The Caps have several key contributors set to hit unrestricted free agency, including Brett Connolly, Brooks Orpik, Carl Hagelin and Devante Smith-Pelly, while the likes of Jakub Vrana, Andre Burakovsky, Christian Djoos, Chandler Stephenson and Dmitrij Jaskin will be restricted free agents.
"I look at Brett Connolly. The amount of money he could probably get out there right now is a lot more, and is probably a lot more term, than they are willing to give him," said May.
"After what (Burakovsky) went through and no one made it a secret that he was on the trading block, he could be gone. I loved the way he played down the stretch. Devante Smith-Pelly, I'd be surprised if he's back after the season he had."
"And then on defense: is it time to say goodbye to Brooks Orpik? Jonas Siegenthaler played so well in those last few games that he played. And it's just a small sample, but you'd think that he's gonna garner the respect that he's deserved, that he would be playing opening night if he has a good training camp and shows up in shape."
"I think the team has to change their physical makeup," May continued. "They were tired at times this season, but at the same time, when they were winning, it looked a little too easy. They weren't as ugly, the games weren't as physical. They were almost too polite, with the exception of Wilson and Ovi all season long."
"I think they need to add some more grit and some more bite, and that means that some of the players that are on the roster will be replaced by players that play a more physical, a hungrier brand of hockey on a nightly basis."
And given that need for more physicality, May could see the Caps make a blockbuster move to try and get back to the top of the NHL mountain.
"I would not be surprised if they pull something major off, just for the fact there has to be a (physical) element on this team," May told the Junkies. "When you're watching the Stanley Cup playoffs every night, the games are gritty. They're crash and bang."
"You have to have a different chemical composition on this team in the future, because you want to get back to playing that way. Because that's essentially how they won the Stanley Cup was being a grittier team."
"They have to have everyone on board for that. So I think you need some more vinegar in the lineup, and the other part of it as well."