Heat oven to 250 degrees F.
Remove ham from bag, rinse and drain thoroughly.
Place ham, cut side down, in a roasting pan. Using a
small paring knife or clean utility knife set to the
smallest blade setting, score the ham from bottom to
top, spiraling clockwise as you cut. (If you're using a
paring knife, be careful to only cut through the skin
and first few layers of fat). Rotate the ham after each
cut so that the scores are no more than 2-inches across.
Once you've made it all the way around, move the knife
to the other hand and repeat, spiraling counter
clockwise. The aim is to create a diamond pattern all
over the ham. (Don't worry too much about precision
Tent the ham with heavy duty foil, insert a
thermometer, and cook for 3 to 4 hours or until the
internal temperature at the deepest part of the meat
registers 130 degrees F.
Remove and use tongs to pull away the diamonds of
skin and any sheets of fat that come off with them.
Heat oven to 350 degrees F.
Dab dry with paper towels, then brush on a liberal
coat of mustard, using either a basting brush or a clean
paint brush (clean as in never-touched paint). Sprinkle
on brown sugar, packing loosely as you go until the ham
is coated. Spritz this layer lightly with bourbon, then
loosely pack on as much of the crushed cookies as you
Insert the thermometer (don't use the old hole) and
return to the oven (uncovered). Cook until interior
temperature reaches 140 degrees F, approximately 1 hour.
Let the roast rest for 1/2 hour before carving.
*Cook's note: A city ham is basically any brined ham
that's packed in a plastic bag, held in a refrigerated
case and marked "ready to cook", "partially cooked" or
"ready to serve". Better city hams are also labeled "ham
in natural juices".