I am, sadly, pretty unsurprised that I’ve never seen politician!Lando in fandom before, because in general the Star Wars fandom (and the Expanded Universe) seems to characterize Lando largely on the basis of a single statement from Han Solo about him.
Han tells Leia that Lando is a card-player, a gambler, and a scoundrel, and the Expanded Universe took that and absolutely ran with it, and, possibly because of the EU, fandom has taken it as gospel truth, too.
But the thing is, that’s only what Han says about Lando. It’s not at all what we actually see of Lando on screen.
The Lando of ESB is, in a word, responsible. That’s how he characterizes himself, a bit ruefully, and it’s borne out by his actions throughout the movie. He’s clearly been a very successful businessman for a while now, and he’s just as clearly respected and liked by the people of Bespin. He tells Han and Leia that he’s one of the few gas mining operations that’s still independent, and he’s clearly proud of this fact. He’s just as clearly invested in the work that’s being done on Bespin. He doesn’t just own the operation. He very obviously cares about it, and about the people who work for him. His decision to give Han, Leia, and Chewie up to Vader is ultimately an effort to save as many people as he can, made because he knows he’s caught between a rock and a hard place but, no matter how much he cares for Han, he is the administrator of Cloud City and the lives of everyone there are dependent on him. He’s responsible for them, and he’s willing to risk himself to protect his people. Only after he’s done all he can to protect them does he allow himself to try to help Han and co.
And when we see Lando again in ROTJ, he’s joined the Rebellion and been commissioned as a general. A general. For a guy who, so far as we know, has held no prior military rank, and who joined the Alliance maybe a year ago, that says quite a lot. Clearly, he’s committed himself to this rebellion - and he’s proven himself, both as a rebel operative and as a leader. From what we see of his interactions with his fighter squads, the other rebel pilots seem to both like and respect him.
So maybe Han is right, and at one time Lando was a card player, gambler, and scoundrel. But that’s clearly in his past, and the Lando we actually see on screen isn’t a scoundrel at all. He’s a respectable and respected businessman and city administrator, with an impressive military record and quite a few well-placed connections in Alliance leadership. He’s shown a definite aptitude for administration and civic leadership, and always puts the people he serves first even at great risk to himself.
In short, he’s excellent material for political office.
Lando Calrissian for Republic Chancellor 2018.