Hobson  was assigned to George Blaxland at Merton and in 1833 absconded, although he was apprehended soon after in May.

Hobson was sent to No. 3 iron gang from which absconded on 30th November 1837. He was wanted for several robberies in the Merton area in the following months. He was suspected of taking part in a daring robbery at Invermein with two others on 7th August 1838 and on 9th August also in company with others, he robbed a property at Gyams Creek in the upper Hunter region.

The district was soon in a state of uproar and a correspondent to the newspapers at that time reported that 'bushranging was as bad as ever at New England and it would be some time before the gang were captured unless Government sent a stronger Mounted Police force. He recommended a force to be stationed at Page's or Peels River to save the several days journey to Cassilis. He feared there would soon be worse accounts from New England, as no one was safe there with bushrangers mustering strong well armed and mounted gangs and taking every horse they came across.

In June 1839 Hobson shot and killed constable Fox of the Cassilis Police at the station of W. C. Wentworth at Cream of Tartar Creek near Gammon, and this time an extraordinary reward of almost £100 was offered the capture of Hobson and his associates Francis Knight and John Wilson. (annual wages for shepherd around this time were about £10). A description given at the time reveals that Hobson was only 4'11½" with a sallow complexion; light brown hair; and grey eyes. He had various markings, one being a man's bust on his breast. He had been a farm boy in his native Sheffield.

There were rumours that another bushranger by the name of James Martin, by most accounts a vicious and callous man,  murdered Opossum Jack, as they were known associates. Martin had been seen in possession of the knife, tinder-box, and pistols that had belonged to Opossum Jack who had not again been seen in the district after March 1840.

However in September 1840 it was reported in the Commercial Journal that:-

"Opossum Jack - This notorious bushranger, it appears, lately visited the Mudgee district in company with another of his species, styled "Blue Cap," and two others, not known. They were all armed, as the expression is, "to the teeth," with guns and pistols. It was only about a fortnight ago that this captain of bushrangers had the impudence to stop the lock up keeper of Bathurst, while on the road leading to that township; and it was with the greatest difficulty that he persuaded the murderous fellows to spare his life. They pursed a man named Dunn, who had, it is said, been the principal means of the capture of Lambert and Brown, two bushrangers; and only through the fleetness of the steed upon which he was mounted, there is little doubt but he would have been murdered, as they vowed vengeance against him. Major Nunn, with a chosen band, ought to be despatched after these "murthering vagabones." for with his "nose" he would be sure to scent them out, and it is said he knows the difference between a bushranger in gaol, and a bushranger abroad!

Whether Major Nunn and his force were dispatched as suggested has not been ascertained, however he almost certainly didn't capture the notorious Opossum Jack who must have managed to evade the authorities yet again. If he had been captured, he surely would have met his end on the gallows.

That wasn't to be, however perhaps his end was equally violent. It seems that he managed to make his way north to Gayndah as it was here in 1849 that his luck, such as it was, finally ran out.

In 1853, it was reported that Opossum Jack had died four years earlier, his daring exploits all but forgotten by then. It seems he died not at the end of a noose, or shot by troopers as could have been expected, but at the hands of natives, violently and probably alone on an isolated station many days ride north of his former haunts in the Hunter Valley and Liverpool Plains.