There’s something undeniably special about cookies and our time-honored tradition of sharing them, particularly this time of year. Deliciously gift-able and grab-able, they’re the perfect holiday dessert.
That’s part of what makes the Tribune’s Holiday Cookie Contest such a treat to come back to year after year. It’s an enduring tradition (35 years strong!) because it gives us the chance to share something we put so much love into with a community reaching even wider than our own friends and family.
Flipping through pages of the cookbook featuring winners from the first decades of this contest, that community comes to life, as each baker’s story and their resulting recipes are so filled with love — love shared between family members who pass on cherished blueprints to re-creating the taste of home, love between friends and a shared passion for translating that love into nourishment.
This year’s contest, sponsored by Jewel-Osco, featured a strong cohort of contestants, with 35 entrants vying for our first-place prize of $250 and eternal cookie glory. For one week in early November, readers could vote for their favorites, and 1,671 votes were cast, leaving us with 12 finalists whose recipes were then baked and judged by Tribune staffers.
While we did leave in place the option to “save” a 13th contestant that didn’t quite make the voting cutoff, it went unused this year. However, keep your eyes peeled in 2022 for our Joe Gray Save, named in honor of our previous Dining editor.
The finalists put up an excellent show. I found myself most drawn to the simple cookies that were exceedingly well-executed, like Donna Rajchert’s ruszki, a buttery, nutty cookie with the perfect texture and ideal two-bite size. A surprise favorite among our judges was Ann Henry’s “So Puckin’ Good” Hockey Pucks, absurdly simple (just three ingredients!) but undeniably craveable.
But the beauty of having 10 judges ranking the cookies for their appearance, flavor and originality is that no single judge could decide the winners. As we tallied the scores, I was surprised to see which flavors and textures resonated most with our taste testers.
Many of the cookies that didn’t win were still quite delicious — I know I’ll be making Mary Kim’s mulled wine cheesecake Snuggle Bars again very soon (though I’ll leave off the optional glaze to better enjoy the swirled pattern of the purple-hued filling).
You can find all 12 finalist recipes at chicagotribune.com/cookies, and the winning three are below, along with the stories of how they came to be.
What I love about the winners this year is how different each recipe is: a butterscotch-studded oatmeal cookie that seems to capture the essence of home; an attractive Italian petit four-esque delicacy steeped in tradition; and a showstopping shortbread cookie with a surprise ingredient that adds a crisp freshness to buoy the dark chocolate and crushed pistachios appealingly topping each bite. — Ariel Cheung
Want an inside look at the Holiday Cookie Contest? Join us for a live chat with Tribune critics Louisa Chu and Nick Kindelsperger and our first-place winner on what it takes to make the perfect holiday cookie at noon Thursday on the @ChiTribFood Instagram.
THIRD PLACE
Sean Doe-Simkins: PB Oatmeal Scotchies
As if taking a page from “The Great British Baking Show,” Sean Doe-Simkins deliberately chose to submit a “technically challenging” recipe for this year’s cookie contest. Not because he was bored of submitting “easy ones” (he’s never participated in a baking contest before), but because he thinks this is the time of year to do it.
“I wanted to make a recipe that was involved — it’s the time of year when you pull out your harder recipes and when you kind of want to show off a little bit,” he said.
His recipe for PB Oatmeal Scotchies is intentionally flashy. There’s a homemade granola component and an option to caramelize white chocolate.
“I love to bake; I always bring baked goods and cookies to family gatherings, so my father-in-law sent me a link to the contest and said ‘I think you should do this,'” Doe-Simkins said.
He was a little wary at first, never having created his own recipe, he said.
“So I thought back about what it is that I love about cookies and the first cookie I ever made,” he said. “Oatmeal cookies from the recipe on the back of the Quaker Oats container.”
He set out to make the best version of that nostalgic oatmeal cookie by elevating each step of the process.
