June 16, 2026

Ep71 - Cash-Secured Puts: Case Study of TGT Trade

45 minutes

Dan walks listeners through a real-world cash-secured put case study using Target Corp. (TGT) as an example. He demonstrates how to evaluate a trade from start to finish, including technical and fundamental analysis, option selection, trade execution, liquidity considerations, and management planning. The episode emphasizes that successful wheel trading is not just about understanding option mechanics, but about developing a repeatable process for finding, executing and managing high-probability trades.

Key Topics

Understanding the difference between skate objective and trade objective wheel trades

Evaluating assignment risk before entering a cash-secured put position

Using technical support levels to identify high-probability trade setups

Incorporating earnings dates and implied volatility into trade selection

Applying fundamental analysis to strengthen trade candidates

Comparing strike prices and expirations to optimize risk and return

Using the 10% liquidity rule when evaluating option markets

Cash-secured puts vs. put credit spreads and their respective risk profiles

Improving execution through effective option order “middling” techniques

Building and implementing a trade management plan, including profit targets, rolling decisions and exit criteria

Key Takeaways

Every wheel trade should begin with a clearly defined objective: Are you trying to collect premium (skate) or acquire stock (trade)?

Assignment should never be treated as an afterthought; traders should understand and plan for assignment before entering a position.

Strong cash-secured put candidates combine technical support, reasonable fundamentals, elevated implied volatility and sufficient premium.

Earnings events can dramatically change risk profiles and should be factored into expiration selection.

Liquidity matters. Wide bid-ask spreads can impact both execution quality and trade management flexibility.

The best trade is not always the one with the highest premium. Risk, probability and return on capital must all be considered together.

Entering profit-taking orders immediately after opening a position can help systematically remove unproductive risk.

Rolling should only occur when a new trade opportunity stands on its own merits and still offers a valid edge.

Traders should not roll simply to avoid taking a loss; there must be a technical or fundamental rationale supporting the adjustment.

Successful wheel traders think in terms of return on risk and long-term cycles rather than focusing on individual trades in isolation.

Connect

Learn more about host Dan Passarelli and Market Taker Mentoring: MarketTaker.com

Get exclusive content including video trade walk-throughs, Dan's actual trades, monthly AMA webinars and more: wealthbuildingpodcast.com

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Disclosure:

Options involve risk and are not suitable for all investors. Prior to buying or selling an option, investors must read Characteristics and Risks of Standardized Options (ODD), which can be found at https://www.theocc.com/company-information/documents-and-archives/options-disclosure-document

Don’t trade with money you are not prepared to lose. Anything discussed on this show is intended to be generalized information and not intended to be a recommendation to buy or sell any security. The host and guests are not familiar with listeners’ specific situations. For trading information relevant to your specific needs, speak with a licensed broker or advisor.

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By Wealth Building With Options

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