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Flank Steak with Bloody Mary Tomato Salad

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Photo by Ditte Isager.
  • Active Time

    35 minutes

  • Total Time

    1 hour 40 minutes

Our favorite Bloody Mary fixings make a juicy accompaniment for grilled flank steak. The salad tastes better if prepared a few hours ahead.

Ingredients

Makes 8 to 10 servings

Steak:

2 1 1/2 pounds flank steaks
Kosher salt
2 teaspoons (packed) light brown sugar
1 teaspoon paprika
1/4 teaspoon cayenne pepper
1/4 teaspoon freshly ground black pepper
Vegetable oil (for brushing)

Salad:

1 cup finely chopped red onion
3 tablespoons Sherry vinegar, divided
2 pound cherry or grape tomatoes, halved
1 cup chopped celery hearts (inner stalks and leaves; from 1 bunch)
1/2 cup chopped brined green olives plus 2 tablespoons olive brine
2 tablespoons prepared horseradish
1 tablespoon Worcestershire sauce
1 teaspoon hot pepper sauce
1/2 teaspoon celery seeds
1/4 cup extra-virgin olive oil
Kosher salt and freshly ground black pepper
  1. For steak:

    Step 1

    Place steaks on a large rimmed baking sheet; season with salt. Mix sugar and next 3 ingredients in a small bowl; rub all over steaks. Cover; refrigerate 1-3 hours.

    Step 2

    Let steaks stand at room temperature for 1 hour. Build a medium-hot fire in a charcoal grill, or heat a gas grill to high. Brush grates with oil. Grill to desired doneness, about 5-7 minutes per side for medium-rare. Let rest for 10 minutes. DO AHEAD:Can be made 1 day ahead. Let cool; cover and chill. Bring to room temperature before slicing.

  2. For salad:

    Step 3

    Mix onion and 1 tablespoon vinegar in a large bowl. Let macerate 10 minutes, tossing often. Add tomatoes, celery, and olives.

    Step 4

    Whisk remaining 2 tablespoon vinegar, olive brine, horseradish, and next 3 ingredients in a medium bowl. Slowly whisk in oil. Add to bowl with tomato mixture; toss to coat. Season with salt and pepper. DO AHEAD:Can be made 4 hours ahead. Cover; chill.

    Step 5

    Cut steak crosswise into 1/4"-thick slices. Serve salad with steak.

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Reviews (35)

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  • Loved it! Easy to make and much can be made ahead of time. Great for entertaining. The star of this is the bloody mary salad - very good. The rub was good.

    • Anonymous

    • Chicago

    • 6/15/2020

  • Only made the steak. It was good.

    • Anonymous

    • Seattle

    • 2/13/2017

  • OUTSTANDING! The steak rub had a nice flavor but the real treat is the bloody mary tomato salad. That was fantastic and can go with just about any kind of meat. Everyone was crazy about the tomato salad.

    • penntex

    • Lawrence, KS

    • 9/2/2015

  • The salad was an interesting twist with the dressing making it unusual - will keep it in the repertoire. The kitchen smelled like a Bloody Mary with the Worcestershire and horseradish. My husband normally doesn't eat celery, but he ate it in the salad. Used regular tomatoes and it got too juicy after sitting for awhile. Would be much better with the cherry tomatoes. Used a different flank steak recipe.

    • bugthecat

    • Ottawa

    • 7/27/2015

  • My husband and I have now served this at two dinner parties, to excellent reviews by our guests. The flank steak is terrific. As for the bloody-mary salad, naturally the quality of the tomatoes is important. But here's the thing. The first time I made it the tomatoes I bought were a little too soft--some of them were in fact over-ripe (I tossed them) and all of them very juicy. I was worried that the salad would be a disappointment. It was great. The second time the tomatoes I bought had much firmer skins, and I thought the salad would be even better. Wrong. It didn't macerate properly until a day or two later. Go figure! --One more observation: I was worried about chilling the salad in the refrigerator because (as Epicurious cooks know) refrigeration ruins tomatoes. However that proved not to be the case with this salad. Overall, a really great pairing that we will definitely make again.

    • yiddishekoppe

    • Dallas, TX

    • 8/16/2014

  • We had our first annual New Year's Day brunch yesterday :) and while I didn't make the flank steak, I did make the Bloody Mary Tomato Salad. Everyone (who likes both tomatoes and olives) LOVED it! Everyone commented on how different and delicious it was. It was simple to make and I made it 4 hours ahead, as it said it would be okay - and it was. I'll make it again.

    • TerryKes

    • Illinois

    • 1/2/2014

  • 我使这道菜几次,冰原r fails to please. Perfect way to "wake up" a flank steak. Served with boiled baby red skin potatoes and French green beans with butter and Dijon mustard. Just right.

    • tgbixby

    • Farmington Hills, MI

    • 7/22/2013

  • Easy, delicious & really quite pretty. Perfect for summer! My flank steak was a little thinner and I didn't pay quite enough attention...first side got a little toasty. If you're using a thinner cut...be SURE to watch the clock! Otherwise...yum! I will so be making this again!

    • Anonymous

    • San Diego, CA

    • 6/17/2013

  • I love the play on bloody marys in this salad, and it really is beautiful if you use a mixture of red and yellow tomatoes. I've made this recipe twice so far, but with flatiron steak. Fabulous for summer.

    • lschmidt

    • Portland, OR

    • 6/4/2013

  • I have made this recipe twice, without modification, and served it with roasted potatoes. It is a pretty presentation, tastes good and keeps well for leftovers the next day.

    • Anonymous

    • Farmington Hills, MI

    • 10/12/2012

  • The steak was okay. The salad was a total flavor-bomb!

    • Anonymous

    • Harleysville, Pa

    • 9/2/2012

  • great idea! i added chopped pickles to the salad, since i love a good dill note in a bloody mary. i added some wetness to the marinade with a bit of worcestershire and hot sauce. i served this with honey glazed cornbread.

    • walrusgumbo

    • 7/18/2012

  • Excellent! The rub is really nice; made with chicken instead of beef.

    • Anonymous

    • Monterey Hills, CA

    • 7/15/2012

  • First time cooking flank steak and as other reviewers pointed out (a) dry rub made too little and (b) a wet marinade would be better to keep the meat tender. The tomato salad is a keeper and went really well with the meat. Its flavor is bold and really made the celery shine- usually celery is hum hum for me but it popped in this recipe. A few changes to the salad, I used a mixed black/green mediterranean olive blend which cut the brinyness down and added a 1/4 cup tomato juice to the dressing. Made everything the morning of and then threw the meat on the grill for no more than 10mins total. Served with Corn and onion grits and lettuce salad. Delish, easy and I would definitely would make this again.

    • chickelala

    • Iowa

    • 6/3/2012

  • Leftover salad is terrific w/ the addition of a can of drained black beans & avocado. I used one 1.5# flank steak but still doubled the rub. Leftovers make outrageously delicious sandwiches (use ciabatta) that are exceeeeeedingly picnic worthy!

    • manhattantart

    • Manhattan Beach, CA

    • 5/4/2012

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