Then why didn't Duke win with them? He swindled the Expos for Pedro, signed Nomar, gave Manny a ridiculous contract, traded for Lowe and Tek, and signed Damon. But he absolutely raped the farm system doing so. In turn, towards the end of his tenure, the Sox didn't have the prospects needed to have to make deals for the parts they lacked. Look at some of the teams that Boston fielded towards the late nineties and early 00s. Outside of Nomar, Manny, and Pedro, there wasn't much there. One could argue that Duquette wasted the best pitching years any one pitcher has ever had because he couldn't build the parts around Pedro to deliver a championship. Theo was able to. He was the one who brought in Ortiz, Schilling, and Foulke. Without those acquisitions, we're waiting on year 88. He had the balls to trade Nomar. Duquette did some great things as Sox GM. But he always fell just short.
Again, it comes down to the fact that Theo has made a committment to grow from within and become more financially responsible. Contending is easier when you don't have to rely on the free agent market as much. You can depend on your own resources, rather than catering to the whims of your competitors.