Rise to Success: Career Highlights of Bill Simmons

How Bill Simmons built a successful career. Explore key moments that defined the journey.

Bill Simmons is a prominent American sports writer, podcaster, and cultural commentator. He gained notoriety as "The Boston Sports Guy" before joining ESPN in 2001. During his time at ESPN, he wrote for ESPN.com, hosted "The B.S. Report" podcast, and served as an NBA analyst on "NBA Countdown". In 2015, he left ESPN and subsequently founded The Ringer, a sports and pop culture website, where he currently serves as CEO.

Sections (3)

Full Timeline Career & Achievements Controversies & Scandals

1997: Starts the web site BostonSportsGuy.com

In 1997, Bill Simmons started the website BostonSportsGuy.com while working as a bartender and waiter at night after being unable to get a newspaper job. He also began writing a column for Digital City Boston of AOL.

November 1998: Website Available on the Web

In November 1998, Bill Simmons' website, "Boston Sports Guy", became available on the web. Prior to this, the column was only available on AOL, and Simmons forwarded the column to his friends.

2001: Website's Popularity in 2001

By 2001, Bill Simmons' website averaged 10,000 readers and 45,000 hits per day.

2001: Joins ESPN

In 2001, Bill Simmons joined ESPN to write three guest columns after gaining fame as "The Boston Sports Guy." His second column became one of the most emailed articles on the site that year.

2002: Starts Writing for ESPN The Magazine

In 2002, Bill Simmons began writing a bi-weekly 800-word column for ESPN The Magazine.

2002: Joins Jimmy Kimmel Live! as Writer

In the summer of 2002, Jimmy Kimmel convinced Bill Simmons to write for his new late-night talk show, which premiered after Super Bowl XXXVII.

April 2003: Starts Working on Jimmy Kimmel Live!

In April 2003, Bill Simmons began working as a comedy writer for Jimmy Kimmel Live!.

2004: Online Cartoon Debacle

In late 2004, ESPN launched an online cartoon based on Bill Simmons' columns, which Simmons later called a "debacle" and decided to stop.

2004: Leaves Jimmy Kimmel Live!

In the spring of 2004, Bill Simmons left Jimmy Kimmel Live! after a year and a half to focus full-time on his column but remained in California.

October 1, 2005: Release of "Now I Can Die in Peace"

On October 1, 2005, Bill Simmons released his first New York Times best-selling book, "Now I Can Die in Peace," a collection of his columns leading up to the 2004 World Series victory by the Boston Red Sox.

Now I Can Die in Peace: How The Sports Guy Found Salvation Thanks to the World Champion (Twice!) Red Sox

Check it on Amazon

2005: Column Readership in 2005

In 2005, Bill Simmons' column averaged 500,000 unique visitors a month, according to ESPN.

May 8, 2007: Starts Eye of the Sportsguy Podcast

On May 8, 2007, Bill Simmons began a podcast for ESPN.com called "Eye of the Sportsguy."

June 14, 2007: Podcast Renamed The B.S. Report

On June 14, 2007, Bill Simmons' podcast was changed to "The B.S. Report" with a new theme song written by Ronald Jenkees.

October 2007: Joins E:60 as Special Contributor

In October 2007, Bill Simmons joined the television series E:60 as a special contributor.

2007: Conceives 30 for 30

In 2007, Bill Simmons and Connor Schell conceived the idea for 30 for 30, a series of documentaries commemorating the 30th year of the "ESPN era."

May 2008: Dispute with ESPN Management

In May 2008, Bill Simmons was involved in a dispute with management at ESPN.com. He indicated that he was writing less because he believed that he and ESPN had come to an agreement on creative lines, media criticism rules, and column promotion, but that these agreements had changed within a few months.

July 2008: Simmons Takes Leave to Write Book

In July 2008, Bill Simmons announced that he would take 10 weeks off from writing columns for ESPN.com's Page 2 to concentrate on finishing his second book.

November 2008: Simmons Quits The B.S. Report

In November 2008, Bill Simmons reportedly quit the B.S. Report due to corporate interference with his writing, related to the admission of a pornstar into an ESPN fantasy basketball league.

November 25, 2008: Return to Recording B.S. Report

On November 25, 2008, Bill Simmons returned to recording his B.S. Report podcast with a disclaimer stating, "The BS Report is a free flowing conversation that occasionally touches on mature subjects."

July 27, 2009: Retires from ESPN The Magazine

On July 27, 2009, Bill Simmons announced his retirement from ESPN The Magazine but continued to write for the Page 2 website.

October 6, 2009: 30 for 30 Series Premieres

On October 6, 2009, the "30 for 30" documentary series, co-conceived by Bill Simmons, premiered with "King's Ransom" directed by Peter Berg.

October 27, 2009: Release of "The Book of Basketball: The NBA According to the Sports Guy"

On October 27, 2009, Bill Simmons released his second book, "The Book of Basketball: The NBA According to the Sports Guy". The book, which attempts to identify the best players and teams in NBA history and answer some of the sport's biggest "What ifs?", debuted at the top of The New York Times Best Seller list for non-fiction books.

The Book of Basketball: The NBA According to The Sports Guy

Check it on Amazon

November 2009: Column Readership in November 2009

Between June and November 2009, Bill Simmons' column averaged 1.4 million page views and 460,000 unique visitors a month, according to comScore.

2009: The B.S. Report Popularity in 2009

In 2009, Bill Simmons' podcast, "The B.S. Report", was downloaded more than 25.4 million times.

2009: Punished for Tweets Critical of WEEI

In late 2009, Bill Simmons was punished by ESPN for writing tweets critical of Boston sports radio station WEEI's The Big Show. He was suspended for two weeks from Twitter, but was still allowed to post tweets about his ongoing book tour.

