Wilkins was assistant to Carlo Ancelotti until two years ago, when he was dismissed in a manner he describes as "crash, bang, wallop and off you go".
Ancelotti himself was sacked in May 2011, the season after Chelsea won the Premier League and FA Cup double, while Roberto Di Matteo was axed this season just six months after finally delivering the Champions League title Abramovich had long craved.
With Rafa Benitez serving as interim manager until the end of this season and proving unpopular with fans, the Blues are likely to be looking for a new boss in the summer.
Guardiola is off the shortlist after agreeing to take over at Bayern Munich at the end of the season and Wilkins predicts more widespread difficulties attracting a potential replacement for Benitez.
"Any manager who accepts the Chelsea job knows exactly what they are walking into," he told the Sun. "There is a big salary that comes with the job but also the understanding that you could be relieved of the post at any time.
"I was surprised when Mr Abramovich dispensed with the services of Carlo a year after we won the double and when he sacked Robbie Di Matteo a few months after winning the Champions League.
"In my case, it was 'crash, bang, wallop and off you go'. That's the way he works. If I'd spent £1billion on something, I wouldn't have too many people telling me what to do either.
"Guardiola may well have decided that he didn't want to be in a situation like that. He will have studied the squads at Chelsea and at Bayern and might feel his best opportunities of capturing big trophies at the moment lies in Munich."
Mourinho, who won two league titles, two League Cups and an FA Cup with the club before being sacked in 2007, would be an immensely popular choice with the club's supporters.
But Wilkins continued: "When you employ the biggest coaches in the world, these are people who are going to have an opinion. And because they all now have the luxury of wealth, they're no longer afraid to speak out for fear of getting the sack because they already have all the money they can spend.
"I'd love to see Jose back and so would the fans. The Premier League needs characters like him, and he's a big man for a big job, but there's too much past history between him and the owner at Chelsea."
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