Former housebuilding tycoons Michael and John Taggart's property portfolio once extended to a Luxembourg shopping centre and luxury apartments in Florida and on the borders of Monte Carlo, the High Court has heard.
As the businessmen's multi-million pound legal battle with the Ulster Bank got under way in Belfast, a judge was told how they built up huge profits in up to 40 site purchases and sell-on deals.
Giving evidence at the start of a case expected to last for three weeks, Michael Taggart set out his career path in the construction industry from purchasing a plot for one house to winning entrepreneur of the year and sharing a tent with a senior bank executive on a trip to the Dominican Republic and Haiti.
Details were also disclosed of three major joint-venture acquisitions involving hundreds of millions of pounds before the fall of their property empire.
The brothers are suing the Ulster Bank for alleged negligence and improper conduct they claim contributed to the destruction of their business.
The Taggart Group was once one of Northern Ireland's largest companies, with operations in England and the Republic of Ireland.
But following the property crash in 2007 it eventually collapsed and went into administration, costing creditors hundreds of millions of pounds.
In a counter claim, Ulster Bank has lodged writs for £5m and €4.3m it alleges the brothers owe in personal guarantees over land purchases in Kinsealy, north Co Dublin, and in Northern Ireland. The brothers deny both claims.
Central to the Taggarts case is an allegation that the bank did not properly warn the brothers of concerns about the financial status of their business at the time.
Had the brothers known of any unease, they contend, there were plenty of assets at their disposal which could have been sold to off-set loans.
In his evidence Michael Taggart told how he started off in construction at the age of 16, overseeing his first development sites in the Londonderry area in the late 1980s.
Alongside his bricklayer brother John, he set up the Taggart Group which included more than 70 companies by time it went into administration in 2008.
Once described as Ireland's richest man, Mr Taggart (48) said he had enjoyed an open, transparent relationship with senior bank staff.
He recalled going on a conference trip to the Dominican Republic and Haiti in May 2007 as a nominee for a businessman of the year award.
"There were two senior people from Ulster Bank on the entire trip; everybody was hanging out with everybody throughout that entire trip," he said.
"I stayed and shared a tent with a guy who was very senior."
Mr Taggart set out how Taggart Group and a stockbrokerage were involved in three major joint-venture acquisitions involving other banks:
● A £75m deal for Frazer Estates Ltd in 2006 which included £5.75m put in personally by him and his brother.
● A £100m fund for a project referred to as Belfast II the same year.
● A 1,000-acre site in Dundonald, outside Belfast, bought for £96m in 2007. The hearing continues.