Gilligan (55) found from an early age there was more money to be made from crime.
He had secured the first of his sixteen criminal convictions as far back as July 1967, when he was given the probation act at on a charge of larceny.
His first experience of Mountjoy jail was in 1977, when he was given an 18-month sentence for receiving stolen goods.
Ten more prison sentences were to follow, before he released from Portlaoise jail after a four-year jail term.
While Geraldine struggled with the mundane problems of meeting her weekly bills, Gilligan had been working out a plan that would see him provide her with the life she desired.
Gilligan had established himself as the head of a gang that specialised in robbing warehouses but discovered in jail there were easier ways to make money and they all centred on drug trafficking.
Shortly after his release from prison, he embarked on a criminal enterprise -- smuggling cannabis into Ireland -- that would make him and Geraldine into a wealthy couple.
Garda inquiries estimated he had grossed about €16.8m from drug-dealing between early 1994 and October 1996.
At the same time, he was also engaged in smuggling guns, some of which were stored in a grave in a Jewish cemetery in Tallaght.
The weapons were to be used by the gang to intimidate potential criminal rivals and as part-exchange with paramilitary groups, such as the INLA, to discourage their interest in his gang's distribution network.
Faced with a massive cashflow, he began gambling to launder his money. But it was the purchase of the Jessbrook equestrian centre near Enfield, on the Kildare-Meath border, that tickled Geraldine's fancy.
She had finally acquired her dream home and for the past nine years has fought to prevent the Criminal Assets Bureau from taking it away from her.