Billionaires may be considered paragons of success, but they aren’t all wise investors—especially when it comes to politics. After all, three vied for the presidency in 2020, and none of them ended up in the White House. This year, many of the nation’s tycoons poured hundreds of millions into the battle for Congress, as well as state and local races. It’s still too soon to know exactly how all those bets will turn out, but here are some early winners and losers.