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On December 4, Red Sox slugger David Ortiz will announced the details of his retirement through Derek Jeter’s media startup, The Players’ Tribune.

And he’s doing it an unprecedented way.

He’s holding a live Internet press conference in his home country, the Dominican Republic, from the golf course during his 8th Annual David Ortiz Celebrity Golf Classic.

An internet press conference isn’t so unusual, but in this case, The Players’ Tribune is also going to allow 1,000 fans to virtually attend the video conference, and give a few of them the chance to talk with the baseball star and ask him questions over the internet.

And the whole situation has Blue Jeans Network’s CEO Krish Ramakrishnan alternatively thrilled and biting his nails, he told us. 

That’s because the event will take place through Blue Jeans Network, a hot Valley startup with a video conference platform that allows people on different video conference apps to chat together, i.e. Skype, Google Hangouts, Cisco’s big room-sized conferences, etc.

The nerve wracking part: when Kobe Bryant announced his retirement on The Players’ Tribune, the website was so overwhelmed with visitors, it crashed.

Ramakrishnan has got his team working hard to make sure the live, internet press conference doesn’t crash.

Packed as it will be with sports reporters from all over the country, if there are problems with the livestream or question/answer process, he knows Blue Jeans will be fried in the press. And he’s got no control over the quality of the internet connection in the Dominican Republic.

Still, if the live event works well, this will be yet another way that Jeter’s startup is trying to take on and change the media industry.  And it will be a big feather in Ramakrishnan’s cap. 

Jeter’s startup has gotten a lot of attention because the articles are written by current and former pro athletes (including a touching series called “Letter to my younger self“).

But clearly Jeter envisions more ways that athletes can connect directly with fans via video.

Jeter was an investor in Blue Jeans in the $76.5 million round it raised in September. He met Ramakrishnan through the VC that backed The Players’ Tribune, NEA’s Jon Sakoda. NEA is also one of Blue Jeans major investors.

Jeter also integrated Blue Jeans technology into The Players’ Tribune website.

And in a couple of days all of it will be put to the test on a worldwide stage.

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