“I have chatted with many Obama supporters who tell me Beto is a rock star, and if he decides to enter the race, I would be excited to meet him,” said Robert Wolf, the former chairman and C.E.O. of the U.S. arm of UBS, the big Swiss bank, and the founder of 32 Advisors, his own investment boutique. Wolf, who rose to national prominence a decade ago for his financial and intellectual support of a then-obscure candidate named Barack Obama, has since become perhaps the most sought-after Democratic executive on Wall Street. As dozens of candidates begin revealing their 2020 ambitions, he has already become a key stop on the rapidly escalating “money primary,” during which hedge-fund managers, private-equity moguls, and banking executives nourish a new generation of political hopefuls with advice and money. “I have been friends with many of the potential candidates,” Wolf said. “I’ve already met with a bunch of them or talked to them about their plans to enter.”

Wolf explained how he’s approaching what would appear to be a complex nomination process—one filled with conflicting ideologies, big names, and newcomers—all in the hope of unseating Donald Trump. Naturally, coming from Wall Street, he seemed inclined to hedge his bets—at least for now. “There's no need to go all-in on someone this early especially when many haven’t even committed,” he said. “If you have a group of people you know really well, at the beginning you can sprinkle your support around, but as the process matures you will have to get behind one, maybe two candidates in a real way.”

In Wolf’s estimation, there could be as many as 25 different hopefuls on the Democratic side, with various groups of candidates having their own lanes, and their own narrow constituencies. It’s quite possible that for many months no one will get above 20 percent support, he continued, until the field winnows sometime after the debates begin this summer. As it currently stands, the prospective candidates break down into about a half-dozen categories, from the billionaires (Michael Bloomberg; Howard Schultz) and the longer-shots (Julio Castro, the former HUD secretary; Pete Buttigeig, the openly gay mayor of South Bend, Indiana) to established players on the far left (Bernie Sanders; Elizabeth Warren) and to a new wave of contenders (such as O’Rourke, Kirsten Gillibrand, Cory Booker, Sherrod Brown, and Kamala Harris). And, of course, there is the former Vice President Joe Biden, who occupies his own unique category.

The consensus on Wall Street, at least at this moment, seems to be that it’s all going to come down to a battle between Warren, Sanders, Biden, O’Rourke, and either Gillibrand, Booker, or Harris. (For what it’s worth, while Wall Streeters also love the idea of the 76-year-old Mike Bloomberg as president, most don’t think he has a realistic shot of winning the Democratic nomination; he is simply too much of a centrist businessman.) “You have to think about this differently than in past elections with so many running,” Wolf said. “You have to look at it much more as a game of chess, where one move by a candidate impacts many of the other pieces on the board.”

Wolf knows and likes Harris a lot. He also thinks O’Rourke, who is 46, has youthful charisma on his side, noting that during the past six decades, the Democrats had succeeded only in electing candidates 53 years old, or younger. But the Biden question looms large.