Early life

William J. Simmons III was born on September 25, 1969, to William Simmons and Jan Corbo. Simmons was an only child and grew up in Marlboro and Brookline, Massachusetts before moving to Stamford, Connecticut to live with his mother after his parents divorced at the age of 13. His father, William Simmons, was a school administrator, and his stepmother, Molly Clark, is a doctor. Growing up, Simmons wanted to be a columnist for one of the two major newspapers in Boston. He attended The Greenwich Country Day School and then attended Brunswick School in Greenwich, Connecticut for high school. In 1988, he completed a postgraduate year at Choate Rosemary Hall, a prep school located in Wallingford, Connecticut.

Simmons then attended the College of the Holy Cross. While attending he wrote a column for Holy Cross's school paper, The Crusader, called "Ramblings" and later served as the paper's editor. He also re-started the school’s parody newspaper and started a 12-14 page, underground, handwritten, magazine about the people in his freshman hall called "The Velvet Edge." He graduated in 1992 with a B.A. in Political Science. Subsequently, while living in Brookline, Massachusetts, he studied at Boston University where he received his master's degree in print journalism two years later.

Early career

For eight years following grad school, Simmons lived in Charlestown working various jobs before eventually landing a job at ESPN. The September after grad school, Simmons started working at the Boston Herald as a high school sports reporter, mainly "answering phones... organizing food runs, [and] working on the Sunday football scores section." Three years later he got a job as a freelancer for Boston Phoenix but was broke within three months and started bartending. In 1997, unable to get a newspaper job, Simmons "badgered" Digital City Boston of AOL into giving him a column, and he started the award winning web site, BostonSportsGuy.com while working as a bartender and waiter at night. He decided to call his column "Sports Guy" since the site had a "Movie Guy."

Originally the column was only available on AOL, and Simmons forwarded the column to his friends. He began getting email from people asking if he could put them on his mailing list. For the first 18 months, Simmons would send it to about 100 people, until it became available on the web in November 1998. The website quickly built up a national following since so many friends from high school and college all e-mailed it to each other. In the winter of 2000, Simmons thought about quitting and going into real estate since there was little money in sportswriting but didn't. He is considered to be one of the first stars of the Internet generation of sports writers because he embraced the Internet when not many writers were. In 2001, his website averaged 10,000 readers and 45,000 hits per day.

Career at ESPN

Simmons gained notoriety as "The Boston Sports Guy" which earned him a job offer from ESPN in 2001 to write three guest columns. His first column was "Is Clemens the Antichrist?" which became one of the most e-mailed articles on the site that year. Simmons quickly became the most popular columnist on the site and was given his own section of ESPN.com's Page 2, which helped both himself and Page 2 gain widespread popularity. In the first sixteen months which Simmons wrote for Page 2 the viewership doubled. In late 2004 ESPN launched an online cartoon based on his columns which Simmons later called a "debacle" which he had decided to quit. Simmons writes several columns per week for his page titled "Sports Guy's World."

As a lead columnist, Simmons is one of the country's most widely read sports writers and is considered a pioneer of sportswriting on the Internet. His readership has steadily grown since he started at ESPN.com in 2001. In 2005, according to ESPN, Simmons' column averaged 500,000 unique visitors a month. According to comScore, Simmons's column had averaged 1.4 million pageviews and 460,000 unique visitors a month over the previous six months in November 2009.

In 2007, Simmons conceived the idea for the critically praised 30 for 30, a series of documentaries chronicling 30 stories from the "ESPN era." Each of the documentaries detail the issues, trends, people, teams, or events that transformed the sports landscape since the sports network was founded in 1979. He wanted feature filmmakers to recount the sports stories, people, and events from the past three decades in which they took a personal interest or involvement, however great or small, and felt that said stories had not been fully explored. Simmons and his team took special interest to "stories that resonated at the time but were eventually forgotten for whatever reason." The series premiered on October 6, 2009 with "King's Ransom" directed by Peter Berg. Simmons serves as executive producer on the project.

On May 8, 2007, Simmons began a podcast for ESPN.com called Eye of the Sportsguy. On June 14, 2007 the podcast was changed to The B.S. Report with a new theme song written by Ronald Jenkees. Simmons creates three or four hour long podcasts a week, generally carrying one theme throughout, talking to everyone from sports and media notables to his friends. The B.S. Report is regularly the most downloaded podcast on ESPN.com averaging 2 million downloads a month. In 2009, The B.S. Report was downloaded more than 25.4 million times. Simmons guests includes athletes and writers such as Malcolm Gladwell and Chuck Klosterman and his friends such as Jacko (Yankees fan John O'Connell), Cousin Sal (Sal Iacono) and Joe House.

Simmons began writing a weekly, 800 word column for ESPN The Magazine in 2002 but convinced ESPN after three years to give him 1,200 words. In the July 27, 2009 issue of ESPN The Magazine, Simmons officially announced his retirement from his magazine column. He continues to write for the ESPN.com Page 2 website.

