From political dirty tricks to raucous speeches, Anthony Weiner often courted controversy in his two decades in public office. But in the later years of his political career, Weiner has gone from the talk of the Hill to the talk of the tabloids, unable to kick an ugly habit of sexting other women until he broke the law and was sentenced to prison. It never should’ve been this hard for Weiner.

November 1991 – Weiner wins a newly created Brooklyn seat in the New York City Council. At only 27 years old, he became the council’s youngest ever member at the time.  

Nov. 5, 1998 – Weiner follows in the footsteps of his old boss Chuck Schumer, beating Melinda Katz – in the primary and the general – in a race to replace Schumer in Congress.

Sept. 15, 2005 – In his first election loss, Weiner concedes to Fernando Ferrer in the Democratic primary for New York City mayor.

May 26, 2009 – After teasing a run for months, Weiner declines to run for mayor – which was first reported by City Hall News, City & State’s predecessor publication.

July 10, 2010 – Weiner marries Huma Abedin, a senior aide to then-Secretary of State Hillary Clinton, in a wedding officiated by former President Bill Clinton.

July 29, 2010 – Weiner gets national attention for his fiery House floor berating Republicans for not supporting a 9/11 health care bill.

May 27, 2011 – Troubles arise, as a picture of a man’s bulging underwear appears on Weiner’s Twitter account. Weiner denies it’s him for more than a week.

June 16, 2011 – After admitting the picture was of him and that he had sexted with at least six other women, Weiner resigns from Congress under public pressure.

May 22, 2013 – Hoping for redemption, Weiner announces he’s running for mayor. Despite some distaste from voters, Weiner tops several polls.

July 23, 2013 – Weiner admits he kept sexting women after his resignation. His mayoral campaign falls apart and he ends up in 5th place in the Democratic primary.

Aug. 28, 2016Another story comes out that Weiner has continued to sext other women. Abedin announces the couple is separating.

Sept. 21, 2016 – A 15-year-old girl says that Weiner had sexted her for months, aware of her age. The FBI begins investigating.

Oct. 28, 2016  - FBI Director James Comey publically reopens the investigation into Clinton’s emails after finding new evidence on a laptop seized from Weiner and Abedin. 

Sept. 25, 2017 – A week after his first divorce proceeding, Weiner is sentenced to 21 months in prison for sharing lewd material with a minor.