After collecting Twitter questions last week, it’s time to tuck into some mailbag Q&A with the NHL offseason now possibly just hours away from officially getting underway.

Thanks to everyone who took the time to submit a question!

What do you think of the Wayne Simmonds signing?

First off, I’m glad that he signed for $900k this time around rather than the $1.5 million he signed for last offseason. For a Leafs team that needs every penny it can get at this point, the $600k can go towards upgrading another spot on their roster. Simmonds is a fourth-line player at this point, and given Toronto’s other big contracts, they can’t really afford to be paying $1.5 million to an average fourth-line winger.

I like having someone on the team who can fight when needed. The claims that the Leafs need more grit and physicality are largely overblown, but it’s nice that he can help to address that for just $900k. I really don’t think he’s close to the player that he used to be, but he can be this team’s Matt Martin.

I just hope that the Leafs scratch him come playoff time if he’s not one of their 12 best forwards. Obviously, there won’t be a problem if he plays well, but it’s tough to scratch a 32-year-old veteran who is not used to being a healthy scratch. His last playoff goal came in 2014 — it’s tough to accept the point that he’s the player who really elevates his game by scoring dirty goals come playoff time. He also didn’t have a primary assist this season, so I hope that he’s on the team’s worst offensive line.

I like Simmonds and I want him to do well. I have no issue with the contract itself, but he shouldn’t touch the top power-play unit this year and should be treated more along the lines of an enforcer. In other words, I hope that the Leafs will take him out of the lineup in the event that he really struggles.

A) Do you extend or trade Morgan Reilly this offseason? If you deal him, what do you get back? Established player(s) or just futures?

B) What would a Morgan Rielly trade look like in your eyes/what would/should the return be.

I would explore trade options for Rielly this offseason. He’s a good player — and they can always hang on to him if they get lowball offers — but I expect that there would be plenty of interest. I don’t want to give him a big extension, nor do I want him to walk for nothing next offseason. Given his reputation around the league, I fully expect that they could get a strong return.

Obviously, I’d be willing to take draft picks or prospects if the offer was good enough, but I think the preference should be on players who can help you immediately. Ideally, you can work with him to figure out a place where he would be willing to sign an extension and fetch more value as a result.

The Montreal Canadiens ended up with Nick Suzuki, Tomas Tatar, and a second-round pick for one season (plus an extension) of Max Pacioretty — that type of return would be the dream situation. Of course, if Rielly doesn’t want to extend elsewhere, his trade value likely won’t be quite as high.

I’d like a good NHL-ready prospect who carries plenty of years of control. Peyton Krebs would be a nice centerpiece from Vegas, for example. I’d be pretty open-minded about the return, though, as the Leafs are good enough to potentially justify trading for someone with one year of control such as Filip Forsberg, Tomas Hertl, or Johnny Gaudreau. However, if you do go with a rental, you still run into the problem of having the player potentially walk for nothing next offseason.

I think the good NHL-ready prospect approach is more likely to happen, but I’d consider just about any type of offer. I do think that I’d likely take the best offer available, but I suppose that there’s a chance that they only get lowball offers.

Rielly is certainly a good player — trading him would probably hurt this year’s roster, depending on the return — but it would set them up better for future success while allowing them to spend more to address their forward depth.

Should they trade Marner and Reilly and try to balance the depth and improve the third line? This could help move Engvall and Mikheyev to the fourth line.

I don’t think they going to trade Marner. Given that he’ll only make an average of $6.2 million per season in actual salary over the final four years, I do think that they should at least explore what they could get in return. I just don’t think that’s happening at this point, so I won’t spend too much time fussing over it.

I do think that trading Rielly is probably the right call, allowing them to improve the forward depth. In terms of Engvall and Mikheyev, I’d like them to be on a checking line that is (at least on paper) the team’s worst scoring line by a mile. I’d like to put Spezza with pretty good linemates and have them dominate against opposing third and fourth lines.

I’m also not 100% convinced that both Engvall and Mikheyev will be back — they’re who you move if you end up needing an extra $500k-$900k of cap space. I think that Simmonds should be on the fourth line as well, so I’d consider moving on from one of them.

A fourth line of Mikheyev-Engvall-Simmonds is fine, but they aren’t going to win many faceoffs or score much. I also think the Leafs would prefer to have Engvall on the wing come playoff time.

Nick Foligno, Mitch Marner, Toronto Maple Leafs vs. Winnipeg Jets
Photo by Darcy Finley/NHLI via Getty Images

What are realistic trade partners in a Rielly trade?

As mentioned above, Vegas seems like a good fit, given their track record of trading for good players and quickly extending them. Most players want to play in Vegas, and they’ve proven that they’re not scared to part with high-end young talent. They already have Alex Pietrangelo and Shea Theodore, but they could easily make the money work.

