I'm not sure your caveat, "not the broken down guys," is reasonable. Thus $22M on Story, $18M on Giolito, and $17M on Sale--all of them on the Sox payroll and none of them playing for the Sox--is not that unusual.
My view is much simpler. Players with big salaries are always a gamble because those big bucks are always guaranteed, sometimes for 10 or more seasons.
As I've said too many times, the Sox had the biggest payroll in MLB in 2019, and it wasn't going to be nearly enough to keep Mookie from going to the Dodgers and to replace Price and Sale while also paying their salaries.