Amazon Has Badly Underperformed the S&P 500 and Nasdaq-100 Since Jeff Bezos Stepped Down as CEO. Could Apple Do the Same Starting Sept. 1 When Tim Cook Steps Down?

Since Jeff Bezos stepped down as chief executive officer in mid-2021, Amazon's stock has lagged behind broader market benchmarks. AMZN has delivered a roughly 50% total return over the period, significantly trailing the Nasdaq-100's advance of more than 100% and the S&P 500's approximate 90% gain. The underperformance is largely attributed to the company's massive size, with a market capitalization reaching $2.8 trillion, and substantial capital expenditures required to maintain leadership in cloud and artificial intelligence infrastructure, including an estimated $220 billion investment in 2026. The article compares Amazon's post-transition performance to Apple as Tim Cook prepares to step down as CEO on September 1. While Apple has taken a more conservative approach toward direct AI hyperscaler infrastructure spending—focusing instead on device-level integration—it faces strategic risks if competitors outpace its technological evolution. Overall, market leadership and relative performance in Big Tech will increasingly hinge on the returns generated from substantial AI capital commitments rather than executive leadership shifts alone.