The early days of televised professional sports transformed athletes and even coaches into celebrities. Vince Lombardi, Joe Namath, and other on-field stars became household names, much like the film and television stars of Hollywood. At the time, sports writers were simply messengers for those on the field to address fans and critics. Over the decades, this dynamic has dramatically changed. Fans once trusted media outlets—Sports Illustrated, ESPN, USA Today, The Sporting News—to bring them scores, news, and analysis of their favorite teams. These organizations were known, respected, and hired the best journalists in the business. Today’s fans trust people more than company mastheads, following their favorite media celebrities across the Internet. Sportswriters make a name for themselves with elegant prose, edgy opinions, and lightening quick breaking news reports. Ego, skill, and drive elevate some writes from the fringe to the green. The best-of-the-best parlay a devoted reader following into big dollars and all-powerful editorial control over their own work.

In the early 2000s, Bill Simmons grew into a star at ESPN, combining a unique writing style with a willingness to challenge the status quo. Page views and shares of his articles were tough to match. His popularity among fans ballooned while his influence within the walls of the media powerhouse strengthened. Simmons transformed upstart ESPN projects like the sports documentary series 30 for 30 and The B.S. Report podcast into big-time successes. He butted heads with ESPN brass throughout his time with the company, yet his popularity eventually stemmed from the creation of Grantland, an ESPN-backed, Simmons-run online magazine. The sports and pop culture website found a loyal following while the editor kept aggravating his bosses. Sadly, Grantland was shuttered this past fall, just months after ESPN chose not to renew Simmons’ contract. Because fans rely on Simmons for his controversial voice among the whitewashed thoughts of his peers, ‘The Sports Guy’ landed firmly on his feet with HBO. The newly formed Bill Simmons Media Group will develop Bill’s new HBO talk show, create a content website, and flush out an already growing podcast network. In past decades, sports writers cutting against the grain were blackballed from the industry, often landing on sports desks in Nebraska or Alaska. Now that writers like Bill Simmons have developed their own brands, it’s easy to follow them from destination to destination.

It’s hard to fathom how Yahoo! Sports has kept Adrian Wojnarowski on staff since 2007. Woj is widely considered the best NBA scooper in an age where insider information means everything. His link to Yahoo! Sports has kept the online website credible despite its outdated page designs and lack of meaty content. Yahoo leadership recognizes Woj’s talent and lured him to sign a new contract this past summer with the promises of his own NBA-focused website and podcast, both entitled The Vertical. The allure of a somewhat standalone website backed by Yahoo’s infrastructure and viewership kept Wojnarowski from jumping ship. Woj could have easily left for another major content website or done his own thing, like Chris Sheridan of Sheridan Hoops. He controls his own career because he’s recognized as much more than just another Yahoo reporter. Consider this: the @YahooSports Twitter username has over 375K followers—not too shabby—but Woj’s @WojVerticalNBA username has an overwhelming 1M-plus followers. Adrian Wojnarowski’s great work and amazing following earned him his money and plenty of creative control.

Few NFL sports writers are more celebrated than Peter King. The Senior Writer at Sports Illustrated has spent over 3o years breaking news and dishing out opinions on the most popular professional sport in America. He’s also been part of NBC’s Football Night in America program for nearly a decade. King isn’t a flash-in-the-pan sports personality welding a blog and a podcast. He’s a time-tested, award-winning writer and reporter —two Associated Press Sports Editor awards, multiple National Sportswriter of the Year awards, and recipient of the McCann Award, among others—who’s done the work long enough and well enough to write his own ticket. The Sports Illustrated executive team created The MMQB website handing King a team of talented writers to develop football content for diehard football fans. Why doesn’t SI keep his work exclusively on their website? Because Peter King has the following to strike out on his own if he so chooses. So Time Warner, SI’s parent company, created a giant sandbox for King to play in and handed him the tools to make whatever castles and moats he pleased. Peter King is so synonymous with the National Football League that SI will do whatever it takes to keep him feeling happy and challenged.  

The craze of celebrity sports writers has heated up over the last decade. Twitter has made it simple to follow the most talented scribes. The Internet allows for content creation by even the most technologically defeated writers, while television producers are always looking for “experts” in suits to break the news and opine about the day’s happenings. Every sports writing career begins with words on a page. Where it goes depends upon your talent, efforts, and willingness to take a chance. Perhaps it’s time to take a chance?