Look at the reaction when Matthews tried to wear #9 and Wuerffel tried wearing #7.
There's absolutely no way Winslow would get away with wearing #81, especially with Gibbs back. Monk is just too fresh in the minds of the fans, I have no doubt he would get booed off the field if he tried to wear #81. Especially with his perceived attitude problem, taking a legend's number would do nothing to squash those perceptions and would only throw fuel on the fire.
I don't know who it would be up to officially, but with Gibbs being the team president I'm sure he would at least have a say in matters like that.
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