To spell it out for those who are missing the double-entendre:
Wes Welker could stop wearing his uniform if he has a season-ending injury.
Wes Welker could also stop wearing his uniform if the Patriots lose Sunday.
Bart's playing the same plausible deniability game as Wes was, but with a more sinister subtext.
In Wes' case, the two possibilities (in each instance) were:
1) Heh heh. Foot. Heh heh, and
2) Figures of speech related to Pats' own performance.
In Scott's case, the two possibilities were:
1) Heh heh, Wes will wear street clothes because he will be golfing when the Pats lose, see what I did there? or
2) I will cripple Wes Welker.
This definitely qualifies as upping the ante. It's also thug-funny because he has exactly the same out that Welker does (How do you get that from what I said?)
And of course, it's not funny to the other team's fans, but what else is new?