Henry had been orphaned at eleven years of age and joined the gangs of pick-pockets who infected the City of London last century. He was caught and transported to Point Puer, the penal settlement for boys in Van Diemen's Land.
Bradley had been in the service of Mr George McKay, and O'Connor that of Mr James Gibson when they carried out their first escapade. On the 14th September 1853, they held up Mr Jonathon House and took a double-barrelled gun. From there they went to the residence of John Spinks, tied up all those present and took another double-barrelled gun. They then left for the farm of Mr Staines and after tying him to another man, left. Henry compelled a servant named Smith to accompany them, saying they were dropping off at Mr John House's - next door. At House's they tied up its occupants as usual but House managed to escape through a window. Bradley fired two shots at him but missed. On notifying O'Connor of what had happened, he said that; "they would not be disappointed" and discharged both barrels at Mr Phillips, killing him instantly.
They then went to Atkins farm and after forcing Mrs Atkins to cook them breakfast, they crossed the river to Medwins. Here they took a gun and some provisions and made their plans to cross to the mainland where they were unknown.
At Circular Head, the two men boarded the schooner 'Sophia' and forced the crew to sail them across Bass Strait, arriving at Cape Schanck on Monday 19th September. Two crewman rowed the men ashore at the place now known as Bushrangers Bay, but nothing was ever heard of the rowboat or crew again. From the cape the two villains made their way to Brighton where they went to the farmhouse of a Mr King to get some means of transport. On arriving they found out that all the horses were being used in the field. They approached a ploughman and ordered him to surrender his horses. The ploughman, thinking it was a joke replied; "Come back at dinner time". One of the bushrangers shot him dead.
Bradley and O'Connor next went to Mr Clarke's station and enquired if there was any work for two shepherds. When told them there was none one of them fired a shot at Clarke, the bullet travelling through his hat. A gardener working nearby ran to help Mr Clarke but was stopped short with a bullet through his chest. Six more shots were fired at Mr Clarke but luckily he managed to avoid being shot. The bushrangers bailed up seven men in a nearby hut and after securing a quantity of lead made some more bullets. From there they headed to Kane's Station and held up eleven men and after tying them up ransacked the place.
But by now the police had caught up with Bradley & O'Connor and as they rode into the station the two bushrangers secreted themselves. As the police were untying the men Bradley & O'Connor made a bolt for it. One of the men saw them and cried out; "There are the bushrangers!" Shots were fired one hitting Cadet Thompson in the left breast. The sound of shooting spooked the police horses enabling the bushrangers to get clean away. From there they travelled to Cairn's Station where they raided a tent and took all the provisions therein. Shortly after they bailed up a Mr Ostler and another man and after mounting their victim's horses proceeded to escort them down the road. Now the police party caught up with them once again for after taking the wounded Thompson to Kilmore they resumed the hunt for the two men, On seeing the four men ahead of them the police raced after them and just as they caught up the two bushrangers turned and fired. The police charged straight at the two men and Sergeant Nolan, wielding his sword, made a swipe at O'Connor. In a violent struggle which lasted only a few minutes, the two bushrangers were forced to surrender. On the 24th October 1853, Henry Bradley and Patrick O'Connor were hanged in Melbourne, only forty days after committing their first crime together.