Assuming it crossed the strike price of the deeper put, it could be a few points OTM and right at expiration day or within a few days. so you are at risk at having a shit ton of stock put to your account and not enough equity to cover assignment.
He's not getting assigned inside the two strikes. If so, he would likely be profitable. That wasn't the point. It was a deep ITM assignment of shares resulting in a synthetic long call.