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 and former CEO of Amazon, a global e-commerce and cloud computing giant. As of December 2025, his net worth is estimated at $239.4 billion, ranking him as the fourth richest person globally. He held the title of the wealthiest person in the world from 2017 to 2021.

Sections (6)

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

2002: Amazon Web Services Launched and Workforce Reduction

In 2002, Bezos led Amazon to launch Amazon Web Services. Revenues stagnated later that year, and after the company nearly went bankrupt, he closed distribution centers and laid off 14% of the Amazon workforce.

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. All occupants survived with Bezos sustaining only minor injuries.

2008: Net Worth Decreases After Financial Crisis

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

September 2011: Blue Origin Prototype Vehicle Crashed

In September 2011, one of Blue Origin's uncrewed prototype vehicles crashed during a short-hop test flight, which was viewed as a setback, although the company's progress was noted.

May 2014: Bezos Named "World's Worst Boss"

In May 2014, the International Trade Union Confederation named Jeff Bezos the "World's Worst Boss," criticizing his promotion of the North American corporate model.

2015: Bezos Denounced New York Times Piece

In 2015, Jeff Bezos sent a memo to employees denouncing a New York Times article, exemplifying his tendency to publicly contest claims made in critical articles.

2016: Public Response to Bezos' Philanthropy

Since 2016, Jeff Bezos' relative lack of philanthropy compared to other billionaires has drawn a negative response from the public.

January 2018: Net Worth Increase and Amazon Worker Protests

From January 2017 to January 2018, Jeff Bezos's net worth increased by $33.6 billion. Following a report by Quartz highlighting Bezos' wealth, Amazon workers in Poland, Germany, and Spain participated in demonstrations and labor strikes.

March 2018: Investment in India and Trump's Accusations

In March 2018, Bezos sent Amit Agarwal to India with $5.5 billion to localize operations. Also that month, President Donald Trump accused Amazon and Bezos of sales tax avoidance, postal route misuse, and anti-competitive practices.

May 1, 2018: Alleged Hacking via WhatsApp Message

On May 1, 2018, Forensic analysis indicated that Bezos's mobile phone was likely hacked using a malicious file hidden in a video sent in a WhatsApp message from the personal account of the crown prince.

July 2018: Inquiries About Amazon's Face Recognition Software

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

September 2018: Senator Sanders Introduces Stop BEZOS Act

In September 2018, Senator Bernie Sanders introduced the Stop Bad Employers by Zeroing Out Subsidies (Stop BEZOS) Act, criticizing Amazon for allegedly receiving corporate welfare due to some of its workers relying on food stamps.

2018: Joint Enterprise Defense Infrastructure (JEDI) Project Controversy

In 2018, controversy arose over a $10 billion contract with the Pentagon known as the Joint Enterprise Defense Infrastructure (JEDI) project, which was allegedly written up in a way that favored Amazon.

2018: Washington Post Employees Criticize Bezos

In 2018, more than 400 Washington Post employees wrote an open letter to Jeff Bezos criticizing his poor wages and benefits for his employees.

February 7, 2019: Accusations of Extortion and Blackmail

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

March 2019: Accusation of Saudi Government Hacking

In March 2019, Bezos's security consultant accused the Saudi government of hacking Bezos's phone, linking it to the Washington Post's coverage of Jamal Khashoggi's murder.

November 2019: Amazon Files Lawsuit Over JEDI Contract Award

In November 2019, Amazon filed a lawsuit alleging bias after the JEDI contract was awarded to Microsoft instead.

2019: Harvard Business Review Ranked Bezos Outside Top 100 CEOs

In 2019, Harvard Business Review, after ranking Jeff Bezos the best-performing CEO for four years, did not rank him even in the top 100, citing Amazon's low ESG scores reflecting risks related to working conditions, 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, who received 25% of Bezos's Amazon shares, making her the third-richest woman in the world.

2019: PAC Attempt to Defeat Kshama Sawant

In 2019, a PAC linked to Bezos spent over $1 million in an unsuccessful attempt to defeat the reelection bid of Seattle city council member and activist Kshama Sawant.

January 2020: Report on Timing of Bezos's Phone Hack

In January 2020, The Guardian reported that the hack of Bezos's phone was initiated before the murder of Jamal Khashoggi but after Khashoggi wrote critically about the crown prince in the Washington Post.

July 6, 2021: Pentagon Cancels JEDI Contract

On July 6, 2021, the Pentagon cancelled the JEDI contract with Microsoft, citing evolving requirements and industry advances.

December 2023: Washington Post Employees Strike

Around 750 employees at The Washington Post went on a brief strike in December 2023 in response to Jeff Bezos' plans to lay off staff.

2024: Criticism of Bezos' Ownership of The Washington Post

In 2024, Bezos' ownership of the Washington Post was subject to scrutiny and criticism regarding his treatment of employees as well as his influence on the paper's content.

2024: Bezos Blocks Washington Post Endorsement

In 2024, Jeff Bezos blocked the Washington Post's editorial board from endorsing Kamala Harris in the presidential election, leading to criticism and resignations.

January 2025: Cartoonist Resigns from the Post

In January 2025, editorial cartoonist Ann Telnaes resigned from the Post after it refused to run a satirical cartoon critical of the relationship between American billionaires and President Donald Trump.

February 2025: Opinion Section to Focus on Specific Opinions

In February 2025, Jeff Bezos announced that the opinion section of the Post will give voice only to opinions that support "personal liberties" and "free markets", leading to resignations and subscription cancellations.