Caramelized Leeks with Roasted Tomatoes and Pomegranate

This dish was created for a Rosh Hashanah gathering. Leeks and pomegranates are both symbolic foods traditionally eaten for the Jewish New Year, and while tomatoes aren't an official symbolic food, they are (1) round, and can thus be used in lieu of more traditional apples to symbolize the roundness of the year, (2) linguistically tied to apples in Italian and (3) still abundant and delicious. The inspiration for this dish is a simpler leek-and-tomato mezze dish my father always makes for Rosh Hashanah; I've cooked the leeks longer, roasted the tomatoes instead of frying them, and added pomegranate seeds, pomegranate molasses and lemon zest.

The Symbolic Props

3 tablespoons olive oil
2 whole large tomatoes (I used Black Prince)
2 large leeks, rinsed and bottom part sliced thinly
Salt and pepper to taste
2 tablespoons pomegranate molasses
zest of 1/2 a lemon
seeds from 1/2 a pomegranate
minced parsley for the top

The Method

Preheat oven to 300. Coat the whole tomatoes in one tablespoon of the olive oil, place on a cookie sheet and roast in the oven for 1 and a half to 2 hours.

Meanwhile, heat the remaining two tablespoons of olive oil in a cast-iron skillet. Add leeks, salt and pepper. Saute leeks slowly over medium-high heat, stirring so they don't burn to the bottom, for 30-45 minutes, adding more olive oil if needed. They'll slowly start to wither and brown--I took mine off after 30 minutes because I had to get out of the house ASAP, but they could have gone for longer.

When leeks and tomatoes are done, roughly chop tomatoes and add to a serving bowl with the leeks. Stir in pomegranate molasses and lemon zest and taste for salt and pepper. Top with parsley and pomegranate seeds.