A less positive person might have wondered whether someone up there had it in for him. Not only did Freedman's Scotland career take a nasty kick in the Baltics when Estonia left them all dressed up with no one to play, but he has twice been offloaded from the Premiership after a grand total of two starting appearances.
Even now, despite being leading scorer for Wolverhampton Wanderers with a highly respectable 12 goals in 27 matches, Freedman has found the Molineux crowd slow to warm to his talents. His crime, like many a Wolves striker over the past decade, is that he is not Steve Bull.
During our conversation, I was holding forth about what it is, apart from a trifling 300 goals, that makes "Bully" such a working-class hero: "He chases everything, balls other players regard as a waste of energy," I said. With a mixture of self-mockery and honesty, Freedman cut in: "And I don't."
The 24-year-old Glaswegian, blessed with some of the ebullience of his adolescent idol, Ally McCoist, loses no sleep over invidious comparisons or claims that he does not charge about enough. "I came here to play the way I can play. People either like it or they don't. If I keep scoring, the style won't matter to them."
Were he to settle today's quarter-final tie at Leeds United, Freedman could get away with playing the next fixture sat in an armchair and puffing on a cigar.
It would certainly confirm his talismanic status in Wolves' FA Cup adventure. Having scored at Darlington in the third round, he wrecked Wimbledon with a stunning late solo effort at the last stage.
Yet his importance to Mark McGhee's side in their quest to gain promotion from the First Division and/or reach the Cup final is replete with irony. His two goals in the play-offs last May helped take Crystal Palace to Wembley at the expense of none other than Wolves.
Palace's eventual victory over Sheffield United restored Freedman to the level he had left when Queen's Park Rangers - where he understudied the likes of Les Ferdinand and Roy Wegerle - freed him to Barnet.
A prolific strike-rate for the club with the bizarrely sloping pitch earned Freedman an invitation from the Palace. His initial success there prompted the Scotland manager, Craig Brown, to take him to the double- header with Latvia and Estonia 18 months ago.
"We got to Tallinn for the second game and Craig told me I was substitute and there was a fair chance I'd come on. But when kick-off was switched from the night to two in the afternoon, the Estonians decided not to show. At five to two I was still hoping to see their bus coming through the gates."
Freedman's Law meant there was an inevitability about his absence from the rematch in Monte Carlo. Promotion to the Premiership with Palace eased the disappointment, but after only spasmodic outings this season - including a bit part in a win at Elland Road - he was transferred to Wolves.
"I was getting stale at Selhurst. Things weren't happening for me. I liked the club at first, but things started changing. They were bringing a few foreign stars in." Freedman argued, with no obvious sour grapes, that Palace's imports had struggled with the "hard slog, games every three or four days" of an English season, adding: "It's not their fault - they're not used to it."
Away from the Cup, Wolves' own form has been patchy. Their best hope now looks to be the play-offs, which is also familiar territory for the player leading Leeds today. Freedman's compatriot and former room-mate, David Hopkin, was another scorer for Palace against Wolves last spring and also decided the final, though he has not made the expected impact in Yorkshire.
"George Graham has got him doing more of a holding role, whereas at Palace he had the freedom to do what he wanted - bomb on, set up goals, score them. I know what he can do, so I'll be happy if he just sits in the midfield and breaks things up."
The pair remain close friends. "I spoke to Hoppy the other day and we agreed that there'll be no room for mates once the whistle goes. Leeds will be confident, being at home, but I sense a determination in our dressing- room that this won't be the end of our Cup run. In this competition, home or away doesn't really matter.
"Our best chance is to keep it really tight, give nothing away, make it boring - no entertainment at all - and try to nick a goal. We've got a very strong defence."
Tongue may well have been tickling cheek as he spoke, for his instincts as a player are purely attacking. Besides, there is an outside chance of a place in the World Cup finals this summer. Failing that, the European Championship qualifying draw has provided Freedman with the ultimate incentive - a return to Tallinn.Reuse content