Jon Gruden And Khalil Mack’s Agent Both Have A History Of Navigating Player Holdouts

It’s down to just two weeks before the Raiders season opener and the greatest uncertainty on Jon Gruden’s roster still involves his self-proclaimed best player on the team. Most believe Khalil Mack will show up in time to face the Rams, but with so many conflicting reports swirling around, it’s hard to get a feeling for how his situation is going to play out.

Mack will presumably miss the final preseason game and should he decide to miss regular season games, it will cost him just under $815,000 per game. The Raiders will almost certainly forgive Mack’s preseason fines, as they did with Donald Penn, but missed game checks would be real money lost.

Based on the money, odds are that Mack will show up. He just doesn’t gain enough leverage by missing real games. Mack is represented by super agent Joel Segal, who has a history of holding out players, but none into the regular season – former Titans running back Chris Johnson (with Segal at the time) came close, but ended up getting a new deal in the first week of September.

On the other side of Mack’s holdout, of course, is Jon Gruden, who presided over exactly one holdout in his career and former agent Joel Corry, who was representing the player, offered an interesting story about dealing with Gruden at the time:

“As an agent, I was involved in two lengthy holdouts with wide receivers Jimmy Smith and Keenan McCardell. My experiences give me a certain appreciation about contract disputes. Smith’s 38-day holdout in 2002 resulted with him getting a new contract from the Jaguars at the end of the preseason. McCardell’s dispute with the Buccaneers in 2004 lasted 82 days before he was dealt to the Chargers right before the trading deadline. His situation may be a little more instructive since it was the last time a player coached by Jon Gruden engaged in a holdout prior to Mack this year.

McCardell’s holdout got so acrimonious that forcing a trade became the priority over a new contract. We had McCardell fly to Tampa about a week before the trading deadline for an impromptu meeting with Gruden. McCardell was instructed to be extremely confrontational, which was out of character for him. We thought that approach might help accomplish our new objective since a former colleague of Gruden’s told me he hated confrontation.

We wanted Gruden to get a taste of what life might be like if a disgruntled McCardell came back. I suspect the meeting helped spur McCardell’s trade. Gruden couldn’t have been looking forward to an unhappy McCardell eventually returning, after Gruden got fed up enough with Keyshawn Johnson the year before to give him a paid leave of absence over the final six games of the 2003 season for being a disruptive influence.”

Maybe Gruden won’t be as stubborn with a former MVP, but it’s interesting to hear that he doesn’t like conflict (noted for future reference). It’s hard to imagine Mack coming back and souring the locker room, but if he wanted a quicker way into a new deal (albeit with a new team), history says there might be a way.

Some would say that Mack’s negotiations are typical for a contract of this size and that may be true, but it’s worth noting that Derek Carr signed a record deal a year ago without anywhere near this level of frustration. There’s still something about Mack’s situation that doesn’t add up to a good reason for why the standoff has lasted this long. But all will be well that ends well and the smart people involved still have about two weeks to get something figured out.

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