Since your horse drives, he's already 3/4
of the way trained to tail. All you need to do get out your
long-lines, get your driving whip, and take him long-lining down the
road. Once he's marching forward just grab the end of his tail.
Don't pull it... just hold it, and cluck to him to keep him going forward
while your reins make sure he's staying straight. (You can hold
the lines and whip in one hand, to leave the other free to hold the
tail) He'll be wondering what you're doing at first, but just cluck to him
smartly and keep him marching forward. If he's doing fine, and marching
along confidently, commence to swing his tail slightly from side to side as you
walk. After a minute to so, he'll start ignoring your silliness, and
disregard what's happening to his tail.
You will be best to keep him on dual long-lines
until your hanging onto his tail become so routine he doesn't twist an ear when
you pick it up or swing it. Once he's achieved this level of confidence,
start applying backward pressure to his tail as you cluck to keep him
marching. Don't switch to a single long line until he stops and starts at
your verbal command while facing forward down the road, his tail in your
grasp. Use the same cues as when you drive him -- it's not much different
for him to pull via his tail, or via his chest, as long as the commands are the
same. You want him listening to your voice when you tail, not relying
upon a tug on a line which can accidentally turn him around.
It's great fun to have a horse that will tail,
and you'll save more of your horse's reserves by getting off and
tailing on steep slope than you'll ever realize --sometimes enough to
make the critical difference between a middle-of-the-road completion... or a top
ten placing. :-)