“I think the secret to roasting your own white chocolate is you’ve got to stir it pretty frequently. I’ve made batches myself where the chocolate scorches and gets all crumbly. It also needs to be white chocolate that has a high cocoa butter content like Valrhona,” he said.
Doe-Simkins lives in Oak Park, writing software and working on front-end web development by day. In true millennial fashion, he doesn’t have cable but has spent many pandemic hours watching baking competitions and cooking shows, much like he did when he was younger.
“When I was a kid, my parents didn’t really let me watch a lot of TV, but I was allowed to watch all the PBS I ever wanted,” he said. “So I watched a lot of old episodes of ‘The French Chef’ with Julia Child and old episodes of ‘Lidia’s Kitchen.'” He’s been curious about kitchen techniques since.
While this contest was a first for Doe-Simkins, he said his third-place finish was even more gratifying because developing his own recipe was also a first.
“My sister was asking me about this, she was like, ‘Well, if it goes well, are you going to make a cookbook, what’s your next move?'” he said with a laugh. “So yeah, clearly after winning one newspaper contest, the next step is bestselling cookbook.” — Zareen Syed
SECOND PLACE
Annamaria Arena: Venetian Cookies
There’s a certain sense of kismet at play, for a teen born on Christmas Day to place in a holiday cookie contest.
“I really like baking, and I want to own a bakery when I’m older,” said Annamaria Arena, 15. “We make cookies every year, and I thought it would be fun.”
Her Venetian Cookies, an Italian-American concoction also known as marzipan cookies, rainbow cake or seven-layer cookies, were made with a recipe handed down from Annamaria’s grandmother (and partial namesake), Maria Arena, and happen to be striped with the red, white and green of both Christmas and the Italian flag.
Annamaria has been baking on her own for about four years, but has always loved helping her parents in the kitchen, she said. These days, she bakes cakes for her parents’ birthdays (“I did a couple for my dad that totally failed,” she concedes), and joined the baking club at Jones College Prep, which hosts virtual bakes over Zoom for students to test out the same recipe together.
“She has just always been immersed in it, and she has far surpassed anything I can produce,” said her father, Ross Arena. “She’s always been around a lot of people who cook a lot, and it’s nice to see that get carried on.”
As a first-generation Italian American, Ross Arena does his fair share of cooking and baking, as well, as does Annamaria’s mother, he said.
“The kitchen is a central gathering place in our life,” he said. “We still have Italian Sundays, where I’m in the kitchen all day cooking.”
His mother, who lives in Ohio, passed her Venetian Cookie recipe down to Annamaria, who has “perfected it over the years,” her father said.
“She’s very creative,” Ross Arena said of his daughter. If she does end up becoming a professional baker, “I have no doubt she will be successful at that,” he said. “I’m just proud of her every day. She’s a wonderful human being.”
As for Annamaria, she plans to keep baking — and to “up the ante” for a cake for her brother, who shared the Holiday Cookie Contest voting link with his friends to help her win. With the holidays coming up, she’ll be baking more cookies, including peanut butter Buckeyes, and the Venetian Cookies that have been handed down for generations.
“I think my Nonna got the recipe from her mom,” she said. “It’s a family thing.” — A.C.
FIRST PLACE
Kathleen Robinson: Mint Pistachio Choco-Chunk Shortbread Cookies
“The mint and the pistachio and the chocolate, those are the dynamic trio in a flavor combination for me,” said Kathleen Robinson. “And that chocolate drizzle on top, with the pistachio crumb, and the outside rim of demerara sugar, they all give you a look into the textures and flavors you’re going to get when you bite into the cookie for the first time.”
If it sounds like Robinson, 26, has thought a lot about how to describe her award-winning cookie in loving detail, you might think it’s because she works in hospitality and restaurant public relations as a digital marketing manager. But her love of baking goes back much further. She currently lives in the Bucktown neighborhood of Chicago, but grew up making cookies with her mother in St. Louis.
“We had these very extravagant holiday cookie decorating days that sort of started with my neighbors when I was a little kid, and then evolved into me inviting my high school friends over to my house,” Robinson said. “Everyone always laughed at me, because I pulled out tweezers to put tiny little sprinkles on a cookie in just the right place.”
