Usually these poll questions are no brainers, but I think this is actually a damn tough one.
I'm voting no, because I think it'd be less than 50/50 to happen, but I could definitely see it happening if we do get in the playoffs.
I do think the scenario in which this happens is if the team has a stronger playoff performance than last season, Cutler miraculously stays healthy all season, and has a career year. In that scenario, I think Cutler would definitely want to continue playing instead of heading into retirement, and Gase 100% strikes me as a "Bird in hand is worth two in the bush" type of guy.
But those are a lot of IFs that go beyond "if Miami makes the playoffs."