dH knew this. Is why the lovely handling (on the ground as well as in the air) Chipmunk has a free castoring tail wheel.
Makes it a heck of a lot easier to manhandle it in and out of the hangar, too! The 'spring connected tail wheel' Citabria was right pain in this respect.
And of course with a FC tailwheel you can enjoy the hooliganism of 360s on the spot (OK, around the relevant main wheel), followed by the same the other way! Good way to teach anticipation timing needed to steer it on the ground (for turn reversal in the rapid 360s) using the rudder-operated brakes.