Cartoon Caption Classic Winner Surprised by Her Success

Christen Whalen has a lot of thank-you notes to send.

The winner of our Cartoon Caption Classic said she employed no particular tactical strategies to amass the 593 votes she collected in the final round, when her caption idea topped that of our other finalist, Graham Gillespie, who had 556.

“I really honestly didn’t expect to win,” said Whalen, of Hermitage, Pennsylania.  “I guess maybe my colleagues and family [account for her success] because I e-mailed them every week, and I found out they were sending it out too.”


Whalen and Gillespie advanced through the four-week contest by providing captions that earned support from readers. The original field of 17 was trimmed to 12, then six, then the two finalists.

RESULTS: Week One | Week Two | Week Three

Both Whalen and Gillespie had participated in Transport Topics’ 2016 weekly Cartoon Caption Contest. Whalen, an administrative assistant for Matson Logistics, said her father saw the contest in Transport Topics and encouraged her to participate. She won the Week 8 contest. Gillespie, of Ajax, Ontario, won