Don Kaufman is options trader and educator. Former CBOE market maker, former Chief Derivatives Instructor at thinkorswim, and former Director of the Trader Group at TD Ameritrade. In 2015 he co-founded TheoTrade to teach traders how volatility, probability, and risk really work.

The Oil Trade That Risks $148 To Make $352

Oil traders are pricing a spike about the same as a crash. Go 42 days out on the oil futures options, with crude around $87 a barrel, and look at the implied volatility, the number that sets the price tag on an option. The higher it is, the more the option costs. A put, which pays off if oil falls, $10 below the market at the $77 strike has an implied volatility of about 47%. A call, which pays off if oil rises, $10 above the market sits at about 47% or 48%. In other words, a bet on a $10 drop and a bet on a $10 jump cost about the same. The gap between those 2 numbers is called skew, and it tells you how much extra traders will pay to protect themselves from a move in one direction. When traders are scared of something, they pay up

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How Big Money Saw Brazil Coming

https://youtu.be/6VSH7pNONXo XP jumped 31% today. Someone bought 50,000 calls on it last Friday. Brandon Chapman caught that print and several others before Brazil exploded. The options market flagged this rally days before the headlines hit. The Brazilian ETF climbed 12.5% today. Brandon ties the move to the Brazilian election, where Flavio Bolsonaro may be expected to finish ahead of Lula da Silva. Petrobras rallied 11.5% on top of it. Brazil was the clear winner across global equities. Brandon found the setup sitting in the options tape over a week ago. Bullish out of the money calls kept hitting EWZ and other Brazilian names near the lows. Those buyers put dealers on the hook. Dealers sold the calls, so a rally forces them to buy stock to hedge. The stocks ran overnight and over the weekend. Dealers had to chase, and the gamma squeeze did the rest. Brandon compares it to

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Why Your Micro S&P Options Only Go 2 Months Out Right Now

The longer expirations on micro S&P options are gone for now. The Chicago Mercantile Exchange is moving its Micro E-mini S&P 500 options to financial settlement. Financially settled means cash settled, so at expiration, there’s no futures contract to deal with. You just get the cash. The new contracts only list short-dated expirations, though, and the longer ones went away. Some of you have emailed me about it, and on some platforms, you can only go out about 53 days right now. Nobody freak out. I’ve talked to CME directly. They’ll add longer expirations back, but it could take 6 to 8 weeks to get them up and running. I asked them, politely, for quarterly expirations, like December, March, June and September. Until then, plan your MES trades around the shorter dates. I can’t re-up some of my longer trades yet either, so I’m waiting right along with you. How

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50,000 Microsoft Calls In 3 Minutes, And What I Did About It

This morning, 50,000 Microsoft calls traded in the first 3 minutes. The wild part is Microsoft did nothing before the bell.  But once the market opened, a call-buying program hit, and within 15 minutes, the stock had already moved as far as the options market expected it to move ALL WEEK.  You’ll see moves like this again, probably this week. Before you touch one, run these 3 checks. First, look at where the options traded. On your platform’s options time and sales, every trade shows whether it went off at the bid, the ask or somewhere in between. This morning, 17,000 of those Microsoft calls traded at the ask or above. That means buyers weren’t negotiating. They were sweeping, buying everything the market makers offered, at any price. When you see that, you’re looking at a program, and programs can stop as fast as they start. Second, measure the move

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S&P 500’s Hidden Bear Market

https://youtu.be/2n1bk7fkBVI The S&P 500 trades just off its record highs. Nearly 60% of its stocks sit in bear market territory. I see about 300 points of upside from here. I see about 800 points of downside. That lopsided setup drove everything I covered in this weekend’s update. I’ll start with the upside. I think the S&P 500 can reach 8,000 by the end of the year, and I’d even argue for 8,100. The downside could turn into an abyss. A drop to the bottom of the volatility box takes the S&P 500 under 7,400. A break of that box opens a straight shot below 7,000. I’m watching the bond market as the trigger. Notes dropped hard about 45 minutes after Friday’s open, and the S&P 500 slid right along with them. Apple recovered enough to steady the tape. That won’t hold forever. Nvidia isn’t bigger than rates, and nothing else

