I think I found a good balance. I was seeing a lot of "win" animations for the offensive ball handlers (such as crossing back to another side to get into the lane) or simply dipping the shoulder to get past them.
Jeff Teague did this multiple times (3) on Kirk Hinrich (the crossing back animation and dipping his shoulder to speed past) to drive to the paint so this leads me to believe the threshold is a 35 point difference (Teague Ball-handling 95, Kirk On Ball D 60) for the offense to "win" 60% of the time.
Deng was even able to win with 80 ballhandling on Jenkins and Smith 55 On Ball D (Dipping shoulder animation). So 2 times he won with ballhandling.