Rahm Emanuel’s bid to become mayor of Chicago may have hit a major road block Monday as one of his major hometown papers is questioning whether he is eligible to run.

The Chicago Sun-Times, in a prominently featured story, points to election law experts who doubt that the former chief of staff meets the qualification of having maintained residency within the city for the last year in order to run.

Emanuel kept his house in the city but chose to rent it out during his return to Washington.

That decision, the Sun-Times reports, may block his candidacy.

Residency “doesn’t mean they must simply own a home in the city that they rent out to someone else,” the paper writes. “They must have a place they can walk into, keep a toothbrush, hang up their jacket and occasionally sleep, the lawyers say.”

The paper also notes though that Emanuel may have an opening to get past the strict requirement.

“Emanuel could argue that he has maintained ownership of the home, voted absentee earlier this year, pays property taxes on his house, lists the address on his driver’s license, registers his car there, and always intended to return,” the report reads.

Emanuel officially announced his candidacy on Sunday and will launch his “listening tour” on Monday.

(Read More: Politico)