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At the risk of being a Killjoy - I can't help but believe that, generally speaking, the NFLPA are just shills for the guys - controlled opposition if you will - to give the illusion of balance.
Sure, we see guys like De Smith duking it out with Goodell every now and then with some highly publicized spat over player discipline or whatever - but that stuff is WWE -lite.
Look at the career path of Troy Vincent from NFLPA to Goodells right hand man - there were rumors that Vincent gave inside info to Goodell while he was still with the NFLPA.
The best litigators tend to go where the money is - and as rich as Tom and Gisele are - they are no match for the 32 owners + TV networks etc - so i'm sure Kessler is made out to be a giant-killer but he won't get anything the NFL isn't already prepared to concede.
If there is a reduction on Brady's ban, then its a reduction that Goodell et al already allowed for with the original sentencing.
Think about it; in the NFLPA goes 'scorched earth' on this and seriously damages the NFL - where does that leave an organisation that relies totally upon the NFL for its survival?
I think you should spend some more time looking in the background of Jeffrey Kessler. He's no shill.