Options Boot Camp 402: Double Calendars and the Fall of Constantinople

What do double calendar spreads and the Fall of Constantinople have in common? More than you might think. On this episode of Options Boot Camp, Mark Longo and Dan Passarelli use a memorable historical analogy to explain one of Dan's favorite advanced options strategies: the double calendar spread. The discussion covers: What a double calendar spread actually is Why it can be viewed as a "strangle swap" How Dan structures weekly double calendars When he typically enters and exits the trade Why wider breakevens aren't always guaranteed A recent SPX double calendar example Managing profits and avoiding common mistakes Then it's time for listener questions covering: Selling cash-secured puts versus covered calls near market highs Trading calendars and diagonals during earnings season Whether buying options into earnings still makes sense Scaling into positions Weekly SPY options and whether traders are sacrificing edge for more opportunities