To further illustrate this for Randy, here are the top 10 players in terms of salary for the Sox this year:
Gonzalez, Adrian $21,857,143
Crawford, Carl $20,357,143
Beckett, Josh $17,000,000
Lackey, John $15,950,000
Ortiz, David $14,575,000
Matsuzaka, Daisuke $10,333,333
Pedroia, Dustin $8,250,000
Ellsbury, Jacoby $8,050,000
Lester, Jon $7,625,000
Bailey, Andrew $3,900,000
Of those 10 players 4 have underperformed expectations entering this year (Beckett, Lester, Pedroia and Gonzalez) and 5 have missed over half the season (Crawford, Lackey, Matsuzaka, Ellsbury, and Bailey). Add in another $12.5 million of ineffectiveness and injury from Youk before he was traded to clear room for Middlebrooks and that's your recipe for a $175 million payroll and a sub-.500 team. And now that Ortiz has missed the majority of a month of play himself he may need to be added into the "not getting their money's worth" list as well.
The Sox would have needed Harry freakin Potter as GM to have been able to fix that mess.