And lo, in 1994, Holistic Design did make a game called Merchant Prince, and it was good. Then Microprose got involved and said, “Yeah, this could be better.” Then many quality of life changes were made, and there was much rejoicing.
In Machiavelli, players take on the role of ruthless trading houses looking to dominate the trade routes of the Renaissance through buying low, selling high, raiding your enemies with hired mercenaries, assassinating the pope, and hiring people to spread rumors that your enemies have venereal disease after burning their house down.
Most of these things can be done in the original Merchant Prince, but Machiavelli adds things ranging from warehouses (that can be burned down) to just making it easier to end your turn.
I played through the game quite a few times in my youth, and still haul it out for occasional playthroughs. At one particularly boring job, I installed it on a thumb drive and played it on my work terminal during lulls. I wish I had the opportunity to really try the multiplayer, for which the game offers hot seat, network, and E-MAIL based options.