There are no longer people in sports media.  Rather, sports media has become populated with multi-platform personalities, with importance stressed on becoming a “sports media brand” instead of just being on-air talent.  New media partnerships have been happening for years now, and a handful of the most notable ones can be judged as they have more or less played out.

There are a share of success stories, some people have returned to their old jobs, and the unluckiest souls have been climbing out of ruts ever since.  Bill Simmons, Keith Olbermann, and Colin Cowherd are all leaving ESPN for other entities, all of them hoping to increase and improve their personal sports media brands.  This big name trio might want to consider how their contemporaries have fared before launching new ventures.  Nine notable examples are profiled below.

Mike Lupica to The National
In 2015, the idea of any newspaper, let alone one devoted completely to sports, is completely crazy.  But in 1990, long before the advent of web journalism (and blogs like AA), a national daily sports publication sounded like a good idea.  Emilio Azcárraga, who also owned the Spanish-language network Univisión, founded The National in 1990 and hired Frank Deford as editor-in-chief.  Mike Lupica was already an established writer by the time he was brought on board, with five books published and a column in the New York Daily News, and he was one of many well-known commodities under Deford.

Nowadays, Lupica chooses to omit his time with The National from his resume because he couldn’t even make it the full year and a half before the paper itself shuttered.  Lupica quit before The National went under, even though Grantland’s oral history of the publication makes it sound like he was mailing it in from day one.  Considering the rapidity with which the newspaper went under, I don’t think Lupica giving his best effort would have made a difference on that front, but it sounds like he made a handful of enemies from his time there.  Since this valley in his career, Lupica has published a plethora of books, is still a Daily News columnist, and even does some TV and radio work at ESPN.
Verdict: Failed new media partnership, but no major impact on his career.

Adam Carolla to Carolla Digital
The former Loveline co-host was a West Coast syndication replacement for Howard Stern after Stern left terrestrial radio.  The original Adam Carolla Show was based out of KLSX in Los Angeles from 2006-2009.  In 2009, KLSX was relaunched as KAMP, a Top 40 station that ditched all of its predecessor’s hot talk.  Literally days after his radio show ended, Carolla released his first standalone podcast, which quickly launched to the top of the iTunes charts.

Over the years, that single podcast has evolved into Carolla Digital, an umbrella company for all of the podcasts he hosts and that his company produces.  Some of the podcasts did not get a lot of traction, but The Adam Carolla Show has earned podcasting awards en route to the Guinness World Record for most downloaded podcast of all time.
Verdict: Very Successful

Howard Stern to SiriusXM
Howard Stern rose to fame just like modern reality television stars, by broadcasting an extreme and enhanced version of himself to the masses.  After two decades in syndication, the self-proclaimed “King of All Media” felt beaten down by FCC rules and regulations.  Stern contends that he would have quit radio all together had satellite not emerged as an option.  The pay also helped, as he originally signed a five year deal worth $500 million before re-signing for another five years.  His current deal ends in late 2015, and he might not re-sign.

Five years ago, Stern re-signed with SiriusXM at the last minute, so that is another possibility considering the host has leverage.  Howard Stern is a big reason American public has adopted the satellite radio medium, but the subscriber base for SiriusXM could drop quickly if they can’t re-sign Stern.
Verdict: Wildly Successful

Chris Russo to SiriusXM
The more volatile half of WFAN’s top duo decided to jump ship after 19 years paired with Mike Francesa.  The pair had their share of fights after nearly two decades hosting Mike and the Mad Dog, fights that eventually led to a radio breakup and saw SiriusXM hire Russo to headline his own channel, “Mad Dog Radio.”  His original contract was worth $15 million over five years and it is likely SXM lost money over this period.  Russo re-signed with the satellite radio company, but there were a lot of contingencies added and, most importantly, a lower salary.

Aside from a rebranding of his station to “Mad Dog Sports Radio,” he added High Heat, an MLB Network show simulcast on MLB Network Radio, while contracting his daily show from five hours to just three.  Russo was set to be a sports version of Howard Stern over at SXM, but he did not have the pull or popularity to make MDR a success.  That said, the recent addition of Stephen A. Smith to the station could be a saving grace.  If not, there have been murmurings of a reunion between Russo and Francesa, whether it be on SiriusXM or terrestrial radio, which could be a sign his time on satellite radio is in its final chapter.
Verdict: Underwhelming

Graham Bensinger to In Depth with Graham Bensinger
The Emmy-winning Bensinger is likely the least recognizable name on this list.  Even if you’re a huge ESPN fan, you might only know Bensinger as the guy who got Terrell Owens suspended in 2005.  His radio show was national before he could drink and, after leaving ESPN, Bensinger went out on an island, starting an interview show called In Depth with Graham Bensinger.  There was no safety net tied to ESPN, Fox, or another broadcasting entity.  Bensinger wanted to have editorial control over his interviews and decided a syndication model would be best for the show.

His reach has grown to more than ¾ of the United States and has even evolved into a secondary partnership with Yahoo! Sports for show highlights.  No other sports show is structured or broadcast in the same manner as Bensinger, and he keeps doing it, so some things must be going well.
Verdict: Growing Success

Glenn Beck to TheBlaze
Beck was very successful on political talk radio and cable television in the 2000s between national radio syndication and an evening slot on Fox News.  In 2011, he took a risk and decided to go out on his own.  Beck started an online network called TheBlaze (originally GBTV), which originally operated solely on a subscription model.  TheBlaze began simulcasting Beck’s radio show while also turning into a legitimate political network.  Had TheBlaze failed, Beck’s stock would have taken a hit, but his strong ratings on cable would have gotten him another job there while Premiere would have continued syndicating his radio show.

