One of the many reasons steak is well loved I think, is it's versatility. It goes with so many wonderful flavor combinations. This time of year, when cherries are abundant at the markets, I make Red Onion Jam with them and pair them with steak, a salad, and a little blue cheese. Everything can be made ahead and just assembled for dinner. —TheWimpyVegetarian
Red Onion Jam
2 medium red onions, halved and thinly sliced lengthwise
2 tablespoons unsalted butter
1/8 cup (1 ounce) granulated sugar
1/8 cup (1 ounce) brown sugar
1/4 teaspoon kosher salt
1/8 teaspoon ground black pepper
1/3 cup (about 12) fresh, sweet, ripe cherries, pitted
1/3 cup red wine (Pinot Noir and Zinfandel work well)
1 tablespoons sherry vinegar
3/4 teaspoon fresh thyme leaves
slices of Na'an bread
2 cups arugula, washed and dried - enough for 2 sandwiches
Melt the butter in a saute pan over medium heat. Add the red onion and toss to coat. Once the onion begins to soften and melt into the saute pan, add the sugars, salt and pepper. Toss well again and reduce the heat to medium-low. Cook for approximately 30 minutes, turning the onions occasionally. By then the onions should begin to caramelize. If not, cook longer. Tip: the more the onions are tossed around in the saute pan, the slower they will caramelize. I toss mine around about every 5 minutes.
When they begin to caramelize, add the wine, sherry wine vinegar and cherries. Continue to cook on medium-low heat another 15 minutes until the cherries are very soft, the liquid is absorbed / cooked off, and the onions are caramelized.
Remove from the heat and toss in the fresh thyme leaves. Let cool to room temperature.
Salt both sides of the flank steak and bring to room temperature, about 30 - 45 minutes. Using a paper towel, dab any moisture off the steak surfaces.
Combine the brown sugar, salt, thyme, and ground peppers in a small bowl. Rub on the dry steak surfaces. Heat up the grill. Grill the steak over direct heat about 4 minutes per side for medium rare.
Toast the Na'an bread on the grill. Toss the arugula in the olive oil and balsamic vinegar. Set aside.
Assemble your sandwiches: Spread a good thickness of the red onion jam on the toasted bread. Place the arugula on top. Sprinkle a some blue cheese on a cutting board and place the steak on top of it. Slice the meat against the grain. Sprinkle more blue cheese on top and layer the slices over the arugula.
Pour the rest of the Pinot Noir or Zin in a couple wine glasses and relax.