Mn3,
How do you know it isn't rudder push or whatever the opposite of rudder tug would be?
It would only be "rudder push" if the working point of the rudders were before the pivot point of the rudderstock.
And that's very unlikely.
I would say to Bob: rake the mast to aft. Put an extra shackle in the fore-stay and adjust the shrouds accordingly.
And see how this works.