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How ESPN personalities' careers fared after they left the 'worldwide leader in sports'

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Will Bill Simmons be the exception to the rule that nobody’s allowed to become bigger than the four letters at ESPN?

The news that Simmons is joining HBO with a multi-year, multi-platform deal raises the question, again, whether the grass is greener beyond the Worldwide Leader’s insular campus in Bristol, Conn.

MORE: Greatest moments in ESPY history | Bill Simmons joins HBO

Robin Roberts, Dan Patrick, Rich Eisen and, most recently, Erin Andrews have all gone on to fame and fortune elsewhere. 

Patrick’s old SportsCenter running mate Keith Olbermann is on his way out the door again at ESPN. Ditto for radio host Colin Cowherd, who’s rumored to be heading to Fox Sports. Jason Whitlock’s encore with the WWL has turned into an embarrassing disaster. 

For my money, Simmons could not have landed in a better place than the creatively focused HBO, which boasts talent ranging from Bryant Gumbel to Jon Oliver. The outspoken columnist will be free to tell it like it is — without ESPN brass coming down on him.

As Simmons said in a statement regarding his new deal, "It’s no secret that HBO is the single best place for creative people in the entire media landscape. From the moment I started talking to (HBO president) Michael (Lombardo) and Richard (Plepler, HBO chairman and CEO), it was hard to imagine being anywhere else." 

James Miller, co-author of the best-selling Those Guys Have All the Fun: Inside the World of ESPN, tweeted, “there will be another announcement in the future as to where he will call home for ‘digital.’” 

Translation: Simmons could launch a web site similar to Grantland that he launched for ESPN.

But sometimes the best trades are the ones you don’t make. For every Eisen success story, there are cautionary tales like Craig Kilborn (remember him?) who left ESPN for the bright lights of entertainment only to end up in the career Witness Protection Program.

Simmons is a better columnist/podcaster than broadcaster. There are no guarantees of success for him or anybody else on TV. 

Fox Sports’ Joe Buck tanked on HBO when foul-mouthed comedian Artie Lange hijacked his Joe Buck Live premiere in 2009. Buck’s show was canceled after only three episodes. 

Likewise, columnist Rick Reilly foolishly ended his award-winning 23-year run with Sports Illustrated in 2007 to try to become a Jack Whitaker-type TV essayist with ESPN in 2007. He flopped too.

Let’s take a look at some of the big TV personalities who’ve left ESPN — and grade their post-Bristol careers.

 

Bill Simmons

Bill Simmons

What he did at ESPN: The one-time bartender vaulted from obscurity when he joined ESPN in 2001. He quickly became the most popular columnist on ESPN.com, encouraging a generation of young talent. He served as editor-in-chief of the critically acclaimed Grantland.com, helped ESPN challenge HBO Sports’ supremacy in sports documentaries with his well-regarded 30 for 30 series, and his B.S. Report podcast was one of the best in sports media. But Simmons was suspended by his bosses for his harsh criticism of NFL Commissioner Roger Goodell (ESPN is in business with the NFL, holding the TV rights to Monday Night Football). Plus, Simmons lost his rabbi when longtime ESPN executive John Walsh retired. ESPN boss John Skipper then dropped the bomb in May by publicly declining to renew Simmons contract. That made one of the country’s highest-paid sports columnists a free agent.

What he’s doing now: Simmons joined HBO, where he’ll produce his own weekly talk show focusing on sports and pop culture in 2016. For a talent who chafed under his bosses at ESPN, Simmons could not have landed in a better spot. HBO lets outspoken personalities such as Bryant Gumbel and Jon Oliver tackle whatever topics they want. Simmons tweeted his podcast will return Oct. 1 under a new name with new corporate sponsors. Now we have to wait and see whether Simmons will launch a Grantland-like digital offering to stick it to his old bosses in Bristol. Simmons is clearly not done tweaking Goodell either. He recently tweeted that “Goodell screwing up” is among the “most reliable” sports wagers.

Grade: A

Colin Cowherd

Colin Cowherd

What he did at ESPN: Ex-sports anchor took off nationally after joining ESPN in 2003 and became one of ESPN’s biggest radio stars. While co-host Michelle Beadle got most of the credit, Cowherd was unsung star of SportsNation. But the outspoken Cowherd has sparked plenty of controversy. He implied Washington Redskins star Sean Taylor’s checkered past somehow caught up with him when he was murdered in his own home. Turned out that Taylor was the victim of a random robbery. Cowherd stepped in it again recently by insulting people from the Dominican Republic. ESPN pulled him off the air with one week left on his contract. Still, Cowherd’s one of the few talents to say no to Bristol. When his contract was up, ESPN tried hard to re-sign him (unlike Simmons). But Cowherd declined, choosing to team up with ex-ESPN star exec turned Fox Sports president Jamie Horowitz.  

