The Toronto Maple Leafs have developed some fantastic players over the years, but as we've seen before, when they leave for greener pastures, sometimes it's not quite the same.
In that time, he played a key role for a very talented group, tallying 11 goals and 82 points while providing a physical presence on the back end, but now, after a successful stint, he's made a free agency move and landed with the Detroit Red Wings this summer.
Unfortunately for Holl, things haven't been going as well over there, as it was recently revealed that he is struggling to crack the teams blue line, and will likely serve as an extra for their opening game.
It's not the end of the world for the 31-year old, who is a fantastic leader off the ice, and it's likely he can play his way onto the roster, but for now, it appears to be a struggle for someone who became such a favourite in Toronto.