I'm not at all sure Trump "feels dead inside". He's certainly capable of finding enjoyment and amusement in a variety of ways, I'd say. But now and then he's unsure of himself. He knows people laugh at him, and sometimes he suspect why: "Smart people don't like me".
But I believe he can suppress those thoughts most of the time.
Congress has imposed various restrictions on the ability of Treasury to feature living people and living presidents on currency. It’s not clear whether the latest Trump coin envisioned by the Treasury Department would run afoul of those laws.
I do not think any living person has ever been portrayed on a U.S. coin. The only presidents have been DEAD presidents. Perhaps Trumpty would do well to consider that.