Eyes on Isles' Michel Anderson wrote a little while back that the Ottawa Senators are looking for veterans to add to their young, skilled lineup. Bailey is exactly what they're looking for in a veteran with plenty of NHL experience and post-season success. The Senators' lineup is filled with young NHL talent, but with the exception of a few players, most haven't seen what success looks like at the NHL level and in the postseason.
What makes Bailey appealing to Ottawa is his 993 career NHL games and 50 points in 71 playoff games under his belt. Speaking of the playoffs, the Senators have missed the postseason now for five straight seasons, and Senators GM Pierre Dorian has been vocal about wanting to add a top-six winger in order to help push them back into the playoff picture.
"We talked about our own team, and where we see it, and where see our own team compared to those are contending for a Cup? Where will players be able to contribute and what will their roles be to help us to get to being a successful team. We looked at our holes and we ranked every pro player whether it’s in the NHL or AHL."- Pierre Dorian
Ottawa doesn't even meet the salary cap floor as of right now per CapFriendly, so they'll have plenty of money to work with this offseason. Bailey's $5 million cap hit would work out just fine for Dorian, making Ottawa a perfect fit for the veteran winger.