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Why I’m Betting Target Is Next To Fall

Walmart went from up 20% this year to down about 7%. Costco was up 30% on the year, and now it’s up about 6%. Nike just traded at its lowest price in more than a decade, and McDonald’s is sitting in bear market territory. Nobody’s talking about it, but the retailers are getting systematically dismantled. And I think Target is next in line. Why Stocks Rallied On A 29,000-Job Dud Friday’s jobs report was a dud. The economy added just 29,000 jobs in September, and unemployment rose to 4.2%. Wall Street was looking for around 90,000. The analysts who look at jobs reports couldn’t hit the broad side of a barn. The S&Ps rallied anyway, because crappy jobs mean maybe the Fed doesn’t have to hike again. But look at where the rally came from. Nvidia was up almost 3%, and the semiconductors carried the whole thing, while just about

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A Bullish Trade For Bearish Reasons

My favorite trade this week is bullish for bearish reasons. On Friday, I joined Marley Kayden and Rick Ducat on Schwab Network’s Trading 360 for their Big 3, and I laid out 3 trades, with the strikes and expirations for each one. One is a bearish spread on the retailer I think is next to fall, while Walmart and Costco are already getting hit. Another is a bullish bet on a sector that’s been pummeled this year.  I’m only making it because I’m looking for tech to sell off in the next few weeks, and when that happens, I expect the money to rotate somewhere. And then there’s a short-term call spread on one of the biggest names in tech, set up for a gamma squeeze.  In a gamma squeeze, traders pile into calls, the market makers who sold them have to buy stock to hedge, and that buying pushes

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Where Scared Money Goes Next

https://youtu.be/uyl6IPzTNFs The US dollar ran from 101 to 102.14 in a single session. Blake Young points out that a move that size can take a month or more. Blake reads it as foreign capital rushing into the US. He’s already mapping where that money lands next. The SPY whipsawed for more than three hours with single candles covering 25% to 50% of a full day’s range. It sat off just 0.1% when Blake recorded. Blake found the real move in bonds. The 10-year hit its lowest level in years, then reversed to test Monday’s high on volume running above 100% of average. Bonds and the dollar climbing together usually signal fresh capital arriving from overseas. Blake points to the euro sliding from 113.71 to 112.49 as more proof. The dollar index just cleared every resistance level back to early 2025. Blake calls it one of the largest single candle days

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Where The Nasdaq Goes From Here

Gianni Di Poce sees the Nasdaq climbing to 32,000 or even 33,000. He calls that target conservative. This morning’s cooler than expected inflation report pushed stocks to new highs. The fade that followed doesn’t change his view. The data sharply cut the odds of a Fed rate hike at the October meeting. Gianni sees that shift driving the positive reaction. The Nasdaq outperformed on the session. Money rotated out of semiconductors and back into software. Gianni remains very bullish on software. Semiconductors make up 40% of the tech index. Software makes up only around 20%. Microsoft hit new highs today. Palantir, Nvidia, and Google all showed strength too. Gianni’s rule on price action is simple. A consolidation near the highs of a move is bullish. The Nasdaq set a record high just a week ago. It’s now carving out a wedge pattern near that level. A false breakout would have

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I Spent This Week At A Thinkorswim Reunion

I spent this week at a thinkorswim reunion, except it was a Robinhood event. I’m in Houston for Robinhood’s HOOD Summit, and it’s like somebody put the band back together, everybody’s just 20 to 25 years older.  A lot of the people I worked with at thinkorswim and TD Ameritrade now run Robinhood, including Steve Quirk, its chief brokerage officer. Back then, I was the youngest guy by about 15 years. I had to break it to them that I’m 50 now. But the part that surprised me was the clients. About 1,200 of them are here, invitation-only, and they were not what I expected. The average age was probably in the early 40s.  They asked sharp questions, and almost everybody I talked to was deep into technology. It’s the same kind of trader we had on thinkorswim back in the day, maybe a little younger. Robinhood’s presentation Tuesday night

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Don Kaufman Don Kaufman

TheoTrade co-founder, former CBOE market maker and thinkorswim Chief Derivatives Instructor.

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