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On The Brink with Castle Island


Jun 5, 2026

Matt and Nic are back for another week of news and deals. In this episode: 

  • FIFA’s World Cup ticketing scandal
  • Andrew Yang is now a crypto and telecoms entrepreneur
  • Are Strategy’s woes responsible for the Bitcoin pullback?
  • Will Saylor defend STRC or MSTR?
  • What are Saylor’s options here?
  • Polymarket has another market resolution SNAFU
  • How UMA could be used to exploit Polymarket
  • BitMine considers a perpetual preferred security
  • Google’s quantum circuit is optimized by hobbyists
  • Galaxy launches OTC trading for prediction markets
  • Treasury sanctions Iran’s largest digital asset exchanges
  • Andrew Left of Citron research is convicted of securities fraud