Calgary also seems like a great fit. Mark Giordano is 37 and might even be taken in the expansion draft, leaving the Flames in need of a long-term solution on the left side. Once Giordano’s contract expires next offseason, they won’t have a defenseman on their roster who carries a cap hit of more than $5 million. They could use a high-end offensive defenseman. Leafs fans were hoping for a Rielly-Tanev pairing for years — maybe that could be a good fit.

Another team that I’ll throw out there is the Philadelphia Flyers, who could use some help on defense. Provorov is their only defenseman who makes more than $5 million. Some sort of Travis Konecny trade could be fun, and I’d love to get James van Riemsdyk back if a team will help with the salary retention.

Ultimately, there are plenty of teams that could be interested in Rielly. If a team sees him as a true #1 defenseman, they could certainly make a big offer. Pittsburgh is interesting because of the Brian Burke connection, but they already have five defensemen who make over $4 million. They would have to get creative.

What do they do to fix this team? Do you think Foligno signs on a short-term discount given how badly things went? Do they find a way to sign Hamilton?

I think step one is to head into the playoffs with a good defense again. Let’s try that more than once!

Step two is to fix the power play, where I’d like to add another scoring threat. James van Riemsdyk is an elite net-front presence and could be a nice addition if they can find a team to retain part of his cap hit. Maybe stacking the team’s big four forwards on one unit will work next season, but I want them to be prepared in case it doesn’t. If you can find the right player for a fairly cheap price, I’d like a right-shooting forward with a good one-timer. Even someone like Emil Bemstrom could help them in this regard.

Essentially, if the power play is struggling to start the season, I’d have to consider putting Marner on his own unit and adding more of a shooting threat across from Matthews.

I think Foligno taking a slight discount is certainly possible, but that’s likely a family decision. Does he want to move his family to Toronto, especially if he’s going to be paid less? My guess is that he ends up back in Columbus, but I won’t rule it out completely. He would have to take a pretty big discount for me to be all that interested.

Signing Hamilton is probably a long shot. I’ll guess that they can’t find a way to sign him, but it would certainly make for an entertaining offseason if he became a Maple Leaf. This front office has certainly shown that they’re not afraid of making a big splash in the free-agent market.

The Leafs make you GM tomorrow, what are the first three transactions you make? Trades, re-signings, wait until the draft, and make a pick — whatever it is.

My first transaction would be at the LCBO, where I’d buy a nice bottle of wine to celebrate my new job as Leafs GM. There probably won’t be many signings until after the expansion draft, but I’d try to bring back Alex Galchenyuk and Zach Bogosian for the same price as last season.

If I did trade Rielly, it would probably be after the expansion draft, as many teams already have three defensemen that they want to protect. Once the expansion draft lists are out, I’d try to make a deal with Seattle, where the Kraken take a certain player and flip him to the Leafs for prospects.

I’d also consider moving on from Mikheyev, depending on what the offers are. I’d definitely call Arizona about Conor Garland. Oh, and as mentioned above, I would at least listen to offers on Marner.

Would you sign Jumbo for another year at league minimum?

If Thornton wants to return, I think they need to have an honest conversation with him first. If he’s not one of their top 12 forwards at any given time, he’s not playing. He’s certainly not used to being a healthy scratch, but I would tell him up front that it’s a real possibility. If he does return, he shouldn’t touch the top power-play unit, and he should be limited to a left-wing role across from Spezza. Given that he’ll be 42 next season, who knows if he even wants to keep playing?

I did like having him around last season, but Sheldon Keefe has to swear that he won’t be on PP1. Now that we know Simmonds and Spezza are coming back, it would be a bit strange if they signed Thornton and ran back almost the exact same group next season. Overall, I guess I’d be okay with signing him, but I’d at least have a few conditions.

Please explain what you think they should do to replace Hyman and why the answer is Pierre Engvall.

I like Engvall more than most, but I doubt he’ll ever be as good as Hyman. He’s also already on the team, so if he’s “replacing” Hyman, now you need someone to replace Engvall himself. I’m certainly open to giving him more ice time if he’s playing well — I like his size and skating combination — but I do think they need to make a big trade or signing if Hyman leaves.

Blake Coleman, Jaden Schwartz, and Brandon Saad are really the only natural replacements for Hyman in free agency. Who knows what they’ll cost, though? The Leafs may end up looking at cheaper options.

I could see the Leafs adding someone like Granlund or Tatar, but my guess is that Granlund ends up back in Nashville. Maybe Engvall plays outstanding and ends up in a top-six role, but I don’t think they’re handing him a top-six spot right now. I think they’ll end up with one of those other free-agent options, or perhaps swing a trade for someone like Tyler Bertuzzi.

How do the Leafs sign Dougie Hamilton? Who has to go for it to happen?

