CAT Bearish Calendar Put Spread with 445% Upside

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This CAT Calendar Put Spread Targets 445% Return

Bearish play with a target stock price of $260

Strategy has +445% upside potential and 13% undervalued

Strategy: Long CAT Calendar Put Spread
Sell 17-Nov-23 260 Put5.20
Buy 15-Dec-23 260 Put6.90

Caterpillar is weaker by -0.5% today to $279.64. The price action today indicates stock and market weakness. Setting up this calendar spread with strikes at $260 gives you a bearish bias to tap into CAT stock's weakness.

Option Profit Calculator Results for CAT Calendar Spread at 17-Nov-23 Expiration

In this scenario, the optimal stock price for the option strategy would be $260.00 on the date of the first expiration, November 17, 2023. This is equal to the strike price of the options in the spread. Since there is notable downward pressure in both the market and CAT, and the strikes are below the current stock price of $279.12, the spread is taking advantage of the market's bearish bias. If the stock price is $260.00 at expiration, we can benefit from the 17-Nov-23 put, which we sold, expiring worthless, and the option that we are long, the 15-Dec-23 put, will still have time premium built in.

Since we do now know what the exact implied volatility will be on November 17, we can use our historical data to make an educated estimate to help us calculate the value of the 15-Dec-23 option. Applying the median historical implied volatility of 31.8 from similar options, the theoretical value of the put is 9.26 at the date of the 17-Nov-23 expiration. Using the above assumptions gives us a potential upside of +445% for this calendar spread.

CAT Calendar Spread Value vs. Market Price

According to Market Chameleon estimated value, CAT Calendar Spread is trading at a 13% discount to historical benchmark.

If we use historical data to measure how similar spreads in CAT were priced in the market, the 4-year average price was 1.96, with a high mark of 2.13 and a low of 1.75.

Currently, the calendar put spread is bid at 1.40 and offered at 1.70. The midpoint of the spread is 1.55.

If we use 1.96 as our historical fair value benchmark, the current market ask price is at a 13% discount, while the current market midpoint represents a 21% discount.

Current PriceHistorical Values of Similar Spreads
Market Chameleon captures daily records of market data to calculate historical benchmarks and generate estimated values.


The CAT calendar put spread we've identified here can be a good way to play a bearish outlook because the option strategy has a +445% upside potential, is 13% underpriced relative to historical measures, and will benefit from the stock price moving lower to $260.

See how Market Chameleon can help you make smarter and more efficient trades!

NOTE: Stock and option trading involves risk that may not be suitable for all investors. Examples contained within this report are simulated And may have limitations. Average returns and occurrences are calculated from snapshots of market mid-point prices And were Not actually executed, so they do not reflect actual trades, fees, or execution costs. This report is for informational purposes only, and is not intended to be a recommendation to buy or sell any security. Neither Market Chameleon nor any other party makes warranties regarding results from its usage. Past performance does not guarantee future results. Please consult a financial advisor before executing any trades. You can read more about option risks and characteristics at

The information is provided for informational purposes only and should not be construed as investment advice. All stock price information is provided and transmitted as received from independent third-party data sources. The Information should only be used as a starting point for doing additional independent research in order to allow you to form your own opinion regarding investments and trading strategies. The Company does not guarantee the accuracy, completeness or timeliness of the Information.