Pork Shoulder Roast with Figs, Garlic, and Pinot Noir

Ingredients

• 0.5 teaspoon anise seeds 
• 0.5 tsp pepper black freshly ground
• 10 oz mission figs dried halved lengthwise
• 2 tablespoons thyme leaves fresh chopped
• 8  garlic cloves peeled cut into large slivers
• 1.5 tsp kosher salt 
• 3 tablespoons olive oil 
• 750 ml pinot noir chocolate brownies divided
• 3.5 lbs boned pork shoulder roast (butt)
• 1 tablespoon sugar 

Equipment

• bowl
• frying pan
• sauce pan
• oven
• knife
• baking pan
• wooden spoon
• aluminum foil
• cutting board
• gravy boat
• kitchen twine

Directions

1. Put figs, sugar, anise, 1 tbsp. thyme, and 1 cup wine in a medium saucepan. Cover and bring to a boil over high heat. Reduce heat and simmer until figs are just tender when pierced, 10 to 12 minutes.
2. Let cool.
3. With a small, sharp knife, make 16 evenly spaced lengthwise cuts into roast, each cut about 1 in. long and 1 in. deep. Insert a garlic sliver, then a fig half into each cut, closing meat over figs; make cuts a little bigger if needed. Set aside remaining garlic and figs and their liquid.
4. Preheat oven to 32
5. Using kitchen twine, tie pork crosswise at about 1 1/2-in. intervals and lengthwise twice to form a neat roast. In a small bowl, combine 1 tbsp. thyme, 1 1/2 tsp. salt, 1/2 tsp. pepper, and the oil. Rub all over roast.
6. Heat a 12-in. frying pan over medium-high heat. Brown pork all over, turning as needed, 8 to 10 minutes total; adjust heat if needed to keep meat from scorching.
7. Transfer pork fat side up to a 9- by 13-in. baking pan.
8. Reduce heat to medium.
9. Add reserved garlic to frying pan; cook, stirring often, until light golden, about 1 minute.
10. Pour in remaining wine from bottle and bring to a boil, scraping up browned bits with a wooden spoon.
11. Pour mixture over pork and cover tightly with foil.
12. Bake pork until almost tender when pierced, 2 1/2 hours. Stir reserved fig mixture into pan juices; bake, covered, until meat is tender, 15 to 20 minutes more.
13. Spoon pan juices over pork to moisten, then transfer meat to a cutting board and tent loosely with foil. Skim fat from pan juices.
14. Pour juices with figs into a large frying pan and boil over high heat until reduced to 2 cups, about 5 minutes. Stir in 1/2 tsp. thyme. Taste and season with lemon juice and more salt and pepper if you like.
15. Pour into a gravy boat.
16. Remove twine from pork, then cut meat crosswise into thick slices.
17. Garnish with thyme sprigs and serve with sauce.
18. Make ahead: Prepare through step 3 and chill airtight up to 1 day.