No. 1: Let Him Walk
The Toronto Maple Leafs have been known to let players walk into free agency over the past few years. Whether it was Tyler Bozak, James van Riemsdyk, Freddie Andersen, Nick Foligno or Zach Hyman, the team hasn’t had any issue with seeing someone leave without receiving compensation.
The idea of trading a good player who’s going to be a UFA, just to receive a draft pick, is a silly idea, if you’re a good team. A second-round pick is not as valuable as the star player you’d be trading off of your roster heading into the playoffs. People always say “you lost him for nothing” but actually you chose to take his post trade-deadline performance instead of the future compensation. If you have a chance to win a Stanley Cup it’s a reasonable trade off for any team to make.
Rielly is an important piece to Toronto’s blue-line and it wouldn’t be a terrible idea to let the 2021-22 season play out and let him walk to free agency.
Also, by letting him walk into free agency, it doesn’t technically mean he won’t be able to return, or you may not want him to return.
Just look at the Freddie Andersen situation as an example. Toronto could have signed him to an extension the year prior, but they let the season play out and it worked out in their favor. Andersen played his way out of a contract and it turned into a smart move to let him walk.
Everyone knows the type of player that Rielly is, so it’s not likely that his AAV is going to skyrocket in one season. Therefore, playing the season out before making a decision could be a smart move, in case of injury or a huge dip in production.