She was planning to give him the condo as an inheritance after she passed, but now that his girlfriend is expecting a baby, he wants it now!

Giving someone a lot of money doesn’t solve their financial problems if they’ve proven again and again that they can’t be trusted with it. One reason families set up trust funds is that they can’t trust their family members with a large sum of money! If an irresponsible family member has $50,000 in a trust fund, the executor of the trust is not going to give them all of that money at once, and that’s a good thing! If they did, that money would be gone faster than you can say, «Ferrari.» 

If you keep giving sizable sums of cash to someone who spends it all on useless stuff within a year, you have to put a stop to enabling their horrible behavior if you want them to stop. They are not going to change just because you say, «This time, you need to save this money instead of spending it all in one place.» There needs to be consequences for their actions, and if they don’t face financial consequences, they’re never going to learn.