Well, as slasher said, both built the farm at the same time. Why is that so unimportant?
And neither left the Sox in the position they are in now, with payroll limitations and no help on the horizon in the form of minimum wage players with potential to contribute.
Even you yourself said Bloom has a "monumental task" in front of him to be competitive while staying under the limit. Why is that?
Spending it an easy way to succeed, but there is a clear an obvious downside, which comes when the expensive players inevitably are no longer the stars that were paid for. At that point, having the farm system helps mitigate that damage, by getting contributing players who don't require $10mill paychecks. Right now the Sox have the expensive contracts whose contributions appear to be declining, but nearly nothing in the way of minimum wage help to offset things. This could be a big problem. And this is where Dombrowski failed. It's like someone who takes their retirement savings to fund a trip to Vegas. Sure the Vegas trip/World Series title were fun, but once they are over, then what?