I asked ChatGPT to build a ‘monster dividend’ Stocks and Shares ISA for 2026

Can ChatGPT help sniff out the very best in ‘monster dividends’ for a Stocks and Shares ISA? Our Foolish author sets the large language model a task.

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The tax-free advantages of the Stocks and Shares ISA make it perfect for those hunting top-class dividend stocks. Investors can lose as much as 39% of dividend payments due to tax reasons. But in an ISA, that figure is 0%.

Of course, there is a huge difference between the kind of stocks that pay dividends that increase for years and decades and other kinds that slash theirs at the first sign of trouble.

That’s why I recruited everyone’s favourite incorporeal buddy, ChatGPT. I gave the 21st-century Oracle a simple request: “Build me a Stocks and Shares ISA for 2026 focused on ‘monster dividends’.”

Please note that tax treatment depends on the individual circumstances of each client and may be subject to change in future. The content in this article is provided for information purposes only. It is not intended to be, neither does it constitute, any form of tax advice. Readers are responsible for carrying out their own due diligence and for obtaining professional advice before making any investment decisions.

The answer

ChatGPT’s answer came in three parts:

  • The Monster Yield Core (7%-10%+) — 40%
  • The “Dividend Aristocrats” (reliable growth) — 40%
  • Global Diversification (the ETF route) — 20%

The first 40% of the Stocks and Shares ISA targets those ‘monster’ yields of 7% plus. Stocks it highlighted included some of the FTSE 100‘s biggest hitters like Legal & General and Phoenix Group. The FTSE 250‘s Taylor Wimpey found its way on there too.

Its fourth choice, WPP, raised an eyebrow from me as the advertising firm’s huge yield is on the chopping block. This is a telling reminder that we cannot rely on artificial intelligence as the last word when it comes to financial matters.

The next 40% is composed of long-increasing dividends that are sometimes called ‘Dividend Aristocrats’ or ‘Dividend Knights‘. The snowball effect of compound interest is amplified with stocks like British American Tobacco or National Grid (LSE: NG.) that might ramp up dividends over time – although there is no guarantee that past increases will be the same as future ones.

Monsters under the bed

National Grid is another stock that I believe needs to be looked at with circumspection. On the surface, it has all the makings of a terrific dividend stock that can churn out payments for decades to come.

Managing the UK’s electricity infrastructure (and parts of the US) is going to be important for a long time. Moreover, the firm has a monopoly over the services provided, which makes future incomes about as guaranteed as they come.

But the company is going through a large transition as huge swathes of existing infrastructure need to be worked on or replaced for the shift to green energy. This means large amounts of debt, for one. But the cost and difficulty of building anything in this country these days makes me wonder whether there will be more issues down the road. As such, it’s not one I’d personally buy for a monster dividend.

The last 20% of ChatGPT’s portfolio? That is in dividend ETFs, which are broad managed funds that focus on dividends. These funds contain hundreds of stocks, which can help with diversification but make it hard to get an edge over the average market return.

John Fieldsend has positions in British American Tobacco P.l.c., Legal & General Group Plc, and Phoenix Group Plc. The Motley Fool UK has recommended British American Tobacco P.l.c. and National Grid Plc. Views expressed on the companies mentioned in this article are those of the writer and therefore may differ from the official recommendations we make in our subscription services such as Share Advisor, Hidden Winners and Pro. Here at The Motley Fool we believe that considering a diverse range of insights makes us better investors.

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