What he’s doing now: Beginning September 8, Cowherd will host a daily three-hour show on Fox Sports 1 and the Fox Sports Radio Network. He’ll also join Fox NFL Kickoff, which will air at 11 am before the flagship Fox NFL Sunday.

Grade: B

Robin Roberts

Robin Roberts

What she did at ESPN: Served as SportsCenter anchor from 1990 to 2005 before moving to the news side at sister Disney network ABC.

What she’s doing now: Roberts co-anchors the country’s top-rated morning show, Good Morning America. After moving to morning news full-time, she helped pull off the nearly impossible task of overtaking top-ranked NBC’s Today show in ratings. She was the first journalist to interview President Barack Obama after his inauguration and is a beloved breast cancer survivor. 

Grade: A

Dan Patrick

Dan Patrick

What he did at ESPN: Patrick and Olbermann helped make ESPN cool with their SportsCenter “Big Show” in the 90s.

What he’s doing now: After serving 18 years at what he calls the “Mothership," he launched his own nationally syndicated radio show in 2007. The Dan Patrick Show is simulcast on NBC Sports and DirecTV. He's the co-host of NBC’s Football Night in America and serves as senior writer for Sports Illustrated.

Grade: A

Rich Eisen

Rich Eisen

What he did at ESPN: SportsCenter anchor from 1996 to 2003.

What he’s doing now: Eisen was the first on-air talent hired by the NFL Network when it launched in 2003. He’s now the voice and face of NFL Network and, in 2014, began a three-hour live program (carried by DirecTV and Fox Sports Radio) called "The Rich Eisen Show." He also hosts a laundry list of shows including NFL Total Access, NFL GameDay Final and Thursday Night Football. He's known for his witty appearances on VH1 and is an author as well.

Grade: A

Erin Andrews

Erin Andrews

What she did at ESPN: Became a national sensation during her eight-year run as a sideline reporter from 2004-2012 before accepting a lucrative offer from Fox Sports.

What she’s doing now: She struggled with hosting Fox’s first college football pregame show before replacing Pam Oliver on Fox’s top NFL announcing team with Buck and Troy Aikman. She's now serving as sideline reporter for virtually all of Fox’s big sports events, including NFL and MLB’s World Series and All-Star Game. She parlayed her appearance on ABC’s Dancing with Stars as a contestant into a co-hosting role. She's a popular endorser on Madison Avenue. 

Grade: B

Michelle Beadle

Michelle Beadle

What she did at ESPN: Beadle turned SportsNation from a new show into big hit during her first stint from 2009 to 2012. She made the mistake of jumping to NBC Sports, which didn’t know what to do with her. Her show, The Crossover with Michelle Beadle, lasted less than a year.

What she’s doing now: She wisely returned to ESPN’s SportsNation in 2014, where she’s back to her smart, funny self. She's a must-follow on Twitter. 

Grade: B

Keith Olbermann

Keith Olbermann

What he did at ESPN: One of the best SportsCenter anchors of all time during his first ESPN stint from 1992 to 1998.

What he’s doing now: He's a hyper-talented anchor who doesn’t just burn his bridges, he “napalms” them, in the words of one ESPN executive. He achieved his greatest post-ESPN fame as a liberal pundit for MSNBC. He only lasted two years in his return to ESPN. But don't blame him for the breakup. He was a good soldier. Blame Bristol for not giving him better time slots.

Grade: C

Jason Whitlock

Jason Whitlock

What he did at ESPN: Page 2 columnist from 2002 to 2006. Returned in 2013 to oversee the launch of a new race in sports website called The Undefeated.

What’s he doing now: Jason Whitlock’s second stint with ESPN looks like it will end the way the first one did — badly.

The columnist was recently demoted as boss of his own embryonic ESPN site, The Undefeated, and his byline stripped from the title.

Now, SportsBusiness Daily reports Whitlock’s negotiating to get out of his ESPN contract early to return to his old stomping grounds at Fox Sports. Ex-ESPN honcho Jamie Horowitz recently joined Fox Sports and brought in Whitlock’s ESPN colleague Colin Cowherd.

A move to Fox could be a big career plus for Whitlock. During his first go-around with Fox, he hilariously threw shade at ESPN personalities such as Mike Lupica and Scoop Jackson. He hasn’t been as brave or crazy since.

Horowitz has a great reputation for nurturing talent and creating hits. So if you’re keeping score, Whitlock went from ESPN to Fox to ESPN and now probably back to Fox. Got it?

Grade: C

Craig Kilborn

Craig Kilborn

What he did at ESPN: Took off as SportsCenter anchor from 1993 to 1996.

What he’s doing now: Trivia question. Who hosted Comedy Central’s The Daily Show before Jon Stewart? Yep, it was Kilborn who hosted it and a late-night talk show before disappearing from the radar. Kilborn became a human punchline for The Onion, which satirically portrayed the “gin-soaked” anchor returning to his SportsCenter studio and forcibly trying to remove “wannabe” Scott Van Pelt from his chair.

Grade: F

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