The Ortiz announcement made me go on that site and take a look at it. I was quite puzzled by it. How is the Player's Tribune supposed to make money exactly? There were no obvious signs of advertising; the content doesn't particularly unique, to attract a big enough audience that would help generate subscriptions or licensing revenue..Are the players paying something to write those pieces? On the flip side, it looks and feels expensive, so you know somebody's getting paid..
This looks like a vanity project that will die quickly when Jeter/Ortiz/whoever decide they don't want to sink money in it any more.