@iortiz - The problem with Kuroda was that he had a no trade clause that he said he would not waive to go to Boston. The problem with Jimenez was that the Guardians gave the Rox more than the Red Sox had to offer if they wanted to.
Bedard, Harden, Fister, Dempster were the only ones really available, and at the time, Lackey was throwing well enough, Bedard was going to slide into the 3rd slot, and Wake was going to take over as the 5th man. They were wanting to get both Harden AND Bedard, but Oakland was demanding too much for Harden with a bad physical. The Tigers overpaid for Fister, although he's been brilliant since the ASB, and you can make an argument for him. Still, though, I think the Tigers offered more for Fister than the Sox would have been comfortable giving up for a middle-of-the-rotation starter. The reason the Tigers gave up so much was because they had Verlander - Scherzer as their 1-2 punch. Now, with Fister, they can go toe to toe with anyone 1-2, which makes them awfully dangerous.
Basically, other teams were more desperate for SP than the Red Sox at the deadline. The deal they made was a solid deal while not mortgaging the future.
Trust me, in a couple years when Jimenez is posting 4+ ERA's, and guys like Will Middlebrooks, Jose Iglesias, and Anthony Ranaudo are the new Dustin Pedroia's and Clay Buchholz's of the team, you'll be thrilled we didn't pull the trigger. It was just a couple years ago that the best move Theo made in the offseason was not pulling the trigger on Johan Santana, which would have cost Lester + Ellsbury +1 IIRC.