Challenges Faced by Jeff Bezos: Obstacles and Turning Points

Resilience and perseverance in the journey of Jeff Bezos. A timeline of obstacles and growth.

Jeff Bezos is an American businessman renowned as the founder, executive chairman, and former CEO of Amazon, a leading e-commerce and cloud computing giant. With a net worth exceeding $220 billion as of May 2025, Bezos holds the position of the third-wealthiest individual globally, according to Forbes. He previously held the title of the world's richest person from 2017 to 2021, as recognized by both Forbes and the Bloomberg Billionaires Index.

Sections (6)

Full Timeline Early Life & Education Career & Achievements Success & Recognition Challenges & Struggles Controversies & Scandals

2000: Cash Balance Dips to $350 Million

By the end of 2000, Bezos borrowed $2 billion from banks, as its cash balances dipped to only $350 million.

March 2003: Helicopter crash in West Texas

In March 2003, Jeff Bezos was a passenger in a helicopter that crashed in West Texas while surveying land to buy for Blue Origin; he sustained only minor injuries and was discharged from a local hospital the same day.

2008: Net worth decreasing

After the 2008 financial crisis and Great Recession, Bezos's net worth decreased to $6.8 billion—a 17.7% drop.

September 2011: Blue Origin Prototype Crash

In September 2011, Blue Origin experienced a setback when one of its uncrewed prototype vehicles crashed during a short-hop test flight. Despite the crash, progress in advancing spaceflight since the company's founding was noted.

May 2014: Named "World's Worst Boss"

In May 2014, the International Trade Union Confederation named Jeff Bezos the "World's Worst Boss", citing the inhumanity of employers promoting the North American corporate model.

July 2018: Called to Detail Rekognition Applications

During July 2018, a number of members of the U.S. Congress called on Bezos to detail the applications of Amazon's face recognition software, Rekognition.

September 2018: Introduction of Stop BEZOS Act

In September 2018, Senator Bernie Sanders introduced the Stop Bad Employers by Zeroing Out Subsidies (Stop BEZOS) Act and accused Amazon of receiving corporate welfare.

January 2019: Announced divorce from MacKenzie

In January 2019, Jeff Bezos and his wife MacKenzie released a joint statement revealing that they would be getting divorced after 25 years together.

February 7, 2019: Accused American Media, Inc. of extortion and blackmail

On February 7, 2019, Jeff Bezos published an online essay in which he accused American Media, Inc. owner David Pecker of "extortion and blackmail" for threatening to publish intimate photos of Bezos and current girlfriend Lauren Sánchez.

November 2019: Amazon filed lawsuit over JEDI contract

In November 2019, after the JEDI contract was awarded to Microsoft instead, Amazon filed a lawsuit with allegations that the bidding process was biased.

2019: Harvard Business Review Ranking Drop

In 2019, Harvard Business Review, after ranking Jeff Bezos as the best-performing CEO for 4 years in a row since 2014, did not rank him even in the top 100, due to Amazon's relatively low ESG scores, reflecting risks created by working conditions, employment policies, data security, and antitrust issues.

2019: Wealth reduced by divorce

In 2019, Jeff Bezos's wealth was reduced by the divorce from his wife MacKenzie Bezos. She eventually received 25% of Bezos's Amazon shares, then valued at approximately $36 billion, making her the third-richest woman in the world.

July 6, 2021: Pentagon cancelled the JEDI contract with Microsoft

On July 6, 2021, the Pentagon cancelled the JEDI contract with Microsoft, citing that "due to evolving requirements, increased cloud conversancy, and industry advances, the JEDI Cloud contract no longer meets its needs."