They still get together when they’re home for the holidays to decorate Christmas cookies. This recipe, however, she developed just for the contest.
“Last year, I took this virtual baking course with Christina Tosi,” Robinson said. (Tosi is the award-winning pastry chef who founded Milk Bar in New York City). “It was a monthlong intensive course with one of my culinary idols. She taught us all about finding flavor stories, developing base recipes, incorporating fun mix-ins and different elements.”
Robinson started with a base recipe of shortbread dough for this holiday cookie.
“I love the buttery flavor and texture of shortbread cookies,” she said. “And then I decided on the mix-ins I wanted: pistachios and dark chocolate.”
The tricky part came when she wanted to use fresh mint, not the mint extract you usually find in holiday cookies. She experimented with varying degrees of success.
“I tried infusing the fresh mint into the butter first, and then pouring melted butter into the cookie dough, which didn’t give me the texture I wanted,” she said.
Then she tried pulsing the mint leaves in a food processor with granulated sugar.
“That gave the dough such a good subtle flavor of mint throughout,” she said. “I went through a few more iterations, so I’m excited that it kind of works and everybody liked it.”
They did indeed, from her recipe testing friends and family, to cookie contest judges. Robinson, though, seems to love the process of baking the best.
“Baking has been a source of comfort for a lot of people through all of this,” she said. “And that’s really what I have enjoyed about baking during this time as well.
“Giving myself projects like this has really been such a source of joy throughout the pandemic,” she added. “So I’m really glad that the Chicago Tribune has continued to do this, and I’m just really excited that I got to participate.” — Louisa Chu
RECIPES
Third place: PB Oatmeal Scotchies
Prep time: 75 minutes, plus overnight cooling of dough
Bake time: 30 minutes
Yield: 32 to 44 cookies
Ingredients
Butterscotch chunks:
8 ounces quality white chocolate (look for at least 30% cocoa butter)
?-1/4 teaspoon sea salt, to taste
Maple granola:
2 cups old-fashioned rolled oats (not quick)
1/4 cup dark brown sugar
1/2 teaspoon ground nutmeg
1/2 teaspoon sea salt
4 tablespoons maple syrup
2 tablespoons vegetable oil, such as canola
1/2 tablespoon vanilla extract
Cookies:
Butterscotch chunks, recipe above
Maple granola, recipe above
1 3/4 cups all-purpose flour
1 teaspoon baking powder
1 teaspoon baking soda
1/2 teaspoon sea salt
? cup creamy peanut butter
2 large eggs
2 teaspoons vanilla extract
? cups dark brown sugar
2 sticks unsalted butter
Directions:
Caramelize the white chocolate:
1. Preheat the oven to 250 F. If chocolate isn’t already in discs or chunks, coarsely chop it. Place the chocolate into a small glass baking dish or rimmed baking sheet.
2. Roast the chocolate until a rich, golden brown, about 25 to 30 minutes. Stir the melting chocolate with a silicone spatula or spoon every 5 to 10 minutes. Don’t panic if chocolate gets crumbly; with a little pressure you can smooth it out. Toward the end of roasting time, it is possible that the chocolate will break, meaning it will be irrevocably crumbly. This is also fine! These crumbles can be added to the recipe just as easily.
3. Remove chocolate from the oven and cool. This will take quite some time, up to overnight. Avoid the urge to put it in the fridge and be sure not to cover it, just let it do its thing. If you happen to ignore that last instruction, it’s probably no big deal, you just may get some moisture that affects the texture.
4. Once cool, chop, snap or crumble the caramelized white chocolate. Store in an airtight container until ready to bake the cookies.
Make the granola:
5. Preheat the oven to 225 F. Line a baking sheet with parchment.
6. In a large bowl, toss the dry ingredients together. Add maple syrup, oil, and vanilla extract and stir until coated. Spread evenly onto the sheet pan.
