Dallas City News

On September 1st, 2018, the Raiders traded edge rusher Khalil Mack, the fifth-overall pick in the 2014 draft, to the Bears for two first-round picks and change. The Bears promptly made Mack the highest-paid defender in the league, signing him to a record-setting six-year, $141 million extension.

At the time of the trade

• Mack had been with the Raiders for four years
• Mack was a three-time Pro Bowler and two-time All Pro
• Mack had recorded 40.5 sacks over four seasons, including three consecutive double-digit sack seasons
• The Raiders had exercised the fifth-year option on Mack’s contract and could have used a franchise tag on Mack in 2019
• Mack had sat out the entire offseason, missing out on the Raiders’ voluntary offseason training program, the team’s mandatory minicamp, and the entirety of training camp in an effort to secure a long-term, top-of-the-market deal.

The Raiders gave up Khalil Mack, a 2020 second-round pick, and a conditional 2020 fifth-round pick to the Bears for two first-round picks (2019 & 2020), a 2019 sixth-round pick, and a 2020 third-round pick.

Raiders general manager at the time, Reggie McKenzie, said the team had tried to meet Mack’s demands but ultimately wasn’t able to.

“We wanted, all of us — Gruden, myself, everybody in the organization — wanted Khalil to be a Raider. That’s not an issue at all. We presented him with an offer and we got that counter back and talked about it with him … and it just, what they were demanding, it just wasn’t going to work at that time … it didn’t work out in the end … we weren’t close. We presented prior to the start of the league year … Khalil got a great deal,” he said.

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Fast forward to 2024 and Micah Parsons is entering his fourth year with the Cowboys.

After three years

• Parsons is a three-time Pro Bowler and two-time All Pro
• Parsons has recorded 40.5 sacks over three seasons, including three consecutive double-digit sack seasons
• The Cowboys exercised the fifth-year option on Parsons’ contract and could use a franchise tag on Parsons in 2026
• Stephen Jones said at the training camp press conference that Micah Parsons wants to become the highest paid non-quarterback in football, which would be over $35M per season.

Parsons is at camp with the Cowboys this year, so that’s where the similarities with Mack end, but barring a contract extension, a holdout next year seems quite likely for a player who likes to say that there’s a business side to the game.

And perhaps now is a good time for the Cowboys to explain what that business could look like for him, and should explain to him that he has two options:

1. Sign a contract extension with the Cowboys that makes him the highest-paid defender in the league, but with some significant concessions to the Cowboys in terms of length of contract.
2. Get traded after the 2024 season to a team willing to fork over two first-round picks for the right to make Parsons the highest-paid defender in the league. Oh, and make sure to play at a DPOY-level in 2024 for the Cowboys in order to secure that top-of-the-market contract somewhere else next year.

The Cowboys will ideally want a six-year extension (though they may be okay with five) that kicks in after the 2024 season. This will allow the team to eat some of the cap hit of the contract already in 2024, and then have two more years at the end that they can push cap money to with contract restructures in 2025 and 2026.

Parsons gets a $35 million per year deal, can call himself the highest-paid player in the NFL (for a few months, maybe), and secures generational wealth for him and his family. The alternative of course is to get shipped out of Dallas in a trade to the highest bidder after the 2024 season.

Which deal is the better deal, and for which party? Hard to answer up front, but let’s go back to the Khalil Mack trade.

In Mack’s four years in Oakland, they were 0-1 in the playoffs, in his four years in Chicago, they were 0-2, but at least made the playoffs twice. Hard to tell from a distance, but Mack may not have been “that one missing piece” for either team, though each team’s record after Mack left is telling: The Raiders went 4–12 the season after trading Mack, and the Bears were 3–14 in 2022 after trading Mack to the Chargers.

And the four draft picks Oakland got? Didn’t amount to all that much either. Here’s a look at the Approximate Value (for four years) for each pick and player involved in the trade:

Looks like Chicago came out slightly ahead, though that AV of 67 isn’t particularly much. Consider that Micah Parsons alone has an AV of 52 in just three years, while CeeDee Lamb has 53 in four.

The Raiders traded away a generational talent in Khalil Mack because they couldn’t or didn’t want to pay him. The odds of drafting another generational talent like that, even with two first-round picks, are not good.

And ultimately, that’s the question the Cowboys must answer: Two extra first-round picks sound great on paper, but are they enough to replace a generational talent? What if you end up with a Taco Charlton and a Morris Claiborne for your efforts? You’ll have lost a generational player and gained some… cap space. But cap space doesn’t win championships.

Over to you: Would you trade Parsons for a pair of first-round picks after the 2024 season?