CHICAGO — In 1995, Agnes Da Costa won fourth place in the Tribune’s 10th annual Holiday Cookie Contest with the sweetly named Friendship Cookies.
And while that might not be the most prestigious accolade in all of baking, I find myself flipping to her well-thumbed recipe in our “Holiday Cookies” cookbook again and again, making the simple drop cookie (the recipe only takes about 30 minutes from start to finish) for family, friends and, just as frequently, myself.
To me, this is what makes a perfect holiday cookie: An easy recipe for the busy holiday season yields a small gift of love and friendship to be shared with those we hold dear, with a little something special to make them stand out. This also happens to be what I love about the three winning recipes in this year’s Holiday Cookie Contest — now in its 36th year.
From a delicious shortcut using Rolo candies in decadently chocolatey cookies, to the sweet cinnamon lacing our third-place sugar cookie recipe, each of the winning cookies has a unique touch that left a lasting impression on our dozen judges from the Tribune newsroom. And yet, two of them can be made in under an hour.
This year’s contest featured an impressive range of recipes, from lijena pita, a Serbian apple pie-like cookie made for St. Nicholas Day, to galletas grageas, a Mexican cookie coated in a rainbow of nonpareil sprinkles. Delicately pink Candy Cane Crush cookies — which lost out on a third-place win by a fraction of a point — were a surprise favorite, with one judge in our “sugary slug fest” applauding the baker for “wisely subtle” mint flavor.
We had 35 entrants vying for the $250 first-place prize, and 1,465 votes were cast to narrow it down to our 12 finalists, whose recipes were baked and judged by Tribune staffers.
The winners are below, along with the stories of how their cookies came to be. It’s been a delicious pleasure, as always, to kick off the holiday season with a Chicago tradition more than three decades in the making. Happy holidays, and happy eating.— Ariel Cheung, food editor
Caroline Crispino: Chocolate Salted-Caramel Surprise Cookies
“It’s a chocolate cookie dough with a Rolo inside topped with flaky salt, which just truly brings out the saltiness in the caramel,” said Caroline Crispino, when asked to describe her first-place Chocolate Salted-Caramel Surprise Cookies.
Crispino speaks from a decade of experience with her recipe, which began with early disaster.
“The caramel I had made hardened too much,” she said. “And I was Googling caramel substitutes quickly.” Her search came up with Rolos, the roll-shaped chocolates with caramel inside, and they worked.
She also changed the finishing touch from kosher salt to Maldon salt when she happened to have some on hand. The artisan sea salt has long been prized for snow-white flakes.
“I put that on top and it was just so much better,” Crispino said. “When you can make it with Maldon salt, do it.”
The experienced baker and home cook has made variations of her recipe for years, and says anybody can bake it.
“The hardest part of this cookie is really unwrapping the 50,000 Rolos that you’ll want to use,” she added, laughing.
Crispino, 43, lives in Streeterville, and was just named vice president at Zeno Group, a public relations firm.
It’s a long way from where she started baking, and not just around the holidays.
“I grew up in Pittsburgh,” she said. Her dad came home one hot summer day to find his young daughter baking chocolate chip cookies. “He looked at me and said, ‘It’s 90 degrees outside and you’re running a hot oven?’”
But baking and cooking runs in the family.
“I’m Italian,” Crispino said. “My great-grandmother came over from Italy.”
The great-granddaughter grew up with people making great meals for their family, but the holiday cookie holds a special importance.
“Making a holiday cookie that people like is important to me,” she added. “I just love sharing recipes and making great food for people.”
Both of her grandmothers made holiday sweets, which she loves to this day.
“My maternal grandmother made buckeyes, and candied orange slices dipped in chocolate during the holidays,” she said. (Buckeyes are the chocolate-dipped peanut butter fudge named for the nut they resemble.)
Her late paternal great-grandmother, who emigrated from Durazzano outside of Naples, made pizzelles, traditional waffle cookies, and an entire Italian cookie collection, which Crispino says rivals anything you can get in Italy today.
“Especially her pignoli cookies,” she said.
Which got the baker thinking about next year’s holiday cookie contest.
