Most years around this time, we put together the Monday Morning Quarterback Money List. It’s always fun to compile, but I think it’s even more appropriate to have fun conversations like this right now. So, after missing last year’s edition, let’s delve into the 2020 list.

The rules are straightforward. I’ve got one player for every area on the field I’d covet the most if I were starting a team to win a championship this season.

Defensive end – Willie Jefferson, Winnipeg Blue Bombers

We usually start this at quarterback, so I thought I’d change it up a little bit and get things going on the defensive side of the ball. When it comes to an outside defensive lineman, it’s hard to look anywhere beyond Winnipeg’s Jefferson. The reigning CFL Most Outstanding Defensive Player is coming off the most dominant season of his career, which is saying something knowing what he had already accomplished.

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At six-foot-seven, and 248 pounds, Jefferson brings something completely unique every snap. On pure physical appearance, Jefferson looks more like a big linebacker than anything else. But as any offensive lineman in this league knows, Jefferson’s unmatched combination of strength and speed makes him the most difficult player to defend in the league. Having a size or weight advantage on Jefferson rarely matters, because he’s just too quick and powerful.

2019 saw Jefferson continue to dominate in his first year with Winnipeg. Despite seeing constant double teams, Jefferson finished the season with 12 sacks, six forced fumbles, a pair of recoveries, and an interception. Only Saskatchewan’s Charleston Hughes and Hamilton’s Ja’Gared Davis finished with more sacks, while Jefferson’s whopping forced fumble total was easily good for top spot. Oh, and Jefferson’s 16 pass knockdowns set a new all-time mark for defensive linemen, which just goes to show: there really is no one like him.

Defensive tackle – Dylan Wynn, Hamilton Tiger-Cats

This came down to two players: Wynn and Micah Johnson of the BC Lions, and they were close. Yes, Wynn is five years younger than Johnson, but that’s not what this all about and, as such, didn’t impact my thinking. Instead, this came down to the most recent viewings of both players. Wynn is coming off his best CFL season, while Johnson is coming off a down year with the Riders.

After two years in Toronto, Wynn broke out in a huge way in his first year with the Ticats. Wynn finished fourth in the CFL with 11 sacks to go along with 44 defensive tackles, while also establishing himself as a franchise cornerstone in Hamilton. Wynn was part of an elite defensive front four last season, but that shouldn’t take away from what he accomplished.

At six-foot-two and 283 pounds, Wynn is big and powerful, but possesses the speed and agility to make him slippery to contain. It’s true Wynn’s age didn’t come into play when choosing between him and Johnson, mainly because I think the latter still has plenty of dominant football left in him. However, at 26, I really do believe Wynn is just getting started.

A watchful eye

Football personnel across the league were going to have a close eye on this weekend’s NFL Draft to begin with. But, knowing the current situation around the world, that eye is going to be trained much more. Not only do front offices need to find out what Canadian prospects will end up in the NFL, they’ll also want to see the ins and outs of a totally virtual and remote draft.

Because of restrictions imposed to due to a worldwide pandemic, team facilities will remain closed when the NFL’s three-day event gets going Thursday night. As such, all 32 teams will be setting up virtual war rooms from numerous locations and drafting remotely when it’s their turn.

We’ve never seen something like this before, which is why you can bet any sports league with a draft in the next few months will be extremely paying close attention. That includes the CFL, with the 2020 CFL Draft a few days later on April 30. There’s a lot that can be learned from how things go south of the border.

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There are a ton of easy questions right off the hop. How smoothly do things go? How do teams, and the league, deal with inevitable technical difficulties? What works, and what doesn’t work, this weekend will give important lessons the CFL can learn prior to going down a similar road a few days later.

Physical distancing measures are still being enforced in Canada, which means working from home is the new normal for the time being. I’m curious to see how teams in both leagues deal with not being in the same room to make crucial decisions on a contentious selection or a big potential trade. Will it change things dramatically? Or not at all?

We’ll start to get answers to those questions starting Thursday, and of course, we’ll also get a much better idea of how the CFL Draft order will start to fall, too. The top two Canadian prospects look like locks to be selected in the NFL. That means Notre Dame receiver Chase Claypool and Oklahoma defensive lineman Neville Gallimore will fall way down the CFL board, if they’re selected at all.

What becomes really interesting, though, is watching players on the NFL bubble this weekend. Will top ranked offensive linemen like Carter O’Donnell (Alberta) or Thomas Jack-Kurdyla (Buffalo) be drafted? And if they don’t, will they sign priority contracts? The former outcome means an almost certain plummet down the CFL board, while the latter might only have a negligible effect.

The NFL Draft is always a fairly important day on the CFL calendar, mainly because of how it affects this league’s draft days later. This year, though, what happens over NFL Draft weekend feels even more important for reasons few of us could have foreseen.