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1
Heat the oven to 325 degrees F and arrange a rack in the lower third.
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2
Pat the roast dry with paper towels and trim any excess fat or sinew.
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3
Season generously with salt and pepper; set aside.
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4
Heat the oil in a large, heavy-bottomed pot or Dutch oven over medium-high heat until shimmering.
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5
Add the roast and cook, turning occasionally, until its browned all over, about 15 to 20 minutes total.
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6
Transfer to a large plate and set aside.
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7
Meanwhile, peel and cut the carrots into large dice; set aside.
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8
Cut the celery and onions into large dice.
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9
Add the carrots, celery, and onions to the pot and season with salt and pepper.
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10
Cook, stirring occasionally, until the vegetables have softened and are just starting to brown, about 5 to 7 minutes.
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11
Add the wine, scrape up any browned bits from the bottom of the pot, and bring to a boil.
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12
Cook, stirring occasionally, until the wine is reduced by half, about 7 minutes.
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13
Meanwhile, peel any loose outer skins from the garlic head and cut off the top quarter to expose the cloves (reserve the top for another use).
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14
Add the broth or stock, vinegar, garlic head, thyme, bay leaves, and rosemary, stir to combine, and bring to a boil.
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15
Return the roast and any accumulated juices on the plate to the pot.
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16
Cover with a tightfitting lid and place in the oven.
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17
Cook, flipping the roast every hour, until the beef is fork tender, about 3 hours total.
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18
Meanwhile, make the gremolata.
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19
Peel, core, and cut the apples into small dice.
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20
Place the apples in a medium nonreactive bowl, add the parsley, olive oil, and zest, season with salt and pepper, and toss to combine.
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21
Taste and season with additional salt and pepper as needed, cover, and refrigerate.
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22
Remove and discard the herbs and garlic from the pot.
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23
Break the beef into large chunks, top with the gremolata, and serve with the sauce.
