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The legacy of Number 88 almost had a different ending in Dallas. Michael Irvin, the Cowboys legend and one of the pivotal players who shaped Dallas’ 90s dynasty, almost went to another team. As Irvin recently revealed on the Club Shay Shay podcast, there was a time when Jerry Jones was considering trading Irvin to another franchise. During that time, Irvin had seriously considered joining the Raiders. What makes it even more striking? Irvin’s deep admiration for the late Raiders owner Al Davis, a figure both revered and feared across the league.

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On the podcast, Shannon Sharpe made the statement: “Mike, you almost got traded to the Raiders.” As Irvin candidly replied, “I would have loved to go to the Raiders if I was going to get traded.” That was no casual remark. It reflected a genuine respect and a connection with a franchise that has long been the Cowboys’ fiercest rival. The pivot for Irvin would have been Al Davis. As he recalled, “You remember Al Davis? You know how he used to walk around when you were working out and always come by… He would watch you work out and say, ‘Boy, you work out like a Raider. So, you want to be a Raider? … For us, that was like Michael Corleone inviting you into the family.”

Al Davis, the legendary figure who shaped the Raiders into an iconic NFL brand through his relentless pursuit of championships and his instinct for spotting talent, had a presence that made players feel like they belonged to something special. But beyond admiration, Davis also played a crucial role for Michael Irvin behind the scenes.

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When Jones was still new as the Cowboys’ owner and considered trading Irvin, it was Davis who intervened. As Irvin recalled, “Al Davis was the one [who] told him cause he was new. Jerry was new. He said, ‘You don’t trade people like that. You should trust me, you don’t trade people like that.’” Davis’ voice carried weight, not just because of his success but because he understood player value on a level that sometimes eluded others. Naturally, Jerry listened, and that intervention kept Irvin in Dallas. But what if he hadn’t?

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Michael Irvin with the Raiders? The rivalry, respect, and reality.

If Michael Irvin had gone to the Raiders, the Cowboys’ dominance in the 90’s might have looked very different. Instead of being on the Dallas’ ‘Triplets’ alongside Troy Aikman and Emmitt Smith, Irvine would have been a key figure in a Raiders offense defined by grit and swagger under Davis’ leadership. The aura of the Raiders, built on toughness and rebellion, could have offered Irvin a different platform to shine, possibly reshaping the power dynamics in the AFC and NFC.

Irvin played for Dallas from 1988 through 1999. There have been no playoff battles between the Raiders and the Cowboys during that time. But in the regular season, they faced off three times. The Raiders lost twice, once in Week 8 of the 1992 season and the other in Week 12 of the 1995 season. The only Raiders win during that time was in Week 4 of the 1997 season. But if Irvin had lined up with the Raiders at the time, they might just have a 3-0 record to show for it. But Davis’ intervention ultimately helped Dallas.

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Davis, despite being a rival owner, was a mentor figure for many and commanded loyalty even outside his franchise. Irvin’s appreciation for Davis underscores how much influence the Raiders’ owner had as a football mind and personality. When Sharpe noted that they saw Davis all the time, Irvin laughed and added, “That mean you know he knows and he saying you one of them dawgs cause we only want dawgs over here. So he played that great man. I love Al, man. I loved Al.”

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Would the Cowboys' 90s dynasty have crumbled if Michael Irvin had joined the Raiders?

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This dynamic also exposes the clash between Jerry Jones and his players throughout his tenure. Jerry’s relationship with talent has been complicated, the Micah Parsons trade being only the latest in a long line of moves that raised eyebrows. But Irvin’s revelation of Davis’ role adds nuance, showing that sometimes a rival’s influence can sway decisions within a franchise. Both teams move forward in the present time. The Cowboys, under Jones’ steady if turbulent leadership, and the Raiders, trying to recapture Davis’ legacy in Las Vegas. Dallas will face off against the Raiders again in Week 11 this season. When we watch that clash, Irvin’s story will stand as a vivid chapter in their intertwined histories.

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Would the Cowboys' 90s dynasty have crumbled if Michael Irvin had joined the Raiders?

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