To make the pork shoulderPreheat the oven to 350°F.
Season the roast with salt and pepper to taste.
Heat a large ovenproof stewing pan or large sauce pot over medium-high heat and brown the roast for 12 minutes, turning to brown on all sides.
Transfer the roast to a plate.
In the same sauce pot add the olive oil, fennel, carrot, and onions and cook for 10 to 15 minutes, or until the onions are lightly browned.
Add the tomatoes with the juices, garlic, and herbs and sauté for 5 minutes, then add the wine.
Simmer to reduce by half and then add the meat broth.
Place the pork roast in the liquid.
Cover the pot and place it in the oven.
Roast until the meat is fork-tender, about 2 hours, or stick the roast with a skewer.
If the meat is done, there will be no resistance as you push the skewer through the meat.
To make the garlic mashed potatoesMeanwhile, place the garlic on a baking sheet.
Sprinkle the olive oil over the garlic and season with salt and pepper to taste.
Cover with aluminum foil.
Roast the garlic for 1 hour, or until tender.
Let the garlic cool and grind it into a paste with a food processor.
Place the potatoes in a saucepan full of cold water and bring to a boil.
Cook for about 20 minutes, or until cooked through.
Drain and set aside.
In another saucepan, melt the butter over medium-low heat, then add the cream and heat until it comes to a boil.
Mix in the potatoes and garlic and mash to the desired consistency.
Season with salt to taste.
When meat is done, skim away any fat from the braising liquid that appears on the surface.
Test the consistency of the sauce by placing a spoonful on a plate.
If a thin liquid bleeds out, reduce it further.
The sauce will be quite thick.
Slice the roast, place the slices on the roasted garlic mashed potatoes, and cover the meat with the reduced sauce.