That's different for everybody, considering that it's not scientifically proven to do anything for preventing injury or improving dynamic flexibility then I'd say do it as little as possible. It feels good and that's about it. It decreases power if done before sport as well, that's well documented. It may help in slower, concentric movement performance due to less energy loss through hysteresis but that's not really relevant to anyone who is playing a sport that requires speed and RFD.
I don't know enough about Judo to really comment but you need to remember that dynamic flexibility has no relationship to passive flexibility, contrary to many peoples beliefs. You can kick someone in their head no problem and then not be able to touch your toes. You can be powerful and flexible. If you're the wrong type of flexible at the wrong places then that's when it can decrease performance.
Curiosity got the best of me and I just googled 'Wladimir Klitschko bench press' and according to 'Wiki answers' it looks like CHEF himself is quoted saying Wlad benches 395 for 4 reps. 275 for 20 reps. Not sure if this quote is accurate though.