1. Moving on from the A-Rod fiasco: After months of negotiating with the Texas Rangers during the offseason of 2003, Theo had a deal in place to trade Manny Ramirez AND Jon Lester to Texas for A-Rod.
But, after contract negotiations failed, the deal collapsed and A-Rod eventually went to the hated rival New York Yankees. Epstein cleaned up the mess and moved on.
2. Signing Mike Timlin: Before the 2003 season, Epstein wanted to go with a 'bullpen-by-committee'. He went out and signed Timlin along with Chad Fox, Brandon Lyon and Bobby Howry.
This experiment failed fast but Theo saw that Timlin was better suited to be a set-up man. Timlin was effective and helped the Red Sox to the 2004 and 2007 World Series titles.
3. Henri Stanley to the Los Angeles Dodgers for Dave Roberts: While the hype and hoop-la was focused on the trade of Boston icon, Nomar Garciaparra, a little unknown trade was conducted by Epstein.
In getting Roberts, Epstein solidfied a weak bench. Roberts, known for his incredible speed, was added for outfield depth and pinch running.
His running was crucial in Game Four as he stole second base off Mariano Rivera and eventually scored on Bill Mueller's single in the bottom of the ninth.
Roberts steal of second was voted the Boston Red Sox greatest play. That beat out Carlton Fisk's Game Six home run in the 1975 World Series.
4. Signing Hideki Okajima: An afterthought with the Daisuke Matsuzaka signing, Okajima has pitched brilliantly from the bullpen. He helped the Sox in 2007 as a backup closer for Papelbon and be the eigth inning set-up man for Boston. He has a 2.46 ERA since coming over from Japan.