Slobbery Jim assumed leadership of the gang with Bill Lowrie in 1853 after three of the gang's leaders were arrested after a failed attempt to raid the brig of the William Watson. However, he had to flee New York City to avoid prosecution for the murder of fellow Daybreak Boy Patsy the Barber. The two had robbed and murdered a German immigrant who had just arrived in the US. However, the pair got into a fight at a criminal dive called the Hole-in-the-Wall over the distribution of the twelve cents taken from the victim. Slobbery Jim wanted the lion's share as he had thrown the man into the river while Patsy the Barber wanted an equal share as he had bludgeoned the victim in the first place. Slobbery Jim tried to bite Patsy the Barber's nose off while Patsy the Barber tried to stab Slobbery Jim's throat. After a lengthy fight, Slobbery Jim ended up cutting Patsy the Barber's throat before stomping him to death with his hobnail boots.
Slobbery Jim is believed to have ended up in the southern United States where he rose to the rank of captain in the Confederate States Army.