Cohen has famously said that he would "take a bullet for Trump", but as more than one pundit has pointed out, your attitude tends to change when you're staring down the barrel of that gun.
Cohen is being investigated for fraud, which may or may not involve Trump. It's serious enough that a federal judge was convinced to sign a search warrant against him - something that has a very high bar when it's an attorney involved and especially one who has POTUS as a client. You can't just walk in and ask the judge for a warrant in order to go fishing - the judge will want to know exactly what you're looking for and why you think you will find it.
Cohen has a wife and two kids, one of whom is about to enter college, and he is looking at huge legal bills that could bankrupt him. The attorneys in the South District of New York are among the best - they know what buttons to push and they've flipped members of the Mafia; flipping Michael Cohen is going to be child's play for them. So the question is not so much if he will flip as it is how long will it take to flip him.
What happens after he flips is anyone's guess. He has been one of Trump's lawyers for about 10 years, but most of what he has done has not really been legal work. He's been the "fixer", the guy who follows the elephant in the parade and cleans up the mess. It's possible that much of what he has done for Trump has never been subject to attorney-client privilege. There is also the crime/fraud exemption to attorney-client privilege, in which the privilege doesn't attach if the client is committing a crime and the attorney is aware of it.
That's what Trump is concerned about. The facade he has carefully constructed for years - lying about his net worth and the types of deals he does - is starting to crumble. Had he not decided to run for POTUS, none of this stuff would have been an issue.
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