But current President Toni Preckwinkle's administration has contested the claim with the state's unemployment agency, the Chicago Sun-Times reported, citing a source from within the administration.
The "application was protested because, as a former elected official, he is ineligible," source told the Sun-Times.
"The salaries they earn for the duties they are elected to perform do not count toward those (unemployment) wages," Greg Rivara, a spokesman for the Illinois Department of Employment Security, explained to the Chicago Tribune.
If he does lose his bid for unemployment benefits, Stroger will have the option to appeal his case in circuit court.
Stroger earned $170,000 annually as board president. If he'd worked as a regular county employee or in a private sector, he would receive about $530 per week in unemployment, according to state law.
However, since his job was an elected position, it's as if he didn't work at all, or earn any money.