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Khalil Mack trade window slamming shut for Chicago Bears

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Realistically speaking, prying Khalil Mack away from the Oakland Raiders was always going to be a difficult proposition for the Chicago Bears (or anyone else for that matter).

With fifth-year options and franchise tags designed to ensure that a team doesn’t have to give up control of a prized possession, trading for an All-Pro edge rusher who is only 27 is about as far-fetched as walking into a storefront on Black Friday and walking out with that brand new TV without ever so much as having to throw an elbow. It’s technically possible but highly unlikely.

However, the idea that Mack’s holdout might put enough pressure on the Raiders to consider moving him fueled speculation that the trade window is open. With plenty of cap space and a few assets that might be of interest to Jon Gruden and Oakland, oddsmakers have decided that the Bears are second betting favorites to land Mack’s services, behind the Green Bay Packers but ahead of the Raiders.

That doesn’t mean the bookies know anything that we don’t. They’re simply trying to design a line that balances the books and allows them to take advantage of the books.

But if you’re a betting man and you’re looking to get your money in smart, go ahead and bet the Raiders to hold onto Mack through the trade deadline on Oct. 30. Because the latest reports are that Gruden and his front office are very quickly hanging up on teams calling to inquire about a trade.

Monday Morning Quarterback’s Albert Breer wrote on Tuesday that the Raiders have very quickly been telling people “No,” when they’ve asked about Mack. As a matter of principle, it makes sense. You don’t want to cave by rushing do trade a holdout and creating a public perception that you can be pushed around.

That doesn’t mean that a team can’t change their minds with a major offer (possibly one that includes two first-round picks like what the Packers potentially have to offer). But what it means for the Bears is that the asking price is probably well beyond their means at this point.

Mack is a game-changing player and those are hard to come by, so it’s easy to see why the Bears might be interested, especially with this franchise looking like it’s finally heading for the better. Unfortunately, the reality of this team is that they’re still most likely an offseason or two away from having the sort of roster health where a multi-year championship window will be open.

Giving up a first-round pick plus something else of value and then investing over $60 million in guarantees on a new contract for Mack simply won’t allow for the sort of flexibility needed to plug holes elsewhere on the roster in coming seasons. And financial flexibility has been the key for the Bears to turn this roster over in the first place.

As Dan Durkin of The Athletic noted, the Bears have starters under extremely reasonable contracts at quarterback, the tackle positions and on the edge. Those are the three most expensive positions in the NFL, so finding players who can outperform their cap hits allows for the construction of a more well-balanced roster.

Even if Mack makes a significant impact and accelerates the franchise’s timeline to contending for a Super Bowl, in all likelihood it would be the offseason heading into 2020 before the Bears had learned how to win as a group and were ready to compete at that level. That also happens to be the same offseason where you have to start negotiating a new deal for Mitchell Trubisky and start thinking about a long-term decision on Leonard Floyd.

Meanwhile, Mack would be heading into his age-30 season and would likely still be owed a boatload of money. While financial constraints alone wouldn’t preclude you from doing a deal, start considering the possibility that it would cost first-round picks in 2019 and 2020 to get a trade done and it gets hard to make it all add up.

Yes, Mack is one of the three most valuable defenders in football alongside J.J. Watt and Von Miller. But paying the premium of trading for those types of talents and paying for them is unsustainable.

The only two realistic methods of acquiring players like Mack are by draft or free agency, where it’s only draft capital or cap space you’re giving up at one time. Not both.

This is a league where the collective bargaining agreement demands you use the draft to collect contract-controlled talent. Even in a best-case scenario, Mack makes the Bears better but ultimately costs them the flexibility to make any improvements beyond that.

Worst-case scenario, he gets big money and begins to flame out, crippling the franchise and forcing them to tear it all down yet again.

If the Raiders budge and you can get a deal done for a first-round pick and an additional player or pick of fringe value, then you absolutely consider it. But if Oakland holds firm the Bears have to be okay with shutting the door on a trade for Khalil Mack.

Ryan Wooden is a full-time sports writer based in the Chicago suburbs. In addition to co-founding The Chicago Sports Column, he is a staffer for, a premium gambling and fantasy brand from CBS Interactive. Find him away from the computer (or don't) on some body of water or some golf course somewhere.