The rule of thumb is this:

Scenario 1:
If the security screening line is long, chances are the TSA supervisor is "working" along side of the other screeners to assist with getting pax through faster.........if this is the case, the run-of-the-mill TSA guy will likely pull you for having the liquids / gells greater than 3 oz so that he can impress the "boss".

Scenario 2:
If the line is short, the TSA supervisor is probably at starbucks counting coins to buy a Latte' while the run-of-the-mill TSA guy wishes he were at Starbucks too. In this case, he could give a rip if you carried a keg of Coors Light through security while wearing your straw hat, cut-off jeans, hawaiian shirt and crew badge!

Hope this helps!