Pedroia if he was not traded? I’m happier they kept the position open for Pedroia to fill it rather then making him expendable.

Not a bad article, but a glaring omission: Gagne was just as much about getting a compensation pick free-agent to replace players who would never become part of the Sox lineup, and were out of options/roster spots. This allowed them to pick Bryan Price.

You missed also that Price was then packaged with Masterson/Hagadone for Martinez… a good addition for the Sox, who produced, moved on, and netted draft picks, which were then used for highly-touted Matt Barnes, and promising lefty Henry Owens.

I’d do the Gagne trade for that. The only bad part is that he had to clog up a roster spot to get that compensation, but Murphy and Gabbard were likely both gone soon anyway, because there wasn’t room for them.

Yes but Brandon Lyon was part of the Curt Schilling trade!!

Masterson trade was terrible,until Detroit signed Vmart.You don’t trade good starters for a dh under contract for 1.5 yrs.Thank you Tigers,i love Barnes,might be better than Justin who knows.I never thought Vmart could catch and the more i watch the more obvious it was.

Never understood the deal for Gagne. It was terrible. Love the trade when they got rid of Garciaparra. He had more than worn out his welcome with me and I think that trade was what won the championship for us. Manny had become a cancer and the trade to get rid of him was a good one. The Saltalamacchia trade wound up a good one for us. I enjoyed V Mart more than some but did hate to see Masterson go

We need a reliable pitcher. I think we have enough offense to make it to the championship, but not enough pitching. Losing Dice K was a blessing as far as I was concerned. I hated to watch him pitch. Also, Theo got blamed for that acquisition and I don’t think it was him but the other guy that had authority to make such an acquisition.

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