Trump's January

Behind him we see losses due to constraints and unexpected expenses. We don't know specifically what the loss is since it would be shown behind the thief's back.

Theft takes on a different meaning in the top row. He could be thinking about taking something to put an end to a constricting situation that has him feeling oppressed. The foot of the Coffin points to Prison. But it could also mean he's taking something to separate someone or something and put constraints them. The result would be them having a feeling of oppression which might elicit whatever cooperation he's trying to bully them into. It could go either way with him but is more likely the former.

In front of him is something new. Gloomy Thoughts here could be something secret or fraudulent. Something new. A desire he's fulfilling. It would be something he's aspired to for a while and has now put into action or is now coming to fruition.

The same thing is shown in the bottom row. Something is really working out in his favor. Whatever's going on behind or above him will ultimately have a positive outcome. With the Unexpected Money card, whatever expenses he's been having could be turned around into a gain or improvement for him.