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Monday Mailbag – What would be a successful free agency period for the Oilers?

Happy Canada Day, Nation! I hope that if you’re reading this right now that you’ve already settled into day-off mode and that you just woke up from a nice sleep in. To those of you that are still stuck at work today, I hope you use this Canada Day-themed mailbag as a means to get yourself through these last hours before you get to go home and enjoy your life. As always, this feature depends on you guys and if you have a question for next week you can email it to me at baggedmilk@oilersnation.com or hit me up on Twitter at @jsbmbaggedmilk. Happy birthday, Canada!

Apr 18, 2019; Raleigh, NC, USA; Washington Capitals right wing Brett Connolly (10) skates against the Carolina Hurricanes in game four of the first round of the 2019 Stanley Cup Playoffs at PNC Arena. The Carolina Hurricanes defeated the Washington Capitals 2-1. Mandatory Credit: James Guillory-USA TODAY Sports

1) Trent asks – The mailbag will go up as free agency kicks off and I’m wondering what everyone thinks would be a successful day for the Oilers?

Jason Gregor:

If they can land a third line centre, preferably a right shot, two wingers and a backup goalie. If Ken Holland can move one of his Dman to free up some cap space would be an added bonus.

Robin Brownlee:

For me, going with Mike Smith and Koskinen still leaves goaltending as a question mark. I was hoping the first name on Ken Holland’s mind would be Petr Mrazek. I don’t see the need for a third-line centre being as pressing as many do — I think Jujhar Khaira could play there despite coming off a so-so season — but the Oilers could still use a low-cost fix in the middle. Need a cheap forward or two, the likes of Brandon Pirri or Brandon Yanev.

Tyler Yaremchuk:

I won’t say a successful day, but in the next few weeks, I’d like to see the Oilers add a goaltender, a middle-six winger, and a third line centre. Doesn’t have to all be in free agency, but they need to cross those three items off the list for me to consider this a successful offseason.

Christian Pagnani:

If they add a few wingers, another goaltender to challenge Koskinen, and depth on the right side of the defence.

Chris the former Intern:

I’m a simple man and will be satisfied to see one solid bottom six forward signed, and something to happen/change with our goaltending situation.

Baggedmilk:

Here’s my bet… I think the Oilers close out a deal with Brett Connolly and add another couple of depth players around in the league minimum mark. I’m also thinking that Petr Mrazek comes to town, but that might just be me really hoping that we don’t get Mike Smith.

2) Oiler fan in Van asks – With all of the rumours circulating around the Oilers at the draft, was anyone surprised that no moves got done or was a quiet weekend more or less what was expected?

Jason Gregor:

Not at all. I didn’t expect much from them on draft day. I thought this week Holland might have found a partner to offload one of Russell or Sekera, but I didn’t think there would be other trades.

Robin Brownlee:

I was a bit surprised. I thought Holland would be busier in the week leading into the draft, but you need a trading partner to get something done.

Tyler Yaremchuk:

I was very surprised. I know Ken Holland isn’t a very active GM, but usually, when a GM takes over for a new team we see them be a little more active. I’m surprised Holland didn’t do anything to clear out cap space or shape the team more to his liking. Now, he still has a lot of time this offseason to accomplish that, but I was still shocked at how quiet they were around the draft.

Christian Pagnani:

I was a bit surprised. I wasn’t expecting to not have any activity from the Oilers. I for sure thought there’d be one or two minor trades. Maybe a depth winger or goaltender.

Chris the former Intern:

Not sure what we were expecting with Ken Holland? He’s a patient man and I saw exactly what I expected to see in terms of amount of moves made.

Baggedmilk:

I thought that Kris Russell might get shipped out on draft weekend, so I guess, I’m a little bit surprised that it didn’t happen, but that tends to be how things go. Every year, there are always plenty of rumours surrounding this team and none of them seems to ever happen so that’s probably my fault for having expectations. Let’s see what this week has to hold.

3) Stephen asks – Based on the lack of cap space and difficulty to shed salary, I’m concerned that the Oilers will be going into next season with more or less the same roster. Realistically, how many new players do you see coming to town before the 2019-20 season gets going?

