Maybe the island(or smokey or jacob or mystery dude) won't let Widmore die just like it wouldn't let Michael die until Widmore has performed some act. Maybe thats why Ben couldnt kill him.....he may have tried to or had someone else try to and figured this out.
If memory serves, Christian appeared and told Michael that the island was done with him right before the freighter blew up. Perhaps Widmore will go out in a similar fashion in season 6.
The island may also be responsible for Desmond's bulletproof shopping bag.....or maybe, like most guys, Desmond doesn't know how to buy groceries and he bought some stale rock hard bread and a bunch of frozen microwaveable meals.