To The Moon

• The 4,000 level for S&P 500 is a battlefield for bulls, bears
• Cboe put-call ratio for single stocks reaches a 25-year high

Nowhere better illustrates Wall Street’s febrile sentiment than the stock-derivatives market, where trading volumes are breaking records heading into Friday’s $2.1 trillion options expiration.

The monthly event, known as OpEx, has a reputation for stoking volatility as traders and dealers rebalance their big exposures en masse. Now, with demand for both bullish and bearish index contracts booming while hedging in single stocks explodes in popularity, OpEx comes at a precarious time.

Twice this week, the S&P 500 has briefly surpassed 4,000 -- a battleground threshold for traders that has garnering the highest open interest among contracts set to roll out on Friday. The benchmark gauge has fallen in three of the past four sessions, after jumping more than 5% last Thursday on promising inflation data that sparked a wave of short covering and call buying. The index fell 0.3% to close at 3,947 Thursday.

Amateurs and professionals have been flocking to short-dated contracts to cope with the market whiplash of late, an activity that has exerted outsize impact on the underlying equities. That suggests Friday’s options runoff may expose stocks to further price swings.

Not everyone buys into the idea that derivatives wield this kind of power. But to some market watchers, it’s no coincidence that the OpEx week has seen stocks falling in eight out of the last 10 months.

“Option prices and tails have dropped sharply and present a good opportunity” to add protective hedges, said RBC Capital Markets’ strategist Amy Wu Silverman, citing the possibility that entrenched inflation renews pressure on equities.

Federal Reserve-induced market gyrations are encouraging investors to go all-in on options to place bullish and bearish bets alike. About 46 million options contracts have changed hands each day in November, poised for the busiest month on record, data compiled by Bloomberg show. That’s up 12% from last month.

The boom was in part driven by derivatives maturing within 24 hours. Such contracts made up a whopping 44% of S&P 500 options trading in the past month, according to an estimate by Goldman Sachs Group Inc. strategists including Rocky Fishman.

At the same time hedging activity in single stocks just exploded. The Cboe equity put-call ratio on Wednesday soared to the highest level since 1997. From earnings blowups at tech giants to the uncertain path of the Federal Reserve’s monetary policy, volatility has been the only certainty in the market.

Still, nothing is ever simple in this corner of Wall Street given mixed signals on investor positioning to glean sentiment. For example, judging by the S&P 500’s skew -- the relative cost of puts versus calls that has hovered near multiyear lows -- traders appear more sanguine.

And thanks to the short shelf-life of options that are currently in demand, open interest in S&P 500 contracts has increased at a much slower pace, rising only 4% from the day before the last OpEx. Though with 20 million contracts outstanding, the open interest was the highest since March 2020.

“We did see a lot of recent interest by call buyers and short-covering,” said Steve Sosnick, chief strategist at Interactive Brokers LLC. “One can argue that leaves us a bit more exposed to a down move, but the mood generally remains hopeful. That’s why Fed governors feel the need to continually remind us of their resolve to fight inflation.”

While it’s not easy to get a clear picture about investor positioning in options, dislocations create opportunities for traders.

Easing interest rate volatility will help the equity market stay contained, according to Goldman’s Fishman. He recommends buying puts on Cboe Volatility Index, or VIX, to bet on potential calm into the yearend. The Cboe VVIX Index, a measure of the cost of VIX options, sat below its 20th percentile of a range in the last decade, an indication of attractive pricing, per Fishman.

“Low skew and vol-of-vol point to diminished concern about tail risk,” he wrote in a note.