Jason Gregor:

I expect there will be 6-8 new faces from the end of last season. Some via free agency, some via organizational promotion and one trade before the start of the season.

Robin Brownlee:

It won’t be more or less the same roster. For starters, Sekera, Puljujarvi and Talbot are out (likewise Spooner, Manning etc). I see a chance for a young forward like Tyler Benson to stick. Likewise a young blueliner like Caleb Jones. Then, there’s changes to come in free agency, so it’s not status quo.

Tyler Yaremchuk:

As I said in my first answer, I think three is a safe number. A goalie, a winger, and a centre. If they manage to swing a deal (Benning for Brown or dump Russell) then it could go to four, but I can’t see more than four fresh faces on the team next season.

Christian Pagnani:

There are ways of clearing cap space and mediocre defenders with a lot of money are being moved. I believe there’d be a trade for Andrej Sekera or Kris Russell. There’s been almost no activity from the Oilers, so it’s hard to expect a bunch of activity just around July 1st. I’d expect 3-4 new players, which isn’t enough to make the playoffs.

Chris the former Intern:

I’m banking on a couple. It’s definitely a challenge but I think Holland has some good relationships with people around the league, hopefully, he can swing a couple of things in our favour.

Baggedmilk:

Ken Holland has mentioned a few times that he knows the roster needs upgrades so I’ll be patiently waiting to see how he makes that happen. As you mentioned in your question, the Oilers don’t really have a whole lot of space to play around and that’ll mean Old Dutch will have to get creative. Unfortunately, and I’m only guessing here, he’ll probably have to add sweeteners to any deal that involves moving out a contract so we’ll see how far he’ll go to get that done.

4) Krista asks – Seeing as the Oilers will need players to produce on value contracts, which prospect would you put your money on to crack the opening night roster?

Jason Gregor:

Caleb Jones followed closely by Tyler Benson. Both are really close.

Robin Brownlee:

Benson or Jones.

Tyler Yaremchuk:

Tyler Benson is my pick. He has some offensive skill, has proven he can succeed at the pro level, and the fact he could play wing or centre gives him a good chance to crack this team next season. I also see him as a player who could really benefit from playing with other skilled players. He can make plays and create chances if you put him with a good finisher, he could be a productive NHLer.

Christian Pagnani:

Caleb Jones and Tyler Benson make the team.

Chris the former Intern:

I’m counting on Bouchard getting another handful of games at least. Other than that, I think it’s too early to tell.

Baggedmilk:

I think Caleb Jones will be the first one to get called up and I believe he’ll do a good job with the promotion. After that, I hope Holland sticks to his word and keeps everyone in the minors until it’s clear that they’re ready for prime time. I know Benson had a very solid rookie season and a lot of the boys are calling his name for this question, but I’d like to see if he can keep the ball rolling in his sophomore season with the Condors.

5) Taylor asks – I’d love to know what everyone is getting up to for Canada Day? What is the perfect way to spend the day?

Jason Gregor:

I spend it with my wife and son and we go to our friend’s annual Canada Day Party. It is great. They block off the street and the kids play games while parents relax and visit. It is perfect.

Robin Brownlee:

Counting my lucky stars. Canada Day is our wedding anniversary.

Tyler Yaremchuk:

Assuming the weather holds up, I’d love to spend the whole day outside and just enjoying summer but I don’t get the day off. I’ll be doing a full day of free agency coverage on TSN 1260 then heading straight to West Edmonton Mall to call the opening day of the Brick Invitational Tournament. If you’re at the mall, stop by and say hi!

Christian Pagnani:

I’m going to grab a large iced coffee from Tim Hortons, make breakfast, then make my girlfriend follow the free agent activity with me.

Chris the former Intern:

I’ll be spending the long weekend in Kananaskis which I’m pumped for. I’ve never been a big Canada Day celebrator but I’ll probably try to get out and watch the fireworks somewhere.

Baggedmilk:

I’ll be right here bloggin! Then, when the NHL shenanigans start to settle down, I’ll be getting day drunk and going to watch the fireworks.

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