The best money road player has got to be one who can match up and handicap well, which requires knowledge and expertise in all games of pocket billiards. This is the most important trait (IMO).
And it goes without saying, it does help to have the gift of gab, or "woofing" as it is sometimes called, to get it going. Action doesn't drop out of the sky without a little barkfest. This is where the human behavior becomes interesting.
One necessary requirement to be a big money player is to have, well, lots of money, and when without, the empty-pocketed smart road player will seek funds through other means, i.e., stakehorse, form a backers committee, seek a partner whose pockets are deeper than his or hers. A good road player has to be creative when conjuring up action and does need to adapt his promotional strategies to suit the setting. Most of the very high-stakes action aren't self-funded, for lack of a better term.
I know who my favorite "best money road player" is, but I think I've got to throw in a few others. The biggest money game I ever heard of was with some guy named Rosey from Detroit who used to enjoy games of high stakes.
Other astute and worthy mentions go to Weenie Beanie, Louie Roberts, Ronnie Allen, Cornbread Red, Larry Lisciotti, Wade Crane, Jimmy Mataya, and Buddy Hall. Two areas of the country that used to rock in action in days gone by were Detroit and New Orleans, with a few pockets in California and Texas.
There's a few young gun players in my area who aren't afraid to bet it up, but there's nowhere near the action today that there was 20-30 years ago. Best handicapping road player today (IMO) is Danny Basavich. Whatever he's betting on, go with him.
This is why the Derby City Classic is such a nice tradition for players of all ages. Hope there will be more updates, like who's staying in action non-stop. They will award the St. Louis Louie Roberts Award to the most entertaining player, free entries for life to all DCC's. The first year, Alex Papulayan won it, and last year North Carolinean Tony Watson got the honors.
JAM