Apple Inc. Chief Executive Tim Cook is doing exactly what Albert Einstein said defined insanity—doing the same thing over and over again and expecting different results, according to analyst Trip Chowdhry at Global Equities Research.

In a conference call with analysts last week following Apple’s disappointing fiscal first-quarter results, Chief Financial Officer Luca Maestri said the company plans to be “very active in the U.S. and international debt markets in 2016 in order to fund our capital return activities,” according to a transcript provided by FactSet. Those “activities” will be detailed when second-quarter results are reported in April, Maestri said.

Given how badly the stock AAPL, -1.59% has performed relative to the broader market since the company started raising debt to pay out dividends and make share repurchases, Chowdhry suggests it would seem crazy that Maestri and Cook continue to make the same mistake. Read more about Apple’s true cash position.

FactSet

Cook’s regime began in August 2011. A year later, succumbing to pressure from major shareholders like billionaire activist investor Carl Icahn, Apple paid out its first regular dividend in nearly 17 years on Aug. 16, 2012.

Since then, Apple’s stock has gained 7.1% through Friday, while the S&P 500 SPX, -0.84% has climbed 37% and the Nasdaq Composite COMP, -1.26% has run up 51%. During the same time, Chowdhry points out that Apple has spent $110 billion on share buybacks, $43 billion on dividends and debt has skyrocketed to $63 billion.

“Obviously, share buybacks and dividends are not working,” Chowdhry wrote in a note to clients. “And somehow the current CFO thinks that doing the same thing over and over again may generate different results.”

Don’t miss:Apple, Cisco and IBM prove that stock buybacks are a sham.

What might be more concerning than simple price underperformance is how depressed Apple’s valuation has become, relative to the broader market.

Apple’s price-to-earnings ratio (last 12 months of earnings) has sunk to 10.33 as of Friday from 15.52 on Aug. 16, 2012, according to FactSet data. Over the same time, the P/E ratio for the S&P 500 has increased to 16.64 from 13.25.

FactSet

Chowdhry calculates that the potential shareholder value lost from the decline in Apple’s P/E multiple relative to the S&P 500’s is about $480 billion.

“Apple share buybacks have been a complete disaster,” Chowdhry wrote.

The analyst compared Cook to John Sculley, Apple CEO from 1983 to 1993, who Chowdhry says was “instrumental in destroying Apple, and evaporating cash from the balance sheet.” Apple started paying its first dividend under Sculley’s reign in May 1987.

From the end of 1982 through the end of 1993, Apple’s stock nearly doubled, but both the S&P 500 and Nasdaq Composite more than tripled.

FactSet

One person who may be pushing for Cook to keep doing the same thing is Icahn, who owned 52.8 million Apple shares as of Sept. 30, according to the latest regulatory filings.

If he still owns that amount through Feb. 8, Apple will cut him a check for $27.44 million on Feb. 11, for the regular quarterly dividend of 52 cents a share.