This week, Neil was sacked by Stoke following a harrowing run of form that sees them sitting 19th in the Championship standings.
The 42-year-old left Sunderland to join Stoke last year in an acrimonious manner and his successor Tony Mowbray carried the Black Cats to the Championship playoff spots.
Mowbray has also been sacked but more than a year on, Neil is now jobless again and Bennett believes he should ask himself why he left a club where he was doing well.
He insisted that Neil is a cautionary tale of managers who feel more money to spend will get them success as it also adds more pressure to reach the promised land.
Bennett said on the BBC’s Total Sport Sunderland podcast: “Maybe ask the question, why did he leave?
“Is money everything? He was at a club doing well.
“It doesn’t work [that way], money doesn’t buy you success. It helps but it is not guaranteed to get you success.
“Maybe, it adds pressure.”
Mowbray is also one of the names Stoke are considering as a potential replacement for Neil.