7. Bake for 20 minutes, rotating the pan halfway around at 10 minutes. Let granola cool in the pan on a wire rack until room temperature. Granola will crisp as it cools. If making the granola awhile before you plan to bake the cookies, store it in an airtight container until ready.
Bake the cookies:
8. Whisk together dry ingredients in a small bowl: flour, baking powder and soda, and salt. Set aside.
9. Cream together sugar and butter. In the bowl of a stand mixer (a hand mixer is fine, of course, just takes a bit more time and effort), beat butter at medium speed until it’s pale, puffy, and makes you want to take a swipe with your finger.
10. Add sugar and peanut butter and continue beating until mixture is even fluffier. Creaming the butter and sugars is probably the step most frequently rushed through. But don’t! This step is important because it’s when you dissolve your sugars into the small amount of water that is suspended in your butter. This is your first step in the foundation of building the texture (read: chew) of your cookie. So let that mixer run. I like to use this time to finish measuring out the rest of my ingredients.
11. Lower speed; add eggs one at a time with mixer still running. Scrape down the sides and add vanilla. Scrape again and beat for another 30 seconds. Remove bowl from mixer.
12. Add dry ingredients and stir by hand until just combined. Streaks are OK because you still have some stirring coming up.
13. Add granola and caramelized white chocolate bits. Give several more hearty stirs, being particularly sure to dig down to the bottom of the bowl to ensure everything is thoroughly mixed.
14. Rest the dough for 30 minutes or up to overnight. Resting your dough lets the flour fully hydrate, and this helps yield that perfect crispy edge and chewy, gooey middle texture. It also allows for more even baking and caramelization of the sugars, giving us a tastier flavor.
15. Preheat the oven to 375 F. Set oven racks to top and bottom third. Line your baking sheets with sheets of parchment.
16. Scoop the dough into 2-tablespoon portions and place on the sheet with plenty of room for spread (6 to 8 portions per sheet is a good target).
17. Bake for 8 to 12 minutes until just set, rotating halfway through. Cool cookies on sheets for five minutes and then transfer to wire racks. Cookies are delightful when they’re still a little warm. Enjoy with a small glass of very cold milk.
Tip: To test if the cookie is done, bake it just until you can tap the edge of the cookie and it’s set. At this point, it’s done. If the centers look particularly underdone, leave the cookies on the sheets until they come to room temperature. There you go, the key to never overbaking your cookies again!
Baker’s note: I’ll concede, caramelizing your own white chocolate is a ludicrous labor of love. Instead, you can buy this ingredient pre-caramelized or just go with a regular old bag of butterscotch chips, which is still delightful.
Nutritional information per cookie (based on 32-cookie yield): 202 calories, 12.3 g fat, 5.9 g saturated fat, 28 mg cholesterol, 20.2 g carbohydrates, 10.7 g sugar, 3.6 g protein, 191 mg sodium, 1 g fiber
Second place: Venetian cookies
Prep time: 75 minutes, plus cooling time for cookie sheets
Bake time: 8 to 10 minutes
Assembly time: 15 minutes, plus 2 or more hours for chilling
Yield: 48 cookies
Ingredients:
6 eggs (separated)
1 1/2 cups granulated sugar
1/4 teaspoons cream of tartar
4 sticks unsalted butter
1 teaspoon almond extract
12 ounces almond paste
3 cups flour
1/4 teaspoon salt
2 cups apricot preserves
2 cups chocolate chips
4 to 5 drops each of red and green food coloring
Directions:
1. Preheat oven to 350 F and grease three cookie sheets
2. With an electric mixer with wire whisk attachment, beat the egg whites, 1/2 cup sugar, and cream of tartar for 2 to 3 minutes or until stiff. Set aside for later.
3. In a different bowl, use the mixer’s paddle attachment to cream the butter and the last 1 cup of sugar. Once mixed, add egg yolks and almond extract. Break up the almond paste into bits and add it to the butter mixture little by little. Finally, add the flour and salt and mix until everything is blended.
