When Bill Ackman revealed last month that he was betting the Hong Kong dollar’s peg to the greenback would break, he became the latest in a long line of speculators who have made similar wagers. Nobody has hit the jackpot.

Hedge funds have made bets against the longstanding currency peg going back to the Asian financial crisis. High-profile fund managers including Crispin Odey and Kyle Bass are among those who have previously taken positions that the peg couldn’t last. Ackman’s fund, Pershing Square Capital Management, even once made a bet from the opposite side more than a decade ago. Boaz Weinstein, the founder of Saba Capital Management, is betting alongside him this time.