Monday was one of those days in the market that reminds you why they call it "trading" and not "sleeping." The SPDR S&P 500 ETF Trust (SPY), which tracks the S&P 500, went on a wild intraday ride. It all started with oil near $120 a barrel and the broader market down over 2%. Then, a sudden claim of military victory from President Donald Trump flipped the script, sparking a massive short-term rally. But here's the twist: while traders were celebrating, the market quietly tripped a technical alarm that has, in the past, been a pretty reliable signal for a bear market.

A Historic Options Squeeze

The real drama wasn't in the stock prices; it was in the options pit. Let's set the scene: by 2:10 p.m. ET, things looked grim. The SPY call options with a strike price of $675 had basically been left for dead, trading for a mere $0.02 per contract.

Then, at 3:20 p.m. ET, comments from the White House hit the wires. By 3:30 p.m. ET, those same worthless-seeming calls were suddenly worth $4.95. That's a gain of 24,650% in roughly 80 minutes. To put that in perspective, data from The Kobeissi Letter shows a $1,000 bet placed at the afternoon low would have ballooned to $247,500 by the closing bell. It was one of the most dramatic intraday reversals you'll ever see.

Trump Declares Victory

So, what was the catalyst that turned pennies into fortunes? President Trump signaled a major turning point in the ten-day conflict with Iran.

"I think the war is very complete, pretty much," Trump stated, adding that the U.S. campaign had successfully degraded Tehran's military infrastructure. "They have no navy, no communications, they've got no air force. Their missiles are down to a scatter." He further noted that the operation was running "very far ahead of schedule."

In market terms, that was interpreted as a de-escalation of geopolitical risk, which sent a shockwave of relief—and speculative frenzy—through trading desks.

The 20% Technical Warning

But before you get too excited about those options gains, here's the sobering part that institutional analysts are whispering about. Despite the afternoon party, the SPY closed below its 100-day and 20-week moving averages. Not just for one day, but for the second consecutive session.

This isn't just a minor blip on the chart. Gina Martin Adams, Chief Market Strategist at HB Wealth, pointed out that this specific technical breakdown has only happened eight other times in the last decade. And history isn't kind when this floor gives way. A similar failure of this key trend level back in February 2025 was the opening act for a nearly 20% market crash.

Think of it this way: Trump's comments provided a powerful, adrenaline-fueled bounce, but the market is still technically lying in a bed it has historically gotten sick in. The index remains trapped below this critical level, leaving the door wide open for a full-scale correction if the initial relief rally fades.

For the record, the major ETFs did manage to close in the green. The SPY finished up 0.88% at $678.27, and the Invesco QQQ Trust (QQQ), which tracks the Nasdaq 100, advanced 1.34% to $607.76. But those closing prices are still sitting underneath that ominous technical ceiling. Monday was a tale of two markets: one celebrating a short-term victory, and the other quietly flashing a long-term warning sign that's hard to ignore.