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 global leader in e-commerce and cloud computing. As of May 2025, his estimated net worth is $220.9 billion, ranking him as the third-richest person worldwide, after holding the top position from 2017 to 2021.

Sections (6)

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

2000: Kozmo.com Investment and Borrowing

In 2000, Bezos invested in kozmo.com for $60 million and borrowed $2 billion from banks as Amazon's cash balances decreased.

2002: Launch of Amazon Web Services

In 2002, Bezos led Amazon to launch Amazon Web Services, which compiled data from weather channels and website traffic. Revenue stagnated and the company almost went bankrupt.

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 for Blue Origin. All occupants survived, and Bezos sustained minor injuries.

2008: Net worth decrease

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

September 2011: Blue Origin Prototype Vehicle Crash

In September 2011, an uncrewed prototype vehicle from Blue Origin crashed during a short-hop test flight, which was considered a setback despite the company's progress in spaceflight.

May 2014: Named "World's Worst Boss"

In May 2014, the International Trade Union Confederation named Jeff Bezos the "World's Worst Boss".

2015: Denouncing NYT Piece

In 2015, Jeff Bezos sent a memo to employees denouncing a New York Times piece.

2016: Public Criticism

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

March 2018: Investment in India and Trump's Accusations

In March 2018, Bezos dispatched Amit Agarwal to India with $5.5 billion to localize operations. Also, U.S. President Donald Trump accused Amazon and Bezos of tax avoidance and anti-competitive practices.

May 1, 2018: Probable Start of Bezos Phone Hack

On May 1, 2018, forensic analysis concluded it was "highly probable" that the hack of Jeff Bezos's mobile phone was achieved using a malicious file hidden in a video sent via a WhatsApp message from the personal account of the crown prince.

September 2018: 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.

September 2018: Reports on Bezos's Philanthropy and Day 1 Fund

In September 2018, it was reported that Jeff Bezos was the only one of the top five billionaires who had not signed the Giving Pledge, and questions were raised about his new Day 1 Fund's structure and funding.

2018: Controversy Over JEDI Contract

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

2018: Criticism of Employee Wages and Benefits

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

January 2019: Divorce Announcement and Affair Revelation

In January 2019, Jeff Bezos and his wife MacKenzie released a joint statement revealing they would be getting divorced after 25 years together. Subsequently, National Enquirer revealed that Bezos had an affair with Lauren Sánchez.

February 7, 2019: Accusations of Extortion and Blackmail

On February 7, 2019, Jeff Bezos accused American Media, Inc. owner David Pecker of "extortion and blackmail" for threatening to publish intimate photos of him and Lauren Sánchez if he did not stop his investigation into how his text messages and other photos had been leaked to the National Enquirer.

March 2019: Accusations of Saudi Government Hacking Bezos's Phone

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

2019: Harvard Business Review Ranking

In 2019, Harvard Business Review did not rank Jeff Bezos in the top 100 CEOs, citing Amazon's low ESG scores.

2019: Divorce and Wealth Reduction

In 2019, Jeff Bezos's wealth was reduced due to his divorce from MacKenzie Bezos, who received 25% of his Amazon shares, valued at approximately $36 billion.

2019: Expenditure in Seattle City Council Election

In 2019, a PAC linked to Jeff 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 Bezos Phone Hack Initiation

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

July 6, 2021: Pentagon Cancels 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."

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: Controversy Over Washington Post's 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 and cancellations of subscriptions.

January 2025: Cartoonist Resignation from The Washington 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, sparking conversations about the paper's ownership under Bezos.

February 2025: New Opinion Section Direction and Editor's Resignation

In February 2025, Jeff Bezos announced that the opinion section of the Post will only publish opinions supporting "personal liberties" and "free markets", leading to the resignation of opinion editor David Shipley and a significant loss of digital subscribers.