Big handlebar moustache and slightly overweight, or a whole different look? (I say it's not Harry if he looks different.)
I always thought it would have been better to make Mudd something like Kirk, if Kirk had remained a ne'er do well. Just as clever and capable and even brilliant in his own way, tested similarly well as a young man, but just went a very different path in life. Something of a mirror for Kirk.
He should be
very difficult to catch or outwit. An escape artist. All of this would make him an altogether more formidable guy. And this could all be done without losing all thats basically devilish and fun about the character. He should certainly not be a campy oaf or just a sleazy grifter.
As for his look, he could retain something of a pirate-esque/Buccaneer look and even be a bit overweight. But I think its definetly important to get his character right.
Good stuff
Tarek71 !!

Very cool idea, finally, someone who understands character development !! They could make a whole movie on this version of Mudd, or at least a secondary storyline that influences or holds together with the main plot.
Thank you. I would like for Kirk and Mudd to see "the road not taken" when they see each other. Maybe Mudd never had a talk like Kirk got from Pike, or maybe he did and just decided, on second thought, to say "F that!", "F the rules".
And I think they should share Kirks wanderlust. They may both try to settle down at some point, but in the end the pull of deep space and being "out There" is too strong. For Kirk, its that chair on the bridge of the Enterprise. For Mudd, it might be the Game, the Chase, the Challenge. High stakes and adventure.
If Kirk were out there trying to evade Starfleet security and pull off capers, how tough would he be to capture? Thats what Mudd should be. Even in a small underpowered private starship, he could be very formidable.
Of course, you dont want to diverge too much from the TOS Mudd, otherwise it might be better to just create a new character in the tradition of Mudd, Cyrano Jones or even Han Solo. But I think this can be Harry.
As for the story, its hard. I think the androids of I, Mudd could of been written very differently. Much more menacing.
They could have been a major new threat and enemy of the Federation. I certainly hope we wont see Kirks famous ability to talk robots into self destructing in the nuTrek. That goofy way that they stopped the androids shouldnt have worked.
But ultimately I am not sure nuMudd should be introduced that way. But there are certainly possibilities.