Braised Brisket with Red Wine & Prunes

the quintessential holiday meat

Despite having a great weekend, I am now sick as a dog. Not only do I have what feels like some kind of sinus infection, I feel like I have a slight fever, too. Thanks, world. Great. Juuuuust great. I suppose it was almost worth it. I cooked a brisket, had some friends over to eat said brisket, went to Prospect Park to enjoy the gorgeous weather, ate delicious Murray’s cheese and meats, had dinner at Walter Foods, and watched what was probably my favorite episode of Louie ever (yep, so good that it makes the weekend recap – congratulations to Louis C.K. on both this VIP mention and on his two Emmys). Still, though, being sick when it’s beautiful outside is the worst. I guess that’s why I’ve tried to deny it for the past few days, pushing myself a bit more than I probably should have. That’s why when I left for work this morning, I put on my prescription sunglasses on and left my regular glasses behind, so I got to look like I was out partying all night instead of sneezing and coughing as quietly as possible so that I could pay attention to Boardwalk Empire. At least I was able to come home a bit early today, so here I am, on the couch, in my pajamas, drinking disgusting but hopefully healing green juice (made with kale, AKA my mortal enemy) and watching TV.

Braised Brisket with Red Wine & Prunes

Anyway, this brisket ruled. The recipe comes from The Mile End Deli Cookbook, which is from, you guessed it, Mile End Deli in Brooklyn. Their food is life changing, I kid you not. I dream of their smoked meat sandwich and of their beautifully bright red housemade lox. I get way too excited when I know I’ll be eating there soon, so when my pre-ordered (duh) copy of their book finally arrived in the mail, I couldn’t wait to crack it open and start using the recipes within. First up, of course, in honor of the holidays, is this Braised Brisket with Red Wine and Prunes. I scored a 6-pound brisket recently, so I cooked this up and had a few friends over to enjoy it with me. The meat turned out beautifully tender and absolutely delicious, if I do say so myself, and despite having eight people tear into it this past weekend, we still have enough leftovers for a meal or two this week. The method couldn’t be easier – just saute some veggies, reduce your sauce, braise, and serve. I will be posting some of the sides that went along with this masterpiece later on in the week (not to mention the dessert – oh, the dessert – which is also from this book), but for now, I hope you are inspired by the cooler weather and reasonably priced brisket that is to be found around this time of year to make this yourself sometime in the near future.

Braised Brisket with Red Wine & Prunes
Everyone enjoying the brisket this past weekend.

Braised Brisket with Red Wine & Prunes
Then playing some Cards Against Humanity.

Braised Brisket with Red Wine & PrunesBraised Brisket with Red Wine & Prunes
Prospect Park on Sunday.

Braised Brisket with Red Wine & PrunesBraised Brisket with Red Wine & PrunesBraised Brisket with Red Wine & Prunes
Handsome Kramer.

Braised Brisket with Red Wine & Prunes
Picnic times.

Braised Brisket with Red Wine & PrunesBraised Brisket with Red Wine & PrunesBraised Brisket with Red Wine & PrunesBraised Brisket with Red Wine & Prunes
Step 1: Admire your brisket. Give it a name and show it some respect. Then rub salt, pepper, and red pepper flakes all over it.

Braised Brisket with Red Wine & Prunes
Sear it on each side until well browned.

Braised Brisket with Red Wine & Prunes
Then go ahead and star browning your onions.

Braised Brisket with Red Wine & Prunes
Add in your red wine, garlic, and red wine vinegar. Cook until the mixture in the pan is almost dry, then add in the tomatoes, brown sugar, and stock.

Braised Brisket with Red Wine & Prunes
After you’ve added the vegetables over the brisket in the roasting pan, add in the onion mixture. Cover with foil and cook at 325 for 4 hours.

Braised Brisket with Red Wine & Prunes
After the brisket has cooked, set it aside to cool, then blend the cooked vegetables, brunes, and cooking liquid together to make your sauce.

Braised Brisket with Red Wine & Prunes
Slice your brisket, smother it in sauce, and eat it up.

