Theo’s best free agent signing: Tito.

World Series titles: Scheueholz: 2 Epstein: 2

No, I’m not ready to say Epstein has had a better career, but give him time. He’s working the prospects the way Schuerholz did. And that fruit is starting to grow.

Look at the two World Series rosters and tell me Theo doesn’t build a roster well enough. Were there 5 holdovers? And weren’t those all guys Theo brought in? Look at the farm system’s improvement. They are nowhere near as dependent on signing big money “sure thing” free agents. Taking a gamble on injured guys is not a bad way to keep a roster spot warm or add another veteran to the clubhouse. It’s always a short term commitment and it’s usually low money.

Sure we can dissect every move Theo makes--especially when we don’t judge them relative to all the moves made by other GMs.

Since Theo's been GM for six full seasons, let's break things down. From 91-96, the team averaged 82 wins and made the playoffs once. (94 and 95 record adjusted to 162 games to compensate for strike) In the six years prior to Theo taking over (97-02), the Sox averaged 87 wins and made the playoffs twice. The following six years (03-08) they averaged 94 wins a year, made the playoffs four times and won two world series.

It’s funny the demand is something so close to perfection in a sport where the famous saying is that you’re an all time great if you fail in 7 of 10 trips to the plate. Two World Series titles, four trips to the ALCS and currently holding the fifth best record in ALL of baseball. But yeah, he really blew it taking a chance singing that future Hall of Famer to fill the #5 slot in the rotation for the middle third of the season!

PS—Whether Theo did the deal or not, no way I’d reverse the Hanely Ramirez deal, much less call it a disaster. Beckett and Lowell were significant players on a World Series winner.