RE:pot, gay, jail...I believe there is more money to be made with the MJ business. The prison are getting paid by the government for each criminals inside, I suppose that if the Warden has some politicians/Judges buddies, they'll get a cut, but in the end, the government is losing cash. In the other side, with the MJ business, the government could put a tax on that and earn money off of it and for those "corrupted" people, they could allow some contracts to benefits some people.
Now, I'm not claiming that the government is corrupted, but I believe I've heard cases of false imprisonment to feed the warden's pocket, so it is a known issue.
Conclusion, there is much more benefits for the government to legalize MJ, but I may understand that Trump may want to flip it around to make it look like he's the one that's allowing it to happen so he could earn those votes like you've mentioned.
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