With Brad Treliving going on to make a trade before the March 7 deadline, he's got a lot of homework to do in order to make sure everything is in place before any rash decisions are made.
The team has enjoyed a bevy of success this season, sitting first in the Atlantic and only two points off of Washington for top spot in the East. But one of their glaring holes has been offense and defense on their third line, though it's shown flashes of brilliance is quite inconsistent.
Come playoff time, Toronto is going to need everybody pitching in but there could be a piece added via the trade market that could instantly add a postseason punch; they just need to ask a heated rival for his services.
Asking one of your most heated rivals not only of the last two decades but one that has been around forever is a big ask, but Toronto has the pieces necessary in order to get a deal done for Frederic.
Standing 6'3, 220 pounds he's a huge body that adds another behemoth to Craig Berube and Brad Treliving's vision.
He's a center which is a huge plus but he also is a free agent at season's end, so unless the team is convinced they can offer him an extension, it could be a bit risky.
This season Frederic has struggled, with only six goals and six assists in 44 games but had an 18-goal, 40-point season last year and looked like he was starting to break out.
He's still only 26 as well, so Toronto would be able to get him in his prime if they are able to keep him around.
He had five points in last year's playoffs and scored three times in Boston's first round series against the Maple Leafs, so there's no doubt they'd like to have him on their side this time around.
Boston is also right in the thick of a playoff race and might be hesitant to make any roster moves unless things completely implode and Boston freefalls in the standings.
He is cheap though at $2.3M so if Toronto wanted to they could put a package together including Nick Robertson or Pontus Holmberg, plus a low pick could be enough to convince GM Cam Neely to part with his power forward.
It's going to take a lot for the right player to come to the Maple Leafs and make an impact. But if Toronto could snag him from the Bruins, it could be the difference maker come the postseason.