They’d have to offer him a seven-year deal around $8 million AAV. Unless there’s a massive blockbuster trade involving Marner, Morgan Rielly has to go in this scenario. You could probably find a way to keep Rielly for next season, but it’s tough to fathom that they could possibly re-sign him. Signing Hamilton is certainly worth exploring.

Lot of talk about adding LW and a 3C, and improving D (ideally with more PP shot threat). Are we under-prioritizing goaltending as fans? The final four teams had exceptional goaltending. Campbell looked great, but the Leafs need a 1b… Is there a true 1b to be had in free agency?

There’s plenty of 1B options to be had in free agency (I wrote about that here). I do think that some fans are probably under-prioritizing goaltending, but I can’t say that applies to everyone. Jack Campbell gave Leafs fans plenty of confidence this year, but injuries happen and no one would argue that he has the same track record as Rask or Vasilevskiy.

I could see them trying out a cheaper free agent option like Laurent Brossoit or Antti Raanta. If they struggle, they could always add someone at the deadline. If they give up a haul for someone like Kuemper, they’re less likely to make a change midseason, even if he struggles a bit. However, I do think they’ll try to spend $3 million or so on the second goalie rather than going with a $1 million flyer.

I do think they need a 1B rather than a true backup. I could see them making a trade, but given that the Leafs have to protect Campbell in the expansion draft, they’ll have to wait. Teams like Buffalo should be able to acquire a goalie before the expansion draft. Expect the list of options to shorten a bit over the next few weeks.

Toronto Maple Leafs vs. Winnipeg Jets, Jack Campbell
Photo: John Woods/Canadian Press

Is there any way the top three paid could put money in the pocket of a player as an advisor? (ie) Dougie Hamilton signs, and JT, Austin and Mitch pay him as advisor or something.

The short answer is no. Perhaps Hamilton will take a small hometown discount, but it won’t be because another player hired him as an advisor.

Who do you like for the Leafs to target with their second-round pick?

Someone who doesn’t get lonely very easily. The Leafs only have one pick in the first four rounds at the moment, so this player isn’t exactly going to have a bunch of friends to hang out with at rookie camp. Given the lack of picks, I’ll start by saying that I would 100% be attempting to trade down to acquire another pick or two. I also want to state that I’ve watched far less junior hockey in previous years, so keep in mind that there’s plenty of players who I haven’t seen.

The short answer is usually, “someone who I didn’t expect to be there.” It’s usually the smaller players that fall, and I wouldn’t be afraid to continue to take small players if they’re undervalued. Sean Behrens will probably be available there — I think he’s a bit underrated. Ville Koivunen was 91st on McKenzie’s list, which seems far too low.

I seem to like Jake Martin, Prokhor Poltapov, and Ryan Ufko more than most. Unfortunately, I’m far less confident in my draft opinions this year, as I just haven’t seen as many games. I’m far more excited for the NBA draft this year (I am fully on board the Jalen Green bandwagon).

What GM/Coach duo do you think has the most similar way of thinking and approaching hockey?

I have no idea. I feel like everyone would naturally want to say a good team, so the Buffalo Sabres probably aren’t a popular answer to this. Carolina always seems to draft well (by my rankings at least), and they make plenty of outside-of-the-box moves. The Leafs are also drafting very well as of late. I like the concept of having premium talent with a cheap fourth line.

There are some decisions that I question — such as what on earth they were doing on the power play — but I like the direction of the team overall.

Is there any doubt in your mind that once Auston Matthews’ current contract expires, that he’ll re-sign for the full eight-year max term with the Leafs? Should the Leafs pull a LAK/SJS & offer him the “C” while taking it from Tavares?

There’s no doubt in my mind that the Leafs will make a competitive offer, and I don’t get the sense that Matthews is itching to leave, either. I fully expect him to re-sign at this point, but I have no idea if it will be for the full eight-year max. It could potentially make sense for him to sign a five or six-year deal, bank on the cap going up further, and hit free agency again in his early 30s.

I think Tavares is a great captain, and I expect that the fans care more about this than Matthews does. I wouldn’t consider this for at least two years, but if Tavares’ play really drops off, maybe they’ll consider it then. I don’t think Leafs brass is spending any time thinking about this right now.

Who are your favourite bargain-bin UFAs that you think the Leafs should target this off-season?

To start, I’d really like to bring Galchenyuk back. Tomas Tatar also seems bound to get underpaid since he was a healthy scratch for much of the playoffs, but he’s a good player with a long history of matching up against opposing top lines. Nick Bonino is another player who grades out extremely well by the numbers and could end up being a bargain. This is always a tough question, of course, as it only takes one team to make a big offer for the player not to fall into the bargain bin category.

I like Danton Heinen for a Galchenyuk-type deal, assuming he doesn’t get a qualifying offer and hits free agency. Of course, the big question always comes down to price. The Leafs can’t afford to get into any sort of bidding war for depth players. I also like Derek Ryan assuming he’ll make somewhat close to the league minimum.