He was drafted twice, claimed off waivers three times, and three times he found new homes via free agency.
His first team was close to home - from the Chicago suburb of Park Ridge to the 2002 Chicago Blackhawks
Watch: Youtube Video
The first player to score on him? Hall of Famer Paul Kariya.
The first time he won? Fourteen months later…in his 14th NHL start. Only five other goalies have waited longer. On that night he was 30-for-30 in a 7-0 win over Columbus.
Three years beyond, he was wearing No. 30 and capping off his first and only campaign in Rochester.
Anderson's next 10 seasons were all winning ones as a member of the Panthers, Avs, and Senators.
In 2013, he led the NHL in both goals against and save percentage
On Anderson's decade in Ottawa, GM Pierre Dorion said simply, "He's the best goalie we've ever had."
In the more than 7,000 days since his NHL debut, Anderson has been supported by 365 unique teammates so far.
But no relationship resonates quite like the one with his teammate for life.
Craig's wife Nicholle was diagnosed with cancer in the fall of 2016. Anderson took personal leaves during parts of that season, famously returning from the first one to post a 37-save shutout in Edmonton
His team came one goal shy of a trip to the Stanley Cup Final.
He was second to Pekka Rinne in playoff wins, but his earning of the Masterton Trophy was unanimous.
Watch: Youtube Video
…As was victory for their family - with Nicholle now cancer-free.