Wine-Braised Brisket with Tart Cherries

Ingredients

• 0.7 cup balsamic vinegar 
• 6 pound second-cut beef brisket 
• 10 servings pepper black freshly ground
• 8 ounces cherries dried
• 0.7 cup brown sugar dark packed
• 3 large garlic cloves finely chopped
• 10 servings kosher fine
• 2 cups chicken broth reduced-sodium
• 0.3 cup matzoh cake meal (see Cooks' notes)
• 2 cups pinot noir chocolate brownies 
• 1 pound shallots ; peeled
• 3 tablespoons vegetable oil 
• 2  star anise whole (see Cooks' notes)
• 2 pounds young peeled (not pre-cut variety)

Equipment

• bowl
• frying pan
• baking sheet
• oven
• whisk
• pot
• roasting pan
• aluminum foil
• stove
• cutting board

Directions

1. Heat oven to 350°F with rack in middle.
2. Whisk together matzoh meal with 1 tablespoon kosher salt (2 teaspoons fine) and 1/2 teaspoon pepper. Pat brisket dry and dredge in matzoh mixture, shaking off excess.
3. Set roasting pan across 2 burners and in it heat 3 tablespoons oil over medium-high heat until oil shimmers. Brown brisket (fat side down first if using first cut) on both sides, 3 to 5 minutes per side.
4. Transfer to a large platter or rimmed baking sheet.
5. If necessary, add remaining tablespoon oil, then reduce heat to medium, and cook shallots, turning occasionally, until they begin to brown, about 2 minutes.
6. Add garlic and cook, stirring, until fragrant, 1 minute.
7. Add wine and boil until liquid is reduced by half, then stir in chicken stock, cherries, sugar, balsamic vinegar, star anise, and 1 teaspoon kosher salt (1/2 teaspoon fine salt). Bring to a simmer and return brisket, fat side up, to pan. Cover pan tightly with heavy-duty foil or a double layer of regular foil, and braise in oven for 2 hours.
8. Meanwhile, blanch carrots in a 3-quart pot of well-salted boiling water.
9. Drain and transfer to a bowl of ice water to stop cooking.
10. Drain again and pat dry.
11. Add carrots to roasting pan (after meat has braised for 2 hours), then cover again tightly with foil, and continue to braise in oven, until meat is fork-tender, 1 to 1 1/2 hours more.
12. If serving soon, transfer meat to a cutting board and let it rest, loosely covered, 15 minutes, then slice meat across the grain. Skim off any excess fat from surface of sauce, then discard star anise, and season to taste with salt. Reheat sauce, then return sliced meat to sauce to reheat before serving.
13. Serve meat with sauce and carrots on a large deep platter. (If making brisket ahead, see Cooks' Notes.)
14. •You can easily make your own matzoh cake meal by finely grinding regular matzoh meal in a clean, electric coffee/spice grinder.•First-cut brisket with a single side of exterior fat is relatively lean, while second-cut is more evenly marbled throughout. While second-cut has more succulent, moister meat, either works well in this recipe.•Each star anise is composed of 8 petals, so if the star anise you buy has no complete stars, count out 16 petals.•Regular-size carrots can be substituted for the smaller variety. Use same weight indicated, and cut them diagonally into 1-inch-thick pieces before blanching.•Brisket, like all braised meats, improves in flavor if made at least 1 day ahead, if not 3 days ahead. Leave brisket whole and let cool in sauce, uncovered, before chilling, covered. When ready to serve, remove meat from sauce, and discard solidified fat from sauce. Slice meat across the grain while it's still cold (it will cut into neater slices), then reheat gently in sauce, in oven or on top of the stove.