I don't think it seems like they hired the most connected guy. I don't think they hired Dan or Jason simply because they were friends with them in the past. I think they hired them because they have years of experience and are a fantastic fit for the job that would need to be done at Giant Bomb.
Look at it this way.
Imagine that after Jeff got fired, that Ryan kept working at Game Spot. Then, 2014 comes, and Jeff hires Ryan. We already know that Ryan worked fantastically well at GB and Ryans main criteria was "years of experience in the industry, a friend of the people who work at Giant Bomb currently, tons of video experience, and a prominent, distinct, entertaining on screen personality."
There are absolutely solid grounds for someone to see Dan Ryckert and Jason and say that those are a perfect fit for the job at hand.