He got too greedy - had bank accounts in his dog's name (and got off with it!) - but the football world had him sussed.
And now Harry 'The Bung' is starting the Premier League season without a club.
The 65-year-old was sacked by Tottenham in June after four years at the helm at White Hart Lane, and the FA told him they would not touch him with a barge pole.
Now he is eyeing events at Aston Villa, QPR, Norwich, and anywhere where the going is tough for the boss.
And let's not forget - this is the man who turned down the Newcastle job by saying: "I thought about it, but there's something not right at that club."
I bet he wished he had the job now!
Harry Redknapp: "I've managed good players at Tottenham and at Portsmouth and at West Ham.
"Honestly, I enjoy working with good players to be honest with you.
"When you've been working with top players it's very difficult to work with inferior players if you like.
"I think I am capable of managing at the very top level so we'll see what comes up.
"England is home to the grandkids and everything else is here - it would be difficult unless it was the right offer (abroad) I really fancied and was a special offer
"Other than that I would look to manage in England in the future.
"I love it, I love the Premier League, I enjoy English football and I enjoy being in England."