I don't gamble, but if I had mad money around that wasn't needed elsewhere, I'd like an engraved Colt Single Action in 44 spl, or a tightly chambered 45 Colt. A modern Colt flat top target copy or New Frontier may be good, with the front sight swapped out for a copy of the Flat Top Target front sight. A little gold inlay work on the edges would be fine. It would get carried and used.
"Far better it is to dare mighty things, to win glorious triumphs even though checkered by failure, than to rank with those poor spirits who neither enjoy nor suffer much because they live in the gray twilight that knows neither victory nor defeat." -Theodore Roosevelt-