Here’s what a $1,000 cinnamon roll looks like! DeeDee Kennedy’s roll was the State Fair’s best!


DES MOINES, Iowa, Aug. 21, 2023 – A funny thing happened on my heralded return to the Iowa State Fair as the Czar of Cinnamon Rolls – I got scooped!

I just hope I didn’t get COVID.

My step-daughter Janae Jaynes, from Scottsdale, Ariz., arrived Friday evening for a visit.  She’d just been visiting friends in New York City.  My wife Mary Riche and I welcomed, hugged, shared dinner and sat around chatting in Des Moines with Janae and her friend Mark Herbst.  Late Friday night, Janae received a text message that one of their hosts in New York had tested positive for COVID.  Saturday morning, Janae and Mark tested positive, too.

We quickly conferred, realized we needed to isolate, and the last place we should go was the State Fair.  I called cinnamon roll contest sponsor & organizer Jamie Buelt, of Ankeny.

Here’s the champion in “The Great Cinnamon Roll Contest of 2023,” selected Saturday at the Iowa State Fair. The baker was DeeDee Kennedy, of Des Moines, as you’ll read below here. (Photo by Jamie Buelt)

When Buelt announced the contest months ago, she said she was sponsoring it “in support of Chuck Offenburger and his travels across Iowa looking for the perfect cinnamon roll.”   A couple weeks ago in a column here, I told the story about how nearly 40 years ago in my Des Moines Register columns, I had the whole state going crazy for cinnamon rolls as they followed my “Roll Poll.” You can read that recent column right here.

She scrambled, and found an excellent replacement judge for me – Des Moines City Council member & candidate for mayor Connie Fulk Boesen, who grew up at the State Fair when her dad Kenny Fulk was the manager.  Boesen joined four other veteran food judges.  Among them, they’d won more than 1,000 blue ribbons in State Fair food contests.

And then Courtney Crowder, one of my proteges as the current Iowa columnist at the Register, meandered into the Elwell Family Food Center looking for a story – and found a dandy.

In Monday’s Register, Crowder told the wonderful story of how DeeDee Kennedy, a Des Moines woman who’s been entering the State Fair cinnamon rolls contests for 15 years without ever placing higher than second, this time won the blue ribbon and the $1,000 in the contest’s championship prize money.  She and her husband Bob Kennedy were squirming nervously in the front row of the audience during the judging.

DeeDee Kennedy, as she appeared in a news clip on “We Are Iowa Local 5 News” on WOI-TV  right after the judging.

You can read Crowder’s column by clicking on this link, if the Register’s paywall will allow you access.  If it doesn’t, go buy a print copy of the Register – it’ll be worth it.

It’ll tell you how DeeDee Kennedy’s big win came in a baking season when she’s battling muscle cancer, which Crowder reported has returned for a third time, and for which Kennedy will soon be undergoing treatment at the Mayo Clinic in Rochester, Minn.

She told Crowder she doesn’t feel sick, and maybe increasing her baking has been helping with that.

In fact, she had a banner year at this just-ended 2023 State Fair, winning a total of seven food contests!  One of them was the other contest with a $1,000 first prize – a casserole contest benefitting the Iowa Food Bank. Kennedy’s entry for that one was a pasta dish she called “Holy Moly Mostaccioli.”  She donated that prize money back to the Food Bank.

If you wonder if there was some sympathy voting going on, forget it.  State Fair food judges do not know the identities of those whose entries they’re judging until after the contests are complete.

Those judges – especially the judges for this “Great Cinnamon Roll Challenge of 2023” – were looking for quality and special touches on frosted rolls.

“The recipe I’ve normally used is for what I think is just a nice, ordinary roll,” Kennedy told me when I called to congratulate her Sunday night. “I’ve made it for our family for years, and they like it.

“The thing that makes it a little different is that when I roll out the dough, most people would have it covering an area about 9 by 12 inches.  I roll it out to cover an area covering about 18 to 24 inches.  Then we cut it in 2-inch strips and wind them up pretty tight to form the roll.  If you cut one of my finished rolls in half, you’ll see about 10 layers of breading, and the judges always seem to like that.”

Bob Kennedy told me that he has two duties in the process: “I cut the 2-inch strips, and I wash the dishes.”

Jamie Buelt and cinnamon roll champion DeeDee Kennedy. (Photo by Gary Buelt)

But DeeDee Kennedy said she did one thing different for this year’s winning rolls.

“I added more cinnamon than I usually do,” she said. “Lana Shope is one of the best bakers in the area, and I’ve taken classes from her. (Shope, of Norwalk, was also one of the judges in the contest Saturday, but Kennedy did not know that beforehand.) When I was planning on what I was going to do this time, and thinking about what I could do differently, I checked one of Lana’s recipes that I have, and I saw that when I’d normally be adding 2 teaspoons of cinnamon, Lana was using 2 tablespoons of it.  So that’s what I did with the rolls that won this time.  But I was really nervous about it.  I kept asking other bakers there how much cinnamon they’d used.”

So here we are now:

–DeeDee Kennedy is beaming, as well she should.

–Jamie Buelt, a public relations executive who organizes State Fair food contests because she loves hanging out at the Elwell Family Food Center during the fair, says she’s happy that there were 42 excellent entries this first time she staged this “Great Cinnamon Roll Challenge.” And the actual judging attracted a big crowd of spectators, “70-deep,” as Crowder reported in the Register.  Buelt put up $2,000 of her own as prize money, which was spread through six places. She said the fair’s food officials are encouraging her to have it again, and consider adding a “caramel & pecan” division along with the “frosted” division, but that’ll require more prize money.

–I’m still sorry and pouting that I missed my own contest Saturday, so I’m hereby offering to buy my way back in next year by putting up $1,000 to add to Buelt’s pool of prize money, for however she wants to run the competition.

–We continued isolating at home, waiting for 72 hours after our exposure to COVID to take a test Monday afternoon. Mary and I were both “negative” in that test, so we cautiously resumed normal life. If we’d been “positive,” we were going to stay home and pout some more.

Meantime, all you out there keep me informed on good cinnamon rolls you are finding in cafes and bakeries around the state, as well as good at-home bakers you know.  I may well resume the “Roll Poll” in one form or another.  It’s clear: Iowans still love their cinnamon rolls.

The top four placers in the cinnamon roll contest with sponsor Jamie Buelt (center). Left to right are Alisha Ruffcorn, of North Liberty, 4th; Meredith Melchers, Cedar Rapids, 3rd; Buelt; DeeDee Kennedy, 1st, and Susie Jones, Winterset, 2nd. (Photo by Gary Buelt)

All the best rolls at the Iowa State Fair. (Photo by Artis Reis)

You can comment on this column below or write the columnist directly by email at

2 thoughts on “Here’s what a $1,000 cinnamon roll looks like! DeeDee Kennedy’s roll was the State Fair’s best!

  1. Chuck – what fun I used to have trying to get you to declare my “chocolate” cinnamon roll a winner . At least you got to feast on mine at Christmas time when you sang in the choir at St Mary of Nazareth in Des Moines. You have always been my favorite columnist and thanks for keeping me on your facebook list because I read eveything you send.

    • City - DM
    • State - Ia

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