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The Raiders contacted the Bears before of free agency to inquire about a Khalil Mack reunion, according to sources.

Jon Gruden wants to win, and there have been occasions during the Raiders’ three non-winning seasons when he has been visibly unhappy.
He admitted to crying for three days after transferring former NFL defensive player of the year Khalil Mack to the Chicago Bears shortly before the start of his return season in 2018.The Raiders have had a clear need for a proven pass rusher since trading Mack to the Bears over three years ago, and when free agency started in March, they targeted and expected to acquire Yannick Ngakoue.
The Bears were dealing with serious salary-cap concerns, forcing them to release All-Pro cornerback Kyle Fuller and restructure other contracts, and the Raiders decided it was worth a risk.
The Bears were not interested, according to sources, and the Raiders moved ahead and signed Ngakoue to a two-year, $26 million contract. Raiders officials had no comment, since they don’t discuss about trade proposals given or took, even the most interesting ones.Gruden received fire from the media when he sold Mack for a slew of draft picks, including two first-rounders, nine days before the 2018 season began.