“Maybe I’ll sign up next year and send in my pignoli cookie recipe,” she said, with another laugh. — Louisa Chu
Andrew Yohanan: Marbled Pistachio Almond Cookies
Crisp, crumbly and tender, these Marbled Pistachio Almond Cookies can be eaten while sipping a cup of tea in the morning for breakfast or the night before Christmas while waiting for Santa to come down the chimney, said baker Andrew Yohanan.
“This has been a holiday cookie for the past two years now, and my favorite because it looks very pretty without a ton of work,” Yohanan said. “It’s not as easy as a chocolate chip cookie, but it is easy for how good it looks.”
Yohanan was first inspired by author, chef and YouTube personality Claire Saffitz, who in 2020 shared her pistachio pinwheel cookie recipe.
“I liked them, but I had a few issues with them, so I changed them up a bit,” Yohanan said. “I increased the butter, added more pistachios and changed the shape.”
It took making four to five different batches to get the Marbled Pistachio Cookies just the way he likes it.
“They’re rectangular with crisp edges; a lightly golden and speckled almond dough contrasts the stark green ribbons of pistachios,” Yohanan said. “The cookies look like a perfectly wrapped present under a Christmas tree.”
In addition to swirls of pistachio-green, each cookie is “wrapped” with a red sanding sugar bow, adding to the festive aesthetic.
Between family, friends and co-workers, Yohanan guesses more than 100 people have tasted his recipe.
The DeKalb County resident works as a marketing strategies and insights consultant but considers himself a baker.
“I was the type of person who rolled into my apartment in my sophomore year of college with a stand mixer while most people just showed up with a mini fridge,” Yohanan said.
His love for baking began when he was about four years old. His earliest memories are spending time with his mother in the kitchen while she baked cookies for Christmas, pies for Thanksgiving and Texas sheet cakes for fun.
“I was doing a lot of the sampling though,” Yohanan said. “It’s evolved into me doing the baking and her doing the sampling.”
As for the Marbled Pistachio Almond Cookie, Yohanan hopes others will try his recipe this holiday season.
For those who are curious about making this dessert, Yohanan emphasized being careful not to overbake the cookie as it’s prone to drying out quickly and cracking.
“Watch very carefully for those lightly golden edges and you’ll have a perfectly moist, yet crumbly, buttery cookie,” said Yohanan. — Tatyana Turner
Christine Mayer: Decorated Snickerdoodle Sugar Cookies
Last year for Christmas, Christine Mayer wanted to try something new.
After searching online and finding a decorated sugar cookie recipe, the Evanston, Illinois resident and self-taught baker thought to herself, “these look so cute. How hard can this be?”
But when she first attempted, they didn’t turn out how she thought.
“I had no idea how to do any of the icing or decorating to make it look like something you would want to eat,” Mayer said. Since then, her decorating skills have developed tremendously.
A home-based baker of around five years, Mayer first submitted a recipe to the Tribune’s Cookie Contest in 2020, but didn’t place. Last year, she wanted to submit a recipe but missed the deadline. Finally this year, at her mom’s urging, Mayer submitted a recipe for her Decorated Sugar Snickerdoodle Cookies that earned her the third-place prize.
“I was looking for something kind of seasonal. And so snickerdoodle sounded really good,” she said.
She played around with snickerdoodle recipes until she found the right consistency of what is now a dense, chewy and sweetly spiced cookie. The key was getting the right balance of butter and flour for the dough to hold its shape once cut into a mold.
Now, her neatly embellished cookies are as nice to look at as they are to taste.
Mayer submitted a recipe with a photo of her cookies shaped like red trucks hauling green pine trees. Not only do they get her into the holiday spirit, Mayer said this design also allowed her to experiment with textures, such as sprinkles to imitate snow on the trees. Of course, home bakers can use any cookie cutter that stirs their inspiration.
“I’m not an artistic person in my everyday life,” said Mayer, who heads executive MBA admissions at Northwestern’s Kellogg School of Management. “But when I get to the cookies, you can have a little fun.”
Though a time-consuming task, Mayer said she gets a lot out of decorating cookies, baking for holidays, snapping photos of her creations and getting reactions from loved ones who enjoy her baking.
“The only problem is that sometimes people tell me, ‘Oh this is too pretty to eat,’ ” Mayer said. “And I’m like, ‘No, you better eat it. I spent a lot of time decorating it and making it really pretty. I want you to eat it.’ ” — Lauryn Azu