According to a recent report, Steele also tested positive for COVID-19 and she was removed from ESPN's programming for the week.
The former quarterback's comments on social media has people speculating he might be seeking a school board seat.
Cutler recently re-shared a statement from the golfer, supporting four more years of President Donald Trump.
Both parties addressed their alleged relationship online.
"There's one other possibility. It could be an inside job."
Eyebrows were raised when the former Chicago Bears star posted a sweet tribute to his ex-wife on May 10.
Authorities are handling the ongoing case of Michael Cavallari as an active missing person investigation.