Challenges in the Life of Mike Tyson in a Detailed Timeline

Resilience and perseverance in the journey of Mike Tyson. A timeline of obstacles and growth.

Mike Tyson, nicknamed "Iron Mike," is a former American professional boxer who competed from 1985 to 2024. He is considered one of the greatest heavyweight boxers ever, reigning as the undisputed world heavyweight champion from 1987 to 1990.

Sections (7)

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

1984: Amateur Losses to Henry Tillman

In 1984, Mike Tyson experienced amateur losses to Henry Tillman.

1988: Parted with Manager Bill Cayton and Trainer Kevin Rooney

In late 1988, Mike Tyson parted ways with his manager Bill Cayton and fired his longtime trainer Kevin Rooney, which critics alleged led to a decline in Tyson's boxing skills.

1989: Accusation by Erinn Cosby

In 1989, Erinn Cosby, daughter of Bill Cosby, publicly accused Mike Tyson of sexually assaulting her, though no charges were filed.

February 11, 1990: Loss to Buster Douglas

On February 11, 1990, Mike Tyson lost his undisputed championship title to Buster Douglas in Tokyo. Despite being a heavy favorite with 42/1 odds, Tyson struggled against Douglas's jab and ultimately lost by knockout in the tenth round. After the fight, Tyson's camp complained about the slow count given to Douglas after Tyson knocked him down in the eighth round.

1990: Loss to Buster Douglas

In 1990, Mike Tyson lost the undisputed heavyweight championship to Buster Douglas in what was considered one of boxing's biggest upsets.

1990: Reign as Champion Ends

In 1990, Tyson's reign as the undisputed world heavyweight champion came to an end.

July 1991: Arrest for Rape

In July 1991, Mike Tyson was arrested for the rape of Desiree Washington at the Canterbury Hotel in Indianapolis and charged with multiple offenses.

February 10, 1992: Conviction on Rape Charges

On February 10, 1992, Mike Tyson was convicted on rape charges.

March 26, 1992: Sentencing for Rape Conviction

On March 26, 1992, Mike Tyson was sentenced to six years in prison and four years of probation for rape.

April 1992: Assignment to Indiana Youth Center

In April 1992, Mike Tyson was assigned to the Indiana Youth Center following his sentencing.

1992: Required to Register as Sex Offender

Due to his conviction, in 1992, Mike Tyson was required to register as a Tier II sex offender under federal law.

1992: Conviction and Imprisonment

In 1992, Mike Tyson was convicted of rape and sentenced to six years in prison.

March 1995: Release from Prison

In March 1995, Mike Tyson was released from prison after serving less than three years of his sentence. During this time he got tattoos of Arthur Ashe, Mao Zedong, and Che Guevara.

November 9, 1996: Loss to Evander Holyfield

On November 9, 1996, Mike Tyson fought Evander Holyfield in Las Vegas and lost by TKO in the eleventh round. Holyfield's victory was controversial due to allegations of frequent headbutts during the fight.

July 9, 1997: Boxing License Rescinded

On July 9, 1997, the Nevada Athletic Commission rescinded Mike Tyson's boxing license, fined him US$3 million, and ordered him to pay legal costs due to the ear-biting incident in the Holyfield fight.

February 5, 1999: Sentenced for Assault

On February 5, 1999, Mike Tyson was sentenced to a year in prison, fined $5,000, and ordered to serve two years probation and 200 hours of community service for assaulting two motorists following a traffic accident.

2002: World Heavyweight Title Fight Loss

In 2002, Mike Tyson fought Lennox Lewis for the world heavyweight title but lost by knockout.

August 2003: Filing for Bankruptcy

In August 2003, Mike Tyson filed for bankruptcy after years of financial struggles, despite earning over $300 million during his career. He reportedly had approximately $23 million in debt.

July 30, 2004: Loss to Danny Williams

On July 30, 2004, Mike Tyson faced Danny Williams, dominating the first two rounds, but ultimately lost by knockout in the fourth round after Williams landed powerful punches. Tyson's manager later stated Tyson tore a knee ligament in the first round, impacting his performance.

June 3, 2005: Interview with USA Today

In an interview with USA Today published on June 3, 2005, Mike Tyson expressed feeling like a failure and wanting to escape his life, expressing a desire to become a missionary. He then started tending to pigeons.

June 11, 2005: Tyson Quits Against Kevin McBride

On June 11, 2005, Mike Tyson quit before the seventh round in a fight against Kevin McBride, later admitting he fought for a payday and lacked passion for boxing.

December 29, 2006: Arrest in Scottsdale, Arizona

On December 29, 2006, Mike Tyson was arrested in Scottsdale, Arizona, on suspicion of DUI and felony drug possession after nearly crashing into a police SUV. He admitted to using drugs and stated he was an addict.

2006: Exhibition Bout Against Corey Sanders

In 2006, Mike Tyson returned to the ring for a four-round exhibition bout against Corey Sanders in Youngstown, Ohio, to pay off debts. The bout was poorly received and the tour was canceled.

January 22, 2007: Not Guilty Plea to Drug Charges

On January 22, 2007, Mike Tyson pleaded not guilty in Maricopa County Superior Court to felony drug possession, paraphernalia possession, and two misdemeanor counts of driving under the influence of drugs.

August 2007: Guilty Plea for Drug Possession and DUI

In August 2007, Mike Tyson pleaded guilty in an Arizona court to drug possession and driving under the influence, stemming from a December arrest where he admitted to using cocaine and being addicted.

September 24, 2007: Guilty Plea to Drug Charges

On September 24, 2007, Mike Tyson pleaded guilty to possession of cocaine and driving under the influence.

November 2007: Conviction and Sentencing

In November 2007, Mike Tyson was convicted of possession of cocaine and driving under the influence. He was sentenced to 24 hours in jail, three years' probation, and 360 hours of community service.

May 25, 2009: Daughter Exodus Found Unconscious

On May 25, 2009, Mike Tyson's four-year-old daughter, Exodus, was found unconscious by her brother, tangled in a cord dangling from an exercise treadmill.

May 26, 2009: Death of Daughter Exodus

On May 26, 2009, Mike Tyson's daughter, Exodus, died from injuries sustained after being found tangled in a cord from an exercise treadmill the previous day.

November 11, 2009: Airport Scuffle Arrest

On November 11, 2009, Mike Tyson was arrested after getting into a scuffle with a photographer at Los Angeles International Airport. No charges were filed.

August 2013: Admission of Alcoholism Relapse

In August 2013, Mike Tyson publicly admitted that he had lied about his sobriety and was on the verge of death from alcoholism.

2013: Admission of Using Wife's Urine for Doping Tests

In 2013, Mike Tyson admitted in his autobiography that he used his then-wife Monica Turner's urine to pass doping tests.

May 26, 2024: Tyson Suffers Ulcer Flare-Up

On May 26, 2024, Mike Tyson suffered an ulcer flare-up aboard a plane.

May 31, 2024: Tyson-Paul Fight Postponed

On May 31, 2024, the fight between Mike Tyson and Jake Paul was postponed due to medical advice from Tyson's doctor following his ulcer flare-up.

November 2024: Bout against Jake Paul

In November 2024, Mike Tyson lost against Jake Paul via unanimous decision, at their bout. Despite losing, it became the biggest boxing gate in US history outside of Las Vegas.