TOM HUNTER, Scottish retail tycoon and a man who appreciates plain speaking, has messed up of late. House of Fraser, Allders, Selfridges — all bid for or stalked in the past six months and all missed. Hunter may have made a fortune building up and selling his Sports Division chain in the 1990s, but recently he has failed to nail every big-name target he has set his sights on.

And his reaction? He grins. “If you think the feeling of losing is bad,” he says in his broad Scottish accent, “the feeling of overpaying and having debt wrapped round your bollocks for the rest of your life is infinitely worse. If somebody outbids me and I think their price is wrong and my price is right, then I will walk away.”

Last week he did just that — again — this time conceding defeat to Galen Weston, the Canadian store mogul, in the bidding for Selfridges. After his December run at House of Fraser (bid withdrawn after management refused to show him the books) and a February dalliance with Allders (hoping bidder Minerva would split off retail interests, which it didn’t), Hunter is beginning to look like a department-store kerb-crawler, always on the lookout for action but never quite managing to get the goods.

Does he feel he’s missed a trick? “Noo, I am 42 years of age, I’ve got a few quid in the bank, and we are playing in a sector where there are opportunities every second of the day. Missed out? F*** that. I hope I miss out like that every day for the rest of my life.”

For the truth is, Hunter makes money on the stakes he sells on — about £8m on Selfridges alone. But it’s still not the same as bagging the prize. Ask his friend and mentor Philip Green, boss of BHS, who, in contrast to Hunter, seems to have swept all before him recently. “Sometimes,” says Green, “it takes a brave man to bid, and an even braver man to walk.”

Green advised Hunter on the Selfridges bid, finding him bidding partners and counselling him on his exit. That relationship goes back a decade, when Green helped Hunter take the Olympus sportswear chain off Sears to add to Sports Division, and developed a close relationship in the process. Some have portrayed Hunter as a wannabe-Green, but if he keeps shooting and missing, that reputation will be dented.

Hunter says he doesn’t care, and the setbacks certainly haven’t effected his wryly affable demeanour. Shaven-headed, blond-goateed, dressed in pressed jeans, blue jacket and designer shirt opened just enough to frame the discreet silver crucifix glinting on a leather thong, Hunter looks more like a rock manager than a retail tycoon. Sitting on a sofa at a private members’ club in London, peppering his anecdotes with those muscularly macho adjectives that are so popular with retail big-hitters, Hunter shrugs off any concern that he has been playing out of his league.

Reputation? Bollocks again. “I tell you, if you turn up with 700m f****** quid in the City they don’t care if you’ve got three f****** heads, they just want to see the £700m.”

Three flops on the trot? Oh come on, he has time and cash on his side, he’s a fast learner, he’ll be back — maybe sooner than you think, as he has a chance to take another pop at House of Fraser in July.

Will he? He can’t say, bound by Takeover Code rules, but maybe a bid is not so attractive now. He had his eye on putting House of Fraser and Allders together, there was synergy there, savings to be made. Now that can’t be done, perhaps he will finally walk away from House of Fraser too.

And he does have other fish to fry. Since he sold his trainers-to-shell-suits chain Sports Division to JJB Sports for £290m in 1998 he has bundled money into retail parks, shopping centre management and property development, working closely with a posse of friends and partners: BHS and Arcadia owner Green, property specialist Nick Leslau, corporate banker Peter Cummings at Bank of Scotland, and former Price Waterhouse Coopers tax adviser Jim McMahon, who now helps run West Coast Capital, his investment vehicle. They have helped Hunter turn the £260m he made from the Sports Division sale into wealth estimated at £425m and rising.

And he’s not slow to spread it around: £10m has been piled into a charitable foundation that invests in educational initiatives in Scotland to which Hunter is passionately committed.

But his fortune may not be enough. What puzzles Hunter’s friends is how he seems torn between establishing himself as a major retail player again, yet remaining close to his Ayrshire roots. He lives near his parents outside Glasgow, and his dad, who used to run the local grocery store, works in the West Coast office every day — “he’s in charge of the chequebook,” laughs Hunter. He still sees his mates from primary school. “Aye, down the chip shop with them on Sunday nights.”