In 1998, Riley finally retired from the canine division to spend more time with his family and focus on working at the troopers' station in New Woodstock. Riley was head of administration in New Woodstock. He also served on the Gaming Unit for Turning Stone to run criminal and background checks on large corporations that the casino did business with, as well as screening managerial applicants.
In 2007, Riley started to work for the Oneida Criminal Investigators when he was thinking about running for sheriff in the next election. Longtime friend of Riley's, former Sheriff Cary, told him he was thinking about retiring in 2009 and that he should think about running.
With a future candidacy in mind, Riley continued working on high profile investigations in Madison County and some parts of Oneida County dealing with felonies, child abuse, homicides and other cases that needed investigating.
"I wanted to get back into working just the county," Riley said. "I wanted to prepare for giving the [sheriff's] department a fresh start; change is a good thing."
Because he has worked in several areas of law enforcement in different locations, Riley said he would like to bring "community policing" into Madison County.
"It's about meeting people and putting [sheriff's] deputies at events, big and small to show our presence and get to know the community."
Riley would like to see community members become comfortable with the sheriff's deputies to a point that they can call and let them know if there is something criminal going on in their town or village, without hesitation. "A lot of crimes can be solved by talking to people," Riley said.
If elected, he would also like to see more recruitment in the department. "With the economy the way it is, there are probably some highly qualified people out there that are looking for a [law enforcement] job," Riley said.