Tomato Stack Salad with Black Olive Tapenade & Sweet Basil Vinaigrette
The saltiness of the Tapenade combines with the sweetness of the Sweet Basil Dressing to create a sublime Caprese Salad on steroids. Use heirloom tomatoes if you can find them.
I'll give credit to Bobby Flay for this recipe from his mid-2000s show Boy Meets Grill. This was a time when venerable chefs and restaurateurs actually taught you how to prepare food on a cable channel called the Food Network. Today, the channel has devolved to airing mostly inane, food-themed, game-shows and restaurant critic exposés that never seem to review a mediocre meal. My Number One Fan made this dish several times and then we forgot about it, leaving the 2007 notated, dog-eared printout of the recipe in one of our multiple three-ring binders full of categorized recipes. But then, we resurrected it and remembered how good it was.
The recipe has undergone very little modification from its original version. However, it yields enough Tapenade and Sweet Basil Dressing for three pounds of tomatoes. That's about three large beefsteak tomatoes or six medium tomatoes on the vine. My Number One Fan makes the full recipe, though, and then we prepare the individual portions of Tomato Stacks with our meals off and on over several weeks. The Tapenade and Sweet Basil Dressing will keep refrigerated up to a month.
Kitchen Tapestry has a Green Olive Tapenade recipe posted nearly a decade ago, but most Tapenades are made like the one in this recipe, with black and/or Kalamata olives. Tapenade is a Mediterranean olive condiment, or more specifically, a Provençal delicacy from southern France, wherein olives are finely minced with capers and anchovies and then mixed with a little olive oil and seasoned with some lemon juice and herbs. Beyond the first three ingredients, there are wide variations from region to region and chef to chef, including Bobby's addition of garlic and pine nuts. He actually leaves out the capers. I recommend including them, but added at the last un-minced.
Use heirloom tomatoes if you can find them, but red, ripe beefsteak tomatoes or tomatoes on the vine work well too. Obviously, the more garden-fresh your tomatoes, the better this recipe will taste.
Tomato Stack Salad with Black Olive Tapenade & Sweet Basil Vinaigrette

Ingredients
- 3 or 4 half-inch thick slices of tomatoes per serving
- 2 or 3 thin slices fresh mozzarella cheese per serving (like, BelGioioso)
- 2 or 3 fresh basil leaves per serving, chiffonade
- 3 cups Kalamata olives, pitted (like Mezzetta)
- 3 tsp garlic, minced
- 5 anchovy fillets or 1- 1/2 tbsp anchovy paste (like, Reese)
- 2 heaping tbsp pine nuts
- 1/2 cup extra virgin olive oil
- 1/4 cup non-peril capers, drained (like, Goya or Cross & Blackwell or Goya)
- 1/4 tsp freshly ground black pepper
- 1/4 cup red wine vinegar
- 1 tbsp Dijon mustard (like, Grey Poupon)
- 2 tbsp honey
- 3/4 cup extra virgin olive oil
- 12 fresh basil leaves, chiffonade
- 7-8 grinds freshly cracked black pepper
Instructions
- Combine the olives, garlic, anchovies and pine nuts in a food processor and pulse until a smooth paste is formed.
- With the motor running, slowly add the olive oil until emulsified.
- Season with black pepper. Because of the saltiness of the olives and anchovies, you will not need additional salt.
- Add the capers to the mixture whole and then gently stir into the mixture to combine.
- In a small mixing bowl, whisk together the vinegar, Dijon mustard and honey.
- Whisk in the olive oil until emulsified.
- Season with freshly ground black pepper.
- Stir in the chiffonade of fresh basil.
- Place a tomato slice on a salad plate and spread on a teaspoon or so of the Tapenade.
- Place a slice of mozzarella on top, then add another tomato slice.
- Repeat to make the stack as high as you wish, however, anything more than 3 or 4 slices becomes less manageable.
- Finish with a drizzle of dressing over the whole stack and garnish with the basil chiffonade.