The role of a bailiff in the modern criminal justice system is a crucial one, both vital and patriotic. With that in mind, how much does a bailiff make per year? When first becoming a bailiff, you can expect your starting salary to be something around $29,000 per year, the average for entry-level positions. After a few years on the job, you will generally rise to about $34,000 per year, the average bailiff salary. The best-paid bailiffs earn about $46,000 per year, or more in larger cities.