Over the span of a year, the Oakland Raiders have parted ways with some of the league's best: edge-rusher Khalil Mack and wide receiver Antonio Brown. In doing so, Jon Gruden cracked jokes on Saturday in the aftermath of Brown's stunning release.

“At least I got to meet Antonio,” he said, per Matt Schneidman of The Athletic. “I never got to meet Khalil.”

The reasons for parting ways with Mack and Brown differ wildly. Mack was wanting a contract extension that the Raiders wouldn't give him. After holding out, Oakland decided to get assets for the All-Pro, by trading him to the Chicago Bears for a massive haul that included two first-round selections in back-to-back years.

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Brown, on the other hand, was acquired by the Raiders in a trade with the Pittsburgh Steelers. They would go on to regret that. After freezing his feet in a cryogenic chamber, filing two grievances with the NFL over a dispute for his helmet, missing training camp, getting fined, fighting with the general manager, getting suspended, getting unsuspended, and posting a video of a private call with Gruden, the Raiders released him and voided his contract due to conduct detrimental to the team.

Mack's departure from Oakland was far from as dramatic as Brown's. While Mack did what was in his best interests financially, Brown acted up in all facets and wore his time thin with those donning black and silver before he could play a snap for the Raiders. Now, he's looking for a new team.

But at least Gruden got to meet him, unlike the current Chicago Bears superstar.