So when the Irishman eventually left Arsenal and moved to Leeds this summer he called in the man who has negotiated every contract he has ever signed. There was no commission, no percentage on any signing-on fee - which is how agents make most of their money - just a solicitor's normal flat fee. Michael Kennedy is the kind of man to give lawyers a good name - and put agents out of business.
Until now he has been the unknown Mr Fixit of British football, even though he handled the biggest transfer in history between English clubs, that of Roy Keane from Nottingham Forest to Manchester United for pounds 3.75m. He came on O'Leary's recommendation, just as he had to Frank Stapleton and Ray Wilkins when they went to Old Trafford. Wilkins has used him for every move since dispensing with the use of an agent at the age of 19.
'My adviser never got me my move,' O'Leary said, 'he just spoke for me. Clubs are delighted to deal with him because they know he's only got the player's interest at heart, there's no cut in it for him, it's not his livelihood.'
There can be no doubt that players need advice, even smarter ones and particularly the younger ones. 'We come out of school early doors at 15, not the most educated of people,' O'Leary said. 'We're earning money in our early twenties that professional people in business are striving to earn in their forties. For all the good advice someone like your dad can give, even he doesn't know the ins and outs of contracts.'
Wilkins said: 'There's always a tendency for players to underprice themselves. No one likes to go in and say I'm worth this or that. Neither do you want to be at loggerheads with a club you're working for, so it's better if someone else does the talking for you, leaving you to do the playing.'
While generally supportive of Gordon Taylor, the PFA's general executive, O'Leary is concerned about its role in transfers where he sees a possible conflict of interests. He has suggested to Taylor that he ought to try professional people like Kennedy working under the PFA's umbrella.Reuse content