To drink: Scotch, Laphroaig, straight up, a triple, with a tall soda water on ice on the side.
A large Caesar salad with anchovies and homemade croutons, and extra anchovies on the side to have with the hot yeast rolls in the bread basket.
Surf & Turf
A Morton's porterhouse, medium, with a bit of extra char from just a bit of time under the salamander. (a big ribeye was a close second)
Lobster tails with lemon and butter
To drink: a Sprecher Black Bavarian Kulmbacher style beer.
A large baked potato with sour cream, butter, chives and candied-smoked-bacon pieces on top. (the bacon candy crumbles made with brown sugar and cayenne pepper)
Asparagus with hollandaise
Assorted mushrooms in butter - well done.
For dessert: a strong black coffee and maybe some anisette toast to dunk.
For a digestivo a warm double Frangelico in a snifter with a layer of cream floated on top
A cigar, maybe an Astral or a Punch Rothschild or an Avo (a figurado of some sort) and another scotch like the one above.
... maybe later that evening a Brioschi.