Milano was a first round draft pick (16th overall) in 2014. After spending parts of six seasons with the Columbus Blue Jackets and their AHL affiliate Cleveland, he was traded to the Ducks in exchange for Devin Shore. Last season, he posted a career high 34 points over 66 games with Anaheim. Then, the Ducks elected not to extend a qualifying offer to Milano, allowing him to walk into unrestricted free agency.
Milano has played a career 197 NHL games, posting 81 points (36 goals & 45 assists) spanning over seven seasons.  He has battled serious injury throughout his career, which is likely part of the reason he has yet to find a suitable NHL contract.