In October 2007, it was announced the Simmons joined the television series 60 as a special contributor. His current contract with ESPN, which he signed in 2007, expires in 2010. In May 2010, it was reported that Simmons and ESPN came to an agreement on a new contract, although no official announcement has been made on the terms.

Outside of ESPN, most notably, Simmons has served as a writer for Jimmy Kimmel Live! and written two best-selling books. Simmons has also appeared on VH1's I Love the '90s, PTI's Free Agency Summit, and is an occasional guest on several sports talk radio shows. For the week of September 21, 2010, Simmons served as guest host on Pardon the Interruption.

Jimmy Kimmel Live!

In the summer of 2002, Jimmy Kimmel had been trying to get Simmons to write for his new late-night talk show, Jimmy Kimmel Live! which was to premiere after the Super Bowl. Simmons refused for most of the summer because he didn't want to cut back on his columns and move to the West Coast away from his family and Boston teams. Kimmel kept on "badgering" him and by mid-September Kimmel had him "on the ropes." It was crucial for Simmons that he could write for the show and on ESPN.com and in ESPN The Magazine, which was possible because of the Disney connection with ESPN and ABC. He has also stated that he joined the show because he was burned out from his column, felt he needed a change, and always wanted to write for a talk show.

Simmons left Boston and moved to California on November 16, 2002 and began working in April 2003 as a comedy writer for the show. Simmons called it "the best move I ever made" and said it was one of the best experiences of his life. He left the show in April or May of 2004 after a year and a half of writing for the show. Simmons left because he felt the show was a logical move to a potentially ridiculously, lucrative career path. He also wanted to focus full time on his column since his writing was starting to slip and he didn't have enough time to work on columns or even think about them. Simmons remained in California.

Books

On October 1, 2005, Simmons released his first New York Times best-selling book, Now I Can Die in Peace. The book is a collection of his columns, with minor changes and lengthy footnotes, leading up to the 2004 World Series victory by the Boston Red Sox. The book spent five weeks on The New York Times extended best-seller list.

In July 2008, Simmons announced that he would be taking 10 weeks off from writing columns for ESPN.com's Page 2 to concentrate on finishing his second book, The NBA According to the Sports Guy, which was released on October 27, 2009. The book tries to find out who really are the best players and teams of all time and the answers to some of the greatest "What ifs?" in NBA history. It debuted at the top of The New York Times Best Seller List for non-fiction books.

When Simmons' first started his website, he wrote what he thought friends would enjoy reading because he never understood how people could be sportswriters while claiming they did not to care which team won, in the name of journalistic objectivity. Since Simmons was writing on the web he figured that "in order to get people to read it, it had to be different from what people got in newspapers and magazines." He believes his job is not to get into the heads of the players, but into the heads of his readers. One way he gets his readers to come back is to update frequently and to be provocative, so he can get a discussion going among and with his readers. Simmons has stated that he "...will never write a traditional sports column."

With his column, Simmons aims to speak for, reconnect sportswriting with, and reproduce the experience for the average fan. Simmons' writing in his columns is characterized by mixing sports knowledge, erudite analysis, clever prose, comedy, references to pop culture including movies and television shows, his non-sports-related personal life, his many fantasy sports teams, video games, and even throwing in a few references to adult video. His columns often mention trips to Las Vegas or other gambling venues with his friends, whether it's at the blackjack table or sports gambling.

One of his most popular recurring columns is the "Mailbag" where he answers readers' e-mails. He almost always ends these columns with a strange e-mail, followed by the statement "Yup, these are my readers." He also occasionally engages in lengthy chat sessions with readers on ESPN.com. His wife occasionally writes mini-articles within Simmons' own Page 2 articles as "The Sports Gal," on subjects such as The Hills and her lack of understanding of a golf handicap.

Feud with ESPN

Simmons has at times had a tense and public battle with ESPN about creative freedom and censorship. In May 2008, Simmons was embroiled in a feud with management at ESPN.com. When asked by the editors of Deadspin why he had not written a new column in over 2 weeks, he said that he was writing less because he loved writing his column and believed that he and ESPN had come to an agreement "on creative lines, media criticism rules, the promotion of the column and everything else on ESPN.com" but within a few months all of those things changed.

A month before the feud erupted, Simmons was scheduled to interview then Sen. Barack Obama for a podcast. Obama was still running against then Sen. Hillary Clinton for the Democratic Nomination at the time. ESPN nixed the interview, saying that they would only allow its reporters and columnists to interview a presidential candidate once the nomination had been finalized. Deadspin believed this was an example of ESPN pulling rank, and speculated that ESPN was thinking that they should wait for Stu Scott to talk Carolina hoops with Obama after the convention instead of on a podcast. According to a campaign source, a television interview Stu Scott was canceled by higher-ups as well. Stu Scott eventually did interview Obama right before the convention began.

