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One of the toughest things Indianapolis Colts owner Jim Irsay has had to stomach in his NFL tenure was watching quarterback Peyton Manning win another Super Bowl elsewhere. It was something that spawned an awkward verbal dance for Irsay over the past few years, as he struggled with the reality that Manning wouldn't retire as a Colt, and would wrap his career with a second Super Bowl ring that Irsay desperately wanted him to win in Indianapolis. This is something that Dallas Cowboys owner Jerry Jones will grapple with if Tony Romo doesn't retire this offseason.