Wall Street traders are scrambling to position portfolios ahead of President Trump's 8 p.m. deadline for escalating attacks on Iran, with many preparing for both de-escalation and potential military strikes. Ariel Itzhak, a Miami-based retail trader, said he's betting against any market rally as uncertainty grips investors. The S&P 500 slumped around 0.5% while oil futures surged above $115 a barrel following U.S. strikes on Iran's Kharg Island.

Since the conflict began six weeks ago, monitoring the president's shifting ultimatums has become essential for both Wall Street professionals and individual traders. The volatility has created a unique challenge: Trump's pattern of backing away from extreme policies has spawned its own acronym—TACO (Trump Always Chickens Out). This unpredictability has left many investors mentally exhausted, with some choosing to stay on the sidelines until a concrete development emerges.

Traders like Itzhak are spending days tracking social media for signs of policy reversals while trying to anticipate market moves. The constant drip of headlines has created a trading environment where preparation for both de-escalation and escalation has become the new normal. As uncertainty persists, many investors remain wary of committing to major trades until the conflict reaches a definitive resolution.