2009: Moderator at MIT Sloan Sports Analytics Conference

Since 2009, Bill Simmons has been a moderator and panelist at the annual MIT Sloan Sports Analytics Conference.

May 2010: New Contract Agreement with ESPN

In May 2010, it was reported that Bill Simmons and ESPN came to an agreement on a new contract, although no official announcement was made on the terms.

2010: Working on Top Secret Editorial Project

Sports blog Deadspin reported in 2010 that Bill Simmons was working on a "top secret editorial project," which would later be revealed as the launch of Grantland.

June 8, 2011: Grantland Launches

On June 8, 2011, Grantland, a sports and pop culture website owned by ESPN, launched with Bill Simmons as editor-in-chief.

2012: Joins NBA Countdown

Starting in the 2012-2013 NBA season, Bill Simmons joined the NBA Countdown pregame show as a panelist/contributor during ESPN/ABC's coverage of the NBA.

March 2013: Suspended from Twitter Again

In March 2013, ESPN again suspended Bill Simmons from Twitter after he posted tweets critical of ESPN's First Take.

2013: Joins NBA Countdown

Bill Simmons joined the NBA Countdown pregame show as a panelist/contributor during ESPN/ABC's coverage of the NBA, starting in the 2012-2013 NBA season.

August 2014: Leaving NBA Countdown to Produce Grantland Basketball Show

In August 2014, ESPN announced that Bill Simmons would be leaving NBA Countdown to produce an 18 episode primetime show for ESPN through Grantland, called The Grantland Basketball Show.

September 24, 2014: Suspended for Criticizing Roger Goodell

On September 24, 2014, ESPN suspended Bill Simmons for three weeks for criticizing NFL commissioner Roger Goodell's handling of the Ray Rice domestic violence case. Simmons stated that Goodell was lying about not knowing the content of the tape showing Rice punching his fiancé.

October 21, 2014: Debut of The Grantland Basketball Hour

On October 21, 2014, The Grantland Basketball Show, later renamed The Grantland Basketball Hour, debuted with Bill Simmons discussing NBA-related current events.

2014: Leaves NBA Countdown

Bill Simmons left the NBA Countdown pregame show prior to the 2014–2015 season.

May 8, 2015: ESPN Announces Contract Non-Renewal

On May 8, 2015, ESPN announced that Bill Simmons' contract, which was due to expire in September 2015, would not be renewed.

July 22, 2015: Signs Multi-Platform Deal with HBO

On July 22, 2015, Bill Simmons announced he had signed a new multi-platform deal with HBO starting in October 2015.

September 2015: End of ESPN Contract

Bill Simmons' contract with ESPN expired in September 2015 and was not renewed.

September 2015: Simmons' Contract Not Renewed by ESPN

In September 2015, ESPN president John Skipper announced that the sports media conglomerate would not be renewing Bill Simmons's contract. It was announced that Simmons would no longer be working at ESPN, effective immediately.

October 2015: Starts HBO deal

In October 2015, Bill Simmons started his new multi-platform deal with HBO.

October 30, 2015: ESPN Shuts Down Grantland

On October 30, 2015, months after deciding not to renew its contract with Bill Simmons, ESPN shut down the Grantland website.

2015: Leaves NBA Countdown

Bill Simmons left the NBA Countdown pregame show prior to the 2014–2015 season.

2015: Bill Simmons Media Group Launched

In the fall of 2015, Bill Simmons launched his venture, the Bill Simmons Media Group, which includes several podcasts and The Ringer website.

February 17, 2016: Announces The Ringer Website

On February 17, 2016, Bill Simmons announced the launch of his new website, The Ringer, as part of his venture, the Bill Simmons Media Group.

June 1, 2016: The Ringer Goes Live

On June 1, 2016, The Ringer website went live, featuring writers and podcasts focusing on sports, pop culture, and technology.

June 22, 2016: Any Given Wednesday Premieres on HBO

On June 22, 2016, Bill Simmons' weekly talk show, Any Given Wednesday, premiered on HBO.

Loading Video...

November 2016: Any Given Wednesday Cancelled

In November 2016, Any Given Wednesday was cancelled by HBO after one season. However, Bill Simmons' multimedia deal with the network continued.

Loading Video...

2016: Founds The Ringer and hosts Any Given Wednesday with Bill Simmons on HBO

In 2016, Bill Simmons founded The Ringer, a sports and pop culture website and podcast network, and became its CEO. He also hosted "Any Given Wednesday with Bill Simmons" on HBO for one season.

May 30, 2017: Vox Media Deal

On May 30, 2017, Vox Media announced that it had entered into a deal to provide advertising sales and access to its publishing platform to The Ringer as part of a revenue-sharing agreement. Simmons retained editorial control of the website.

April 10, 2018: André the Giant Documentary Aired

On April 10, 2018, a documentary on André the Giant, co-produced by HBO Sports, the WWE, and the Bill Simmons Media Group, aired on HBO.

July 2018: HBO Renews Simmons' Contract

In late July 2018, it was revealed that HBO decided to renew Bill Simmons' contract to remain with the network moving forward.

February 5, 2020: Spotify Acquires The Ringer

On February 5, 2020, Bill Simmons announced that Spotify was buying The Ringer for approximately $200 million. The Ringer maintains editorial independence.

May 24, 2022: Simmons Hosts Jalen Green on Podcast

On May 24, 2022, Bill Simmons hosted Jalen Green as a guest on his podcast, where the two discussed the controversy from April 26, 2022 and cleared the air.