Dash Rendar and Prince Xizor. Everyone is always dismissing Dash Rendar as discount Han Solo, but I still think he could work, make him more ruthless and far more driven by material gain.
Clan Ordo of the Mandalorian.
The Old Republic era.
Dash would work really well in an environment like The Mandalorian, and with the way Dave loves the implement legends material, we could see him in the near future.
The Old republic will 100% appear in canon again. The High Republic is the current goal at Lucasfilm & I feel it is a worthy successor to the OLD old Republic we know from legends.
BTW, Josh Holloway would be my pick for Dash, as he’s got that rugged devil-may-care look that perfectly fits with the character.
Hot damn! Perfect pick! Loved him in Lost. I would like to see him appear across several difference shows, similar to how Hondo appeared in Clone Wars & Rebels.