Update – The contract details are in on Tuesday morning: Wayne Simmonds comes in below the “buriable” cap threshold on a two-year, $900k AAV deal, taking the financial risk out of this.

Elliotte Friedman is reporting on Monday afternoon that Wayne Simmonds and the Maple Leafs are making progress towards a contract extension that would bring the 33-year-old Scarborough native back for a second season in Toronto.

Friedman later added in his 31 Thoughts column, “Nothing is done until it is done, but it sounds like Wayne Simmonds will be back in Toronto.”

Coming off of an extended offseason that afforded him an opportunity to fully recuperate and train after years of battling incessant injuries, the right winger started the 2020-21 season looking rejuvenated, tallying five goals in his first 12 games as a Leaf while playing 11:03 per night, including a role at the net front of a top power-play unit that was — it feels strange to say it now — absolutely flying in the early stages of the season. He also dropped the gloves three times in his first dozen games, including once against Ben Chiarot in the season opener that helped spark the team and another to cap off his two-goal game against Vancouver.

However, after a broken wrist in early February sidelined him for six weeks (on a fluke play where he took a puck to the wrist on a clearance by his own teammate), Simmonds finished with just five points in his final 33 games, including just one assist in seven playoff games.

There is no fan in the Toronto market who doesn’t enjoy the hometown angle, Simmonds’ personality and physicality, and his commitment to doing whatever it takes to win. The question is whether or not the Leafs are wise to return at least two of the three veterans that were staples in their bottom six last season — i.e. Simmonds and Spezza, with no word on Joe Thornton yet — rather than notably shaking up the mix in search of more speed, energy, and offense from the depth of their lineup.

If the Leafs can return Simmonds on a contract closer to the league minimum than last year’s $1.5 million figure and use him more in the 12/13 forward role — as in, the coaching staff is fully willing to sit him on nights when more pace, transition, and playmaking ability is called for down the lineup, including potentially in critical playoff games —   then it could start to make more sense to keep Simmonds’ veteran leadership and physicality around as a depth option. But the Leafs need to tread carefully here in terms of making any promises about roles.

Last year, the coaching staff appeared unwilling to sit either Thornton or Simmonds at any point — even for R&R purposes in meaningless games down the stretch of the regular season — and that’s something that can’t be the case again in 2021-22 if either is to return.

There was never a natural identify fit on a fourth line that included Simmonds and Spezza, and Simmonds’ ability to keep up in the top-nine wasn’t there to the point where he could play up the lineup for significant stretches of time. He provides a noteworthy net-front presence still on the power play, but on the balance of his 5v5 play, it’s hard to really justify bringing Simmonds back as a full-time regular on a similar $1.5 million contract to last season.

What is also interesting about Simmonds’ likely return: A lot of the media narratives after the disappointing playoff exit centered around whether the Leafs went “too far” on their additions of veteran players with size/physicality to the lineup this past season, but there were immediate indications the Leafs were not going to back away from this approach all that much in Brendan Shanahan’s presser after the season:

“Those elements I thought we had addressed over the offseason will continue to be important pillars for our team — defensive play, sticking up for each other, being able to play physically in games where we are tested that way.”

For now, we wait to see if the two sides can formally hash out a deal out and what the final terms will be.