Luckily for Beck, TheBlaze has been an extreme success, leading to carriage from select cable providers, an internet/satellite radio network, an app with between 100,000 and 500,000 downloads on Google Play, and a website ranked in the top-1000 by Alexa.  In case you couldn’t tell, Glenn Beck is swimming in money.
Verdict: Extremely Rich and Successful

Keith Olbermann to Current TV
There’s something about Keith Olbermann that sees him returning to his former stomping grounds on multiple occasions.  His second tenure at MSNBC began in 2003 with KO hosting Countdown with Keith Olbermann.  After signing a four year extension in 2007, the relationship between MSNBC and the host began to sour.  After being let go at MSNBC, Olbermann bounced back quickly and found a home at Al Gore’s network.

It was short lived, as he was fired after little more than a year on the network.  Since Olbermann’s time at Current ended, the network has become Al Jazeera America and another ESPN era has come and gone for the host.  Current rumors have him starting a third stint at MSNBC, of all places.
Verdict: Brief, Problematic, and Unstable

Katie Couric to Yahoo!
Remember when Couric was the big name on Today alongside Matt Lauer?  After leaving Today to make history on CBS as the first solo female national news anchor, she decided to step down from the CBS Evening News in 2011 to pursue other opportunities.  The first of these was a daytime talk show that flopped after two seasons.  With all of those ventures in the rear view mirror, Couric now works for Yahoo!, which you might not even be aware of.

If Yahoo! is your home page, you’ll see her interviews.  Otherwise, maybe not.  Many are exclusives with big names, including recent videos with Bernie Sanders and Charli XCX, but The Street has argued that ad revenue has not matched Couric’s multi-million dollar salary.  That said, she re-upped with the internet giant in June, which means they either like losing money, or Couric has had some value for Yahoo! since she signed on almost two years ago.
Verdict: Questionable, but Yahoo! Reinvested

How does this affect Bill Simmons and HBO?
Just this week, it was revealed that the former Grantland guru had signed a contract with the premium tier cable network to host a new weekly talk show.  It also sounds like there will be some sort of an internet video portion to Simmons’ HBO tenure, similar to the video podcasts he did at Grantland.  At its best, Simmons could turn his HBO venture into a sports version of Carolla Digital combined with a television arm similar to TheBlaze.  At its worst, this is the beginning of Simmons bouncing around like Katie Couric or Keith Olbermann, living off of huge successes that are not matched by new results.

In my opinion, he’s closer to KO in this regard because they both have encyclopedic sports knowledge, harsh opinions (especially on Roger Goodell), and polarizing personalities.  Heck, both have pissed off ESPN management to the point of dismissal, which isn’t exactly a typical occurrence in Bristol.  Neither endpoint is a legitimate outcome for the new Simmons/HBO partnership, but unless his personality gets in the way, he should be fine.  I also believe his talk show will be more successful than Joe Buck Live and Costas Now, though that’s not necessarily a high bar to compete with.

How does this affect Keith Olbermann post-ESPN?
As I said before, KO has been linked to MSNBC, where his return would signal a third stint at the network.  Clearly, this would be the exact opposite of a new media partnership, which makes sense based on how his Current TV era ended.  Once the sheen of the “splashy hire” wears off, the relationship between Olbermann and upper management wears down to the point of dismissal or non-renewal.

If MSNBC isn’t as close as the rumor mill says, then KO might want to consider becoming his own boss through video podcasting.  He could upload commentary online without fear of bosses limiting him.  However, it might be a lot of work that the 56-year-old Olbermann wouldn’t want to take on.  His other new media partnerships, such as Current TV and, to a lesser extent, the launch of ESPN2, have been far from successes, which could also lead to trepidation regarding a third attempt.  Regardless, a third attempt at MSNBC can’t end any worse than his second one.

How could this affect Colin Cowherd at Fox Sports?
Though Cowherd hasn’t officially revealed his new destination, it is essentially a done deal that he is leaving ESPN for Fox Sports.  He has hinted at a presence on SiriusXM and a simulcast, both of which could lead to him replacing or preceding Mike Francesa on Fox Sports 1 or 2.  The 9-12 slot on Fox Sports Radio is currently inhabited by Dan Patrick, while the 12-3 slot is currently filled by Rich Eisen.

With a full slate of programming, Cowherd might have to forego syndication for the time being, but he will have television carriage in ten million more homes, a number that will likely increase as FS1 continues to grow.  Combined with a standalone television presence produced by his buddy Jamie Horowitz, the potential for Cowherd is to become the big name at FS1/2.  He could eclipse Jay and Dan and help at least a few more people learn where Fox Sports 1 is on the cable guide.

How could this affect future new media partnerships?
As more and more sports media personalities work to evolve into sports media brands, they will likely outgrow their setups and try to branch out to multiple platforms.  These people will populate a new generation of personalities, with plenty of past examples to learn from.

Some of these have been successful, mutually beneficial moneymakers for both the personality and the network, but others have been far from that.  Truly, it takes just the right mix of personality, structure, and funding to make a new media partnership work. The only guarantee is that we’re going to see more of these partnerships in the future as the media landscape continues to change.