When one thinks about eating dessert, the words "pain and suffering" rarely come to mind. Oddly enough, however, a handful of popular Jewish sweet foods specifically commemorate unhappy events in Jewish history. The most famous example is hamantaschen--the tri-cornered pastry that represents the hat (or ear or pocket, depending on whom you ask) of Purim's notorious villain and oppressor, Haman. Likewise, the Passover seder plate includes a scoop of haroset--a tasty amalgam of sweet and sticky ingredients that, when combined, resemble the brick mortar used by the enslaved Israelites in Egypt. 
A third example of the "sad sweets" phenomenon comes from Italy. On Rosh Hashanah, Italian Jews serve sfratti--a stick-shaped cookie made from honey and walnuts. The name sfratti comes from the Italian word sfratto, which means "eviction." According to The Classic Cuisine of the Italian Jews by Edda Servi Machlin, "There was a time when the law that prevailed was the 'law of the stick.' When landlords could not collect from poor tenants, they would evict them with the persuasive aid of a stick. The same treatment was applied to the Jews when they were no longer wanted in a community."
The Jewish fascination with depressing desserts in general, can be interpreted either as an attempt to dust a little sugar over bad memories--or to immortalize the centuries of oppression and scorn as if to say, "Even in the good times, we must remember the bad." Consuming a dessert that represents a negative experience inherently implies that the Jewish people have not only survived through the era of hardships, but thrived enough to have a little dessert. In other words, sfratti--like hamantaschen or haroset--are a tasty embodiment of the celebratory phrase: "They tried to kill us, we survived, let's eat!"
Recipe adapted slightly from The World of Jewish Desserts by Gil Marks.
Makes 42 cookies.
This is not your average chocolate chip cookie recipe--sfratti take time, patience, and finesse. You can make the dough in advance, but once you start the filling, things can get labor-intensive. Have all your filling ingredients prepared and your baking sheets ready to go before you begin making the filling.
Dough
3 cups unbleached, all-purpose flour
1 cup sugar
pinch of salt
1/3 cup cold, unsalted butter (or 1/3 cup vegetable oil)
approximately 2/3 cup chilled, dry white wine
Filling
1 cup honey
2 cups chopped walnuts
2 teaspoons grated orange zest
3/4 teaspoon ground cinnamon
1/4 teaspoon ground ginger
dash of nutmeg
1/4 teaspoon freshly grated black pepper
Egg Wash
1 large egg beaten with 1 Tablespoon of water
Make dough first: Combine flour, sugar, and salt in a medium bowl. Cut in the butter until it resembles coarse crumbs. Add the wine a little at a time, mixing with a fork to moisten the dough. Continue adding wine until the dough just holds together. Divide dough in half and press into balls. Flatten balls into discs, then wrap and refrigerate for at least an hour.
Dough can be made up to 3 days ahead. When ready to use, allow dough to stand at room temperature until malleable but not soft.
Make the filling: In a medium saucepan over medium heat, bring the honey to a boil and cook for 5 minutes. If it starts to foam over, lower heat slightly. Add remaining ingredients and cook, stirring constantly for another 3-5 minutes, then remove from heat. (If the mixture begins turn dark, it is starting to burn--remove from the heat immediately and keep stirring!)
Let the mixture stand, stirring occasionally, until it is cool enough to handle. Pour mixture onto a floured surface, divide into 6 equal portions, and shape the portions into 14-inch-long sticks.
Preheat the oven to 350°F. Line a large baking sheet with parchment paper.
Prepare the cookies: On a piece of waxed paper or plastic wrap or on a lightly floured surface, roll each disc of dough into a 14-by-12-inch rectangle, then cut each rectangle lengthwise into three long rectangles. Place one of the strips of filling near a long side of each rectangle, then roll the dough around the filling.
You will have six long sticks of dough with filling in each. Cut these into 2-inch sticks. Place seam side down on the prepared baking sheet, leaving 1 inch between the cookies. Brush with the egg wash.
Bake cookies until golden, about 20 minutes. Transfer to a rack and let cool. You can store them in an airtight container at room temperature for up to 2 weeks.
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