Should Brad Treliving go full heel in Toronto and add this polarizing free agent defenseman?

The transformation that the team has undergone this summer is certainly intriguing, but there's still room for an addition or two to make the team even more unlikeable to the opposition. There's one player, in particular, who may even tick off some of the fans, but one who could undoubtedly help on the ice.

Tony DeAngelo is a household name in the NHL and not for any of the right reasons. Whether it's expressing himself a little too freely in the locker room or on social media or fighting with his own teammates after a game, DeAngelo has often been viewed as a "problem child" within the organizations that he has played. Make no mistake about it, signing him to a deal would come with a great number of risks, especially with the spotlight being what it is in Toronto.

Now, I'm not a fan of DeAngelo the person. DeAngelo the player, however.. the skill is undeniable. "Character issues" don't even begin to describe DeAngelo, but he does have two 50+ point seasons under his belt and is coming off of a 42-point campaign on a downright awful Philadelphia Flyers team last season. Also, if the Leafs want to build that identity of having "snot, piss and vinegar", DeAngelo has plenty of that. He'll stick up for his teammates and while he's not a high-volume hitter, he will play the body and he will drop the gloves as well.

We know that the Carolina Hurricanes tried to swing a trade with the Flyers to re-acquire DeAngelo earlier this summer, but that the league had blocked the trade, as Philly was trying to retain money on him to send him back to Carolina. Per the CBA, such a move would have circumvented the salary cap, as DeAngelo had played for the Canes just one year prior. However, DeAngelo has now been a free agent for multiple days and has not inked a deal with Carolina, which could mean that he's exploring other options and seeing what's out there for him on the open market before making a decision.

The 27-year-old enjoyed arguably the best season of his career in 2021-22 in Carolina, posting 51 points in 64 games and posting a +30 plus/minus rating. He also notched 10 points in 14 playoff games for the Canes. DeAngelo plays a premium position as a right-shot defender and he is very productive at the position as well, having racked up 45 goals and 199 points in 340 games.

Honestly, there's not a scenario in which I'd personally entertain the idea of bringing DeAngelo in if I was Brad Treliving, but Treliving does have the opportunity to go after a pretty solid offensive blueliner if he does choose to ignore the character issues and focus purely on the hockey. The questions are, will Treliving consider it? Would DeAngelo consider playing in Toronto? And, would the fans accept him? There were perceived character issues with both Bertuzzi and Domi and Treliving signed them without hesitation, so I wouldn't rule out the idea that he could pursue a deal for DeAngelo, but with Bertuzzi's issues being mostly related to the COVID vaccine and with Domi's issues being mostly limited to comments he had made many years ago as a young player on social media, I suppose there is some leeway there. However, with DeAngelo's many indiscretions being so recent, I'd imagine that weighing the pros and cons there would be a little different.

At this point, the Leafs have not been linked to DeAngelo, nor would I expect them to be. But, if Brad Treliving wants to go full heel this summer and inject some chaos, signing Tony D would certainly help to achieve that.