Wall Street's Bull Market Is Knocking on the Door of Unwanted History

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Last week was eventful for Wall Street, to say the least. On Monday, Jan. 20, Donald Trump became only the second president to serve two nonconsecutive terms. During President Trump's first term in the White House (Jan. 20, 2017-Jan. 20, 2021), the iconic Dow Jones Industrial Average (DJINDICES: ^DJI), widely followed S&P 500 (SNPINDEX: ^GSPC), and growth-dependent Nasdaq Composite (NASDAQINDEX: ^IXIC) surged by 57%, 70%, and 142%, respectively.

On Tuesday, Jan. 21, the joint venture known as Stargate was unveiled, which will feature $500 billion in investments (spread over four years) to build out the necessary infrastructure to accommodate the rise of artificial intelligence (AI) in America.

But perhaps the crème de la crème is the benchmark S&P 500 ending Jan. 23 at a fresh record-closing high of nearly 6,119. For context, the S&P 500 erased a roughly 5% pullback from its previous high in just a little over one week.

While this is the type of history investors love to see Wall Street make, the current bull market is also knocking on the door of something that's been historically troublesome.

A twenty-dollar bill paper airplane that's crashed and crumpled into a financial newspaper.
Image source: Getty Images.

Wall Street is pushing stock valuation boundaries to the limit

While most economists have been focused on the probability of a U.S. recession taking shape, a record-breaking yield-curve inversion, and the first notable decline in U.S. M2 money supply since the Great Depression, the stock market has, quietly, pushed itself to a valuation premium that's only been witnessed a few times before.

Before digging any deeper, let's state the obvious: Valuation is subjective. Depending on your risk tolerance, investment horizon, and area(s) of focus, what one investor considers to be pricey might be viewed as a bargain by another.

With this being said, Wall Street's bull market is on the cusp of unwanted history.

Arguably, the best valuation tool that allows for the clearest apples-to-apples comparisons is the S&P 500's Shiller price-to-earnings (P/E) ratio. You'll also find the Shiller P/E referred to as the cyclically adjusted P/E ratio (CAPE ratio).

Unlike the traditional P/E ratio, which is limited to just trailing-12-month earnings per share (EPS), the Shiller P/E is based on average inflation-adjusted EPS over the prior decade. Adjusting for 10 years' worth of earnings history ensures that wild vacillations in EPS can't skew the measurement.

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

When the closing bell tolled on Jan. 23, the S&P 500's Shiller P/E ended at 38.59, just shy of its closing high in December 2024 of 38.89. More importantly, this valuation tool is knocking on the door of topping 39 for only the third time in history, when back-tested to January 1871. The other times include a reading of 40 during the first week of January 2022, and the all-time high of 44.19 in December 1999.