Today, his outlay on the club stands at pounds 42m and he flies from his mansion in the Bahamas to every home game.
He is not the type of football chairman who is more interested in the club's share price than its place in the league. His is a true passion, born of an ambition to see Wolves win the FA Cup and promotion to the Premiership before he dies.
But even to those who have witnessed his obsession, The Independent's revelation that, through the club, he is suing his son, Jonathan, 31, over alleged financial irregularities will come as a surprise - raisingquestions about the future of the club.
In spite of the enormous spending on the club ground, Molineux, and on players, Wolves have failed to make Sir Jack's dreams come true. His elder son, Richard, 46, remains on the Board following Jonathan's resignation last year.
Sir Jack is held in high affection by the Wolves fans who much regret that the team has not been able to repay his generosity with good performances on the pitch.
Mark McGhee, the former club manager sacked by Sir Jack, once said: "Sir Jack looks from the supporters' perspective. He's entitled to say: `Hey, I've put pounds 40m into this. This is what I believe.'
"I can't afford to be sentimental but I know what Utopia would be for this club - Steve Bull [Wolves' best-known striker] scoring the winning goal at Wembley, climbing the steps and handing the Cup to Sir Jack."
It is a dream on which Sir Jack will spare no expense - at times to the chagrin of his family. Once, when his daughter, Sue, expressed concern over the pounds 800,000 purchase of a player, he chuckled and said: "She can see her inheritance going down the drain."
Any kind of footballing success would now be a crowning achievement for a man who made pounds 175m by capitalising on the growing popularity of the Bahamas and helping it grow as a shipping centre and an offshore tax haven - he has even based the club's holding company there.
Sir Jack, who was knighted in 1986, has been chairman of the Grand Bahama Development Company Ltd and Freeport Commercial and Industrial Ltd since 1976. He also has interests in electrical and water utilities. He flew with the RAF and is a life vice-president of the Maritime Trust.
Sir Jack lives in an opulent house in Freeport, Grand Bahama Island, with his wife, Jean, and also has homes in Surrey and Inverness. His Scottish place - a 14,000-acre estate - came with the title of the Laird of Dunmaglass.
In spite of his decision to reside on Grand Bahama - for business as well as tax reasons - he likes to portray himself as a great patriot, hence his nickname "Union Jack Hayward". His love of Britain extends to promoting the use of red phone boxes, buses and post boxes on the island.
In Who's Who, he lists his recreations as: "Promoting British endeavours, mainly in sport; watching cricket; amateur dramatics; preserving the British landscape, keeping all things bright, beautiful and British." Following heart surgery two years ago, he blamed his problems on a love of British food. "The cholesterol has built up over the years, I'm afraid," he said. "I'm very fond of fish and chips and big, marbled steaks with all the fat on."
His family members will be concerned over the effect of the row on his health. Those who know them said that Jonathan would go out of his way to be good to his father, to the point of being overly deferential. Following his departure from the club, he prefers to spend time at his farm in Northumberland and is playing no further part in Sir Jack's dream. A business associate said: "They had a good relationship but it has been badly affected by all this business - particularly Jonathan's decision to leave...I don't know how they will survive this, but one wonders what will happen to the club after Sir Jack passes away."
In the meantime, Sir Jack's dream is as strong and obsessive as ever and his haste to achieve it grows ever more urgent.
"I've not got much time to go," he said last year. "My ambition is to lift the FA Cup. Soon I won't be strong enough to hold the bloody thing."Reuse content