THE chairman winced.

Yet another Dundee United player was posing with the Scottish Cup. This is a minor offence to Stephen Thompson's sensibilities.

He is a man who was fated to inherit the custodianship of Dundee United but he is also a character who frets and fidgets in the seat of power. The majority shareholder at United carries the same neurosis as the most humble of fans. A player holding a cup before a game is inviting the wrath of the sporting gods.

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Thompson has been following United since the age of four but the intervening years have not calmed him as the big match approaches. It can be stated with certainty that he spent a sleepless night last night.

"My mind tends to work overtime," he says. It is likely that he reprised this morning the walk on the shore he took before the William Hill Scottish Cup semi-final with Rangers.

As a fan, Thompson suffers. As a the majority shareholder, he has cause to be content. "I've been chairman for five-and-a-half years and the club is at its most stable during that period. We don't need to worry about the cashflow between February and March when things are tight in football," he said.

"Every player, except one, has at least two years left on his contract. Unless the offer is right in the summer then we won't be selling and we're looking to bring others in. Jackie [McNamara] and I have been talking about five players in the last three or four weeks."

This statement, made in the environs of the Old Course of St Andrews, is one that strays into the out of bounds of Scottish football. A club that does not need to sell? A club that is looking at five players? And Thompson raised the stakes even higher by pointing out there was even a contingency transfer fund.

His relationship with the manager is also sound. They regard each other as friends. "He's a clever guy and we talk three or four times a day. We talk about family - he's got a 16-year-old daughter and I've got an 18-year-old and four-year-old - football and business," says Thompson. "I let him understand the finance of the club because I think that's a huge benefit to any manager. I don't think every manager wants to know the bigger picture but if you can then you can do your job in a different way.

"We just extended his contract three months ago, put an extra year on it and dealt with his salary," he said. "One or two people said I was a bit quick but when you're working with someone every day you learn about their qualities." One of McNamara's defining traits is that he "buys in" to the club's policy of nurturing and playing young talent. Thompson may not have to sell in the summer but such as Nadir Ciftci, Stuart Armstrong, Andrew Robertson, Ryan Gauld, John Souttar and others may attract offers that cannot be resisted.

Whatever happens, there is a vision at United and the dark clouds of debt and financial uncertainty do not darken it.

Thompson, though, is aware of how short-term football can be. United won the cup four years ago and a painting of the team hangs in his office. Only Sean Dillon and Keith Watson remain at Tannadice from that side. The team now hums with the vim and vigour provided by a tranche of promising youngsters.

"It would be great to get another year out of them," he says of that cadre of talent. "A lot of our kids are in no rush to go anywhere. They realise that they've got another year of first-team football under Jackie which could be the best for their development. "

He pauses before reflecting: "I just keep wondering what Ryan Gauld, Stuart Armstrong and Andy Robertson will be like in four or five years if they keep developing and maturing. There's no doubt they won't be with us but they're great players with great futures."

United's future ambition is to continue to reach cup finals and finish higher in the league.

Thompson concedes that competing for the title with Celtic remains fanciful but both he and the manager believe there can be improvement on the fourth place finish this season.

Next season too will provide the renewal of the derby. "Dundee coming back up is big for the city. Massive financially," he says. "We could play other teams in the league 10 times and wouldn't take the same income."

He speaks as a fan when recalling watching the likes of David Narey and Paul Hegarty. He talks as a chairman when reflecting on the income streams, the wiped-out debt and the ability of Scottish football to be both vibrant and viable.

But he also is a son and he spoke of his late father, Eddie, who took over the club in 2002. Thompson Sr was the founder and chief executive of a chain of shops that he ended up selling for £30m. He ploughed his money and his energy into United before his death in October 2008.

"Hopefully my dad would be proud of what we've achieved since I took over. I don't think about it that often but two cup finals and getting rid of the bank debt is hugely important for the club," says the son who inherited both turbulence and controversy when he took over at Tannadice.

"We're in the best place [we've been] financially for about 18 years. I think for fans of clubs who are stable, the fans kind of forget about it, but you still need them to support the club."

There will be a financial windfall today that would bring a smile to any businessman's face. But Thompson the supporter will have lost a night of sleep.

Only silverware this afternoon will address that deficit.