On October 31, 2008, ESPN refused to post Simmons' NFL Week Nine Picks, instead just putting up his predicted lines. In response to many reader emails, Simmons posted to his blog explaining what happened (which has since been removed from his personal blog).

In November 2008, according to Deadspin, Simmons had quit the B.S. Report due to the content being edited out of them. The controversy revolved around the entry of pornography actor Christian into a ESPN fantasy basketball league. Simmons was upset that his explanation of ESPN's refusal to allow him into the league was edited out of a B.S. Report podcast. On November 25, 2008, Simmons returned to recording his B.S. Report podcast with a disclaimer, which says "The BS report is a free flowing conversation that occasionally touches on mature subjects."

In late 2009, 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 with an exception for tweets about his book tour.

Isiah Thomas

A frequent column target for Simmons in the past has been former New York Knicks coach and general manager Isiah Thomas. This led to Thomas threatening Simmons on Stephen A. Smith's radio show in early 2006, saying that there would be "trouble" if they ever met in the street. In 2007 Simmons stated that he and Thomas had a half-hour long chat, facilitated by sports announcer Gus Johnson, about Simmons' criticisms of Thomas, and that Thomas remained civil and cordial throughout.

Red Sox Nation presidency

Simmons and Red Sox announcer Jerry Remy feuded over the presidency of Red Sox Nation. The Red Sox asked Simmons to run for the ceremonial position and he accepted. In a candidate's memo, Simmons remarked that he was a better choice than Remy because he is not a smoker. Remy criticized Simmons for about five minutes during the July 16, 2007 NESN broadcast of the Red Sox - Royals game. Simmons later removed himself from consideration and Remy was named president.

Simmons responds to issues in the sports world in a unique way, usually putting a different spin on events, ideas and theories contributing to memes. He uses such terms so frequently that ESPN.com has a glossary of Simmons conventions, with links to articles in which they were used.

Ewing Theory

One of Simmons's most used internet memes has been the famous Ewing Theory, which was conceived by Dave Cirilli and named after Patrick Ewing of the New York Knicks. In 1998-99, the Knicks made the NBA Finals after Ewing sustained an Achilles' tendon injury. Thus, the Ewing Theory claims that when a longtime superstar who has never won a championship leaves the team via injury, trade, or free agency, and the media writes the team off, the team will play better.

Given the time since the name Ewing Theory was coined and the Giants' Super Bowl XLII victory, a number of readers suggested the name be updated to the "Tiki Theory" named after former player Tiki Barber and Simmons agreed.

Manning face

The Manning face is a known facial expression displaying a mix of frustration and disgust. It is most often displayed by NFL quarterbacks Peyton Manning and his younger brother, Eli. It was coined in 2004 and was later defined by Malcolm Gladwell as "the look of someone who has just faced up to a sobering fact: I am in complete control of this offense. I prepare for games like no other quarterback in the NFL. I am in the best shape of my life. I have done everything I can to succeed - and I'm losing. Ohmigod. I'm not that good."

The Manning Face references receded from Simmons' columns during the 2006-09 stretch when each brother won a Super Bowl and Peyton won two MVP awards, but Simmons noted it returned during the Colts' Super Bowl XLIV loss to the New Orleans Saints, after Tracy Porter intercepted Peyton's pass and returned it 74 yards for the title-clinching TD. He later said it wasn't clear whether the Face was returning for good or made a cameo appearance.

Levels of Losing

Another recurring Simmons topic is the 16 Levels of Losing (originally 13 Levels of Losing), where he defines, describes and ranks the most painful ways for a sports team to lose, such as the "Stomach Punch", or the "Guillotine". Simmons defined Game 6 of the 1986 World Series as the highest level of losing.

The Tyson Zone

Simmons also created the "Tyson Zone," named in honor of boxer Mike Tyson. The Tyson Zone is the status an athlete or celebrity reaches when his or her behavior becomes so outrageous that one would believe any story or anecdote about the person, no matter how shocking or bizarre. The term may also be used in adjective form as the word "Tysonic."

Simmons is married to Kari Simmons (née Crichton), mentioned only as "The Sports Gal" in his columns. They have two children together, daughter Zoe Simmons, born in 2005 and son, Benjamin Oakley Simmons (called "The CEO" by Simmons and his wife), born in November 2007. His father, William Simmons, is also referred to as "The Sports Dad."

Rooting interests

A native New Englander, Simmons is a devoted fan of Boston's teams including Boston Red Sox, New England Patriots, and Boston Celtics. He was a longtime fan of the Boston Bruins and the NHL, but claims that their poor management led to his completely losing interest in them until the 2008 playoffs. He is also a Los Angeles Clippers season ticket holder.

He also passionately roots against certain teams, specifically the Indianapolis Colts, Los Angeles Lakers, New York Yankees, Duke University Men's Basketball, New York Jets, and the Montreal Canadiens.