Did you check how much current the tool was drawing with a clamp meter? That would tell you a lot. You could also have a weak breaker. I have seen both old and brand-new breakers that tripped well below their stated rating. I would suggest trying another extension cord, possibly a #10 cord. It used to amaze me on construction sites how some tools with the same plate ratings would run on 200+ feet of extension cords and others would trip the break at 100'.
Also, is this a GFCI or Arc-fault breaker? Both can cause issues with some electric motors, especially arc fault-breakers. If you have access to a circuit analyzer, you might find that there are issues with the extension cord or the branch circuit itself. A #12 cord, rated for 20-amps, is not going to perform up to its potential if it is connected to a 15-amp, #14 branch circuit.