Jason Calacanis’ Bleak Bitcoin Prediction Draws $3M in Rival Bets—but He Won’t Bite

Three bitcoin investors have thrown down $1 million challenges to Jason Calacanis after he declared the cryptocurrency would never reclaim its record high. One offered a decade-long wager, the other just two years, but Calacanis wants a shorter contest. Adding to the stakes, Hollywood producer and bitcoin educator Terence Michael entered the fray. Bitcoin investor Fred Krueger challenged technology investor Jason Calacanis to a $1 million wager after the All-In podcast co-host declared bitcoin would never establish another all-time high . Krueger opened his challenge by repeating Calacanis’ prediction, “Bitcoin will never break its all-time high again,” before firing back, “Jason, I’ll bet you $1,000,000 that you’re wrong.” His proposal gives bitcoin until Oct. 28, 2036, to exceed $126,210.50, its October 2025 peak.

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