4. Fold the egg white mixture into the butter mixture.
5. Separate the dough into three parts. Dye one green, one red, and leave the other one natural.
6. Spread each dough on to the cookie sheets to create thin layers.
7. Bake for 15 minutes or until the edges began to brown.
8. Remove cookies out of the oven and let them cool.
9. Once cooled, flip out of the cookie sheets and get ready to stack the layers. Start with the green layer and spread one cup of apricot preserves on it before stacking the natural colored layer on top. Spread the other cup of apricot preserves on the natural layer and stack on the red one. Cover with plastic wrap and weigh the stack of cookie layers down with a cutting board or something semiheavy. Refrigerate for a couple of hours.
10. Melt the chocolate chips and spread the melted chocolate over the red layer. Let the chocolate set.
11. Use a knife to trim the dry edges and cut the rest into 1-inch squares.
Nutritional information per cookie: 230 calories, 12.1 g fat, 7.2 g saturated fat, 42 mg cholesterol, 28.4 g carbohydrates, 18.3 g sugar, 2.8 g protein, 31 mg sodium, 0.8 g fiber
First place: Mint Pistachio Choco-Chunk Shortbread Cookies
Prep time: 40 minutes, plus 6 or more hours chill time
Bake time: 12 to 16 minutes
Yield: 24 cookies
Ingredients:
Cookie dough:
1/2 cup granulated sugar
? cup loosely packed fresh mint leaves (1 3/4-ounce clam shell package)
2 sticks + 2 tablespoons unsalted butter, softened to room temperature
1/4 cup packed light brown sugar
1 teaspoon pure vanilla extract
2 1/4 cups all-purpose flour
4 ounces dark chocolate, coarsely chopped
? cup coarsely chopped pistachios (salted and roasted)
1 egg, for brushing
Demerara or coarse sugar, for rolling
Decoration:
4 ounces dark chocolate, melted
Handful of pistachio crumbs
Flaky sea salt (like Maldon)
Directions:
1. Pulse granulated sugar and fresh mint leaves in a food processor until mint is finely chopped.
2. In a large bowl using a hand-held mixer or stand mixer fitted with a paddle attachment, beat butter, granulated sugar-mint mixture, brown sugar, and vanilla on high speed until completely smooth and fluffy, about 5 minutes (if using a stand mixer, pause halfway through to scrape down the sides of the bowl).
3. Add flour and mix on low speed just until dough begins to form (no longer than 30 seconds). Add chopped chocolate and chopped pistachios and mix on low speed until just combined (about 20 more seconds).
4. Divide the dough in half and place each half on a large piece of plastic wrap. Shape each half into an 8-inch log, about 2 inches in diameter (doesn’t have to be exact), and tightly wrap the logs in the plastic wrap.
5. Chill in the fridge until firm, for at least two hours (or up to 4 to 5 days).
6. Preheat oven to 350 F. Line two baking sheets with parchment paper and set aside.
7. Using a pastry brush and the beaten egg, thinly coat the outside of each dough log. Roll each log in Demerara or coarse sugar, using hands to help coat any empty spots.
8. Using a nice, sharp knife, carefully slice each log into about 1/2-inch rounds (err on the thicker side when slicing to avoid breaking or crumbling the dough).
9. Place on the baking sheet about 2 inches apart and bake for 12 to 16 minutes, until brown around the edges. Once slightly cooled, transfer to a wire cooling rack and allow to cool completely.
10. Once your cookies are cooled, melt the dark chocolate and drizzle over the cookies using a fork or by placing into a Ziploc bag, cutting a tiny hole at the corner, and piping. Sprinkle each cookie with pistachio crumbs and flaky sea salt.
Nutritional information per cookie: 205 calories, 13.4 g fat, 7.9 g saturated fat, 30 mg cholesterol, 21.4 g carbohydrates, 10.6 g sugar, 2.8 g protein, 77 mg sodium, 1.8 g fiber
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