Braised Brisket with Red Wine & Prunes
Prep time: 
Cook time: 
Total time: 
Serves: 10-12 servings
Tender braised brisket with red wine, prunes, and sweet onions.
  • 5-6 pounds brisket
  • kosher salt and pepper
  • 2 tablespoons canola or vegetable oil
  • 3-4 large carrots, cut into ½-inch pieces
  • 3 stalks celery, cut into ¼-inch pieces
  • leaves of 2 sprigs of rosemary, leaves only, finely minced
  • 2 dried bay leaves
  • 25 pitted prunes
  • 2 large onions, thinly sliced
  • 2 heads of garlic, cloves removed and peeled
  • 2 cups dry red wine
  • ¼ cup plus 2 teaspoons red wine vinegar
  • 1 14.5 ounce can crushed tomatoes
  • ⅓ cup packed dark brown sugar
  • 2 cups beef or chicken stock
  1. Preheat the oven to 325 degrees F. Season the brisket on both sides well with salt and pepper, at least a tablespoon of salt per side and 2 teaspoons of black pepper per side (more or less depending on personal taste). Heat the oil in a large skillet (or the bottom of your roasting pan, like I did, because my 6-pound brisket would not fit in any of my pans) and brown well on both sides, about 6-7 minutes per side. Transfer the brisket to the rack of the roasting pan and surround with the carrots, celery, rosemary, bay leaves, and prunes.
  2. Add the onions to the same skillet (or a separate one with some oil, like I had to do, because, as I said, I bought a giant freakin' brisket) and saute over medium-high heat until well browned, about 8 minutes. Add in the whole, peeled garlic cloves, red wine, and ¼ cup of the red wine vinegar and stir to combine. Reduce the mixture until the pan is almost dry, about 10-15 minutes, stirring often, then add in the tomatoes, brown sugar, and stock. Stir to combine.
  3. Pour the onion mixture over the brisket in the roasting pan, and cover entirely with foil. Place in the oven and roast for 4 hours, or until tender (I found that 4 hours was perfect for my 6-pound brisket).
  4. Remove the brisket from the oven and uncover. Allow it to cool for 15 minutes, then transfer it to a cutting board and cover to keep warm. Discard the bay leaves, and use a slotted spoon to remove the prunes and set them aside. Strain the cooking liquid into a large bowl, and reserve 1 cup of the cooked vegetables, discarding the rest. Allow the fat to rise to the top of the bowl of cooking liquid, then skim it off with a spoon and add in the reserved 1 cup of vegetables and half of the prunes (you can cut up the prunes and add them to the sauce later, but I just used half of the prunes and discarded the rest). Place in a food processor, a blender, or use an immersion blender to puree the sauce. Add in the remaining 2 teaspoons of red wine vinegar, taste, and adjust seasonings as needed.
  5. Slice the brisket very thinly, against the grain, and serve with the sauce.


23 Responses

  1. Lindsey says:

    oh woah there, that brisket looks too good to be true! hope you feel better asap – drink like 3 packets of emergen-c and try and get some much needed rest!

  2. Oh man, I’ve been anxious to make some slow cooked meat lately but haven’t had enough time what with weddings, hangovers, work and travel. But Fall is for slow cooking and slowing down so soon I’ll be at the stove. Thanks for the jaw dropping inspiration. Get well soon, too.

  3. Anthony says:

    Sorry about the sinus cold — I hate those things with a “just shoot me now” kind of hate.

    I’ve heard of prunes with pork, but never beef. This brisket looks delicious.

  4. I LOVE Cards Against Humanity!

  5. I’ve never made brisket, but that definitely looks like a winner. Hope you feel better very soon!

  6. Sylvie says:

    Take some ginger to rid your cold/infection. Hope you feel better soon and the brisket looks yum.

  7. Feel better! And also, how wrong would it be to serve this amazingness for Thanksgiving instead of a turkey? :)

  8. Renate says:

    I am totally distracted by how one of your friends seems to point a finger in all the group photos (except one).

  9. Lynna says:

    Omgosh…the pictures are making me hungry even though I just ate!

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  11. Audrey says:

    I was probably picnicking in the background somewhere nearby at that same time in Prospect Park. It was glorious this weekend weather-wise. This brisket looks amazing. I may have to order one from our CSA asap! I will have to seek out Mile End Deli. I’ll add that to the bucket list, along with Walter Foods. Never heard of either of them.

  12. Laura says:

    That is a work of art.

    I loooove braised beef, especially this time of year. I made one myself last night, also with red wine, but with thyme and mushrooms. I’m pinning this one. No such thing as too many.

    Hope you feel better!

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  16. Ike says:

    I have this cookbook and was hoping to try this recipe this weekend. In the cookbook they don’t mention placing the brisket on a roasting rack as you did above. Was the brisket as moist as you’d hoped? Do you recommend using the rack? I guess I just envisioned the brisket sitting in the liquid to braise.

    Any answers would be appreciated. Thanks!

    • Sydney says:

      HI Ike – I actually used a roasting rack because they said to in the book…unless I am going crazy? Which is completely possible. Either way, I didn’t find it dry at all. I like to use a roasting rack for stuff like this because if you’re going to let it sit in all of that water/juice/etc. you might as well put it in the crock pot! Having it braise just above the liquid allows for some nice caramelization.

  17. aliktamar says:

    I made this a little over a week ago and people are still talking about. THANK YOU! Absolutely love your blog and recipes!!!

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  19. Jodi Hebeisen says:

    Made this for Roshashana — Amazing!!!!!!!! EVERYONE loved it and I was even able to send leftovers home and it was even better! It’s my new go-to holiday recipe! Thanks so much!

  20. Joanne Werner says:

    This recipe is amazing! Reminds me of the brisket my mother-in-law used to make but dare I say, this one turned out so much better! I did a trial run last weekend and it turned out so tender. Placing the brisket on the roasting rack worked out very well. I am now confident to serve it for Easter dinner.
    The Shiksa

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