max the dog

It's a tough problem but the solution could be to hit the middle and do both. Do it the Italian way, with gifts and kindness. Get the guys to caught up some money and slip it in a nice thank you card. It doesn't have to be a lot of money, maybe $100 each but not much more or you will appear to be rich. Just enough to get his attention. Attach the card to a nice bottle of whisky or a nice new jacket. When you visit him one day to drop off some venison or plow his drive offer him the gift and say how much the guys really appreciate his permission to hunt the land. Tell him how much the guys know how lucky they are to know a landowner like him and how carefull they are with his land. How you guys never drive across fields leaving ruts all over the place, never leave fences wide open, never cutting fences, or bringing alcohol onto his property and leaving garbage all over the place "like some other hunters do." That last part is important, make sure he knows how some other hunters can be abusive of permission and make an awfull mess of his place. If this goes well ask him for permission to hunt during the next season. He'll probably say yes. But if he seems hesitant tell him that if he ever was short of money you guys would be happy to make things legal and lease hunting rights to the land because at least he would be "leasing it to people he knows and trusts not to cause problems".
I don't care how much money some other hunters may dangle in front of him he will still prefer to lease to people he knows. You guys have proven yourself to be responsible hunters and that has value in itself. Make sure he knows it.

But if all that doesn't work you can always slip a severed horses head in bed with him.