President Donald Trump Just Made Stock Market History — and It's an Ominous Warning for Investors


Yesterday, Donald Trump took the oath of office and a new era began for Wall Street.

Following his victory in November, the broader market was propelled higher, with financial stocks surging on the prospect of less oversight.

Additionally, many of stock markets most-influential businesses have jumped on the belief that Trump will target another round of corporate income tax rate cuts — at least for businesses that make their products in America. After the Tax Cuts and Jobs Act was signed into law by Trump in December 2017, stock buyback activity for S&P 500 (SNPINDEX: ^GSPC) companies soared.

Donald Trump speaking with reporters from the East Room of the White House.
President Trump addressing reporters. Image source: Official White House Photo by Shealah Craighead, courtesy of the National Archives.

Investors are also excited about the prospect of a repeat performance. During Trump’s first term in the White House, the ageless Dow Jones Industrial Average (DJINDICES: ^DJI), benchmark S&P 500, and growth-powered Nasdaq Composite (NASDAQINDEX: ^IXIC) galloped higher by 57%, 70%, and 142%, respectively.

While Wall Street has been given plenty of reason to be excited about President Donald Trump’s second term, he’s also making ominous stock market history — and it should have investors concerned.

Among the dozens of presidents that have preceded Trump in the Oval Office, none can say they’ve inherited a pricier stock market.

The most common way to measure “value” on Wall Street is with the price-to-earnings (P/E) ratio. The P/E ratio is arrived at by dividing a company’s share price into its trailing-12-month earnings per share (EPS), with a lower P/E ratio typically signifying a better value.

Though the P/E ratio is a fantastic tool for quickly assessing the relative cheapness or priciness of a mature business, it can be easily tripped up by short-term shock events that disrupt corporate earnings. For example, lockdowns during the COVID-19 pandemic in 2020 made trailing-12-month EPS relatively useless for a number of companies.

This is where the S&P 500’s Shiller P/E Ratio comes into play. You’ll commonly find the Shiller P/E Ratio also referred to as the cyclically adjusted P/E Ratio (CAPE Ratio).

S&P 500 Shiller CAPE Ratio Chart
S&P 500 Shiller CAPE Ratio data by YCharts.

The Shiller P/E is based on average inflation-adjusted EPS over the prior 10 years. Using a decade of inflation-adjusted earnings history means that shock events can’t skew this valuation metric. In other words, it provides as close to an apples-to-apples valuation measure as possible when back-tested more than 150 years.

As of the closing bell on Jan. 17, the S&P 500’s Shiller P/E sat at 38.11. This marks the highest reading for an incoming president dating back to January 1871 (i.e., as far back as the Shiller P/E can be back-tested). For context, the average Shiller P/E over the last 154 years is 17.19.



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