And as owner of JJB Sports and Wigan Athletic Football Club he knows his way around the block.
But he was as frustrated as hell when he turned up for his club's match against principal promotion rivals Ipswich on Saturday and had his day ruined, not by the result, Wigan won 1-0, but by being confronted with a threat of ground closure by the local police authority.
In a long-running dispute Whelan is refusing to pay what he considers extortionate amounts for the policing of matches inside and outside the JJB Stadium, so Greater Manchester police reacted by threatening to take away the ground's safety certificate.
Such a move would also affect the town's famous rugby league club, even though Wigan Warriors never have a police presence on match days. They can't play without a safety certificate.
Now I've never met Whelan, but from what I hear he can be a pretty tough cookie, and when he says, it's not paying the bills that is the problem but the principle, I believe him.
Why should his club have to fork out pounds 43,995 for the policing of the Leeds game, when nearby Preston had to cough up just pounds 7,700 on the day United were in their town?
It smacks of someone not getting their sums right and exploiting the fact that Wigan just happen to have a rich sugar daddy.
I'm pleased a compromise has been found, because closure of such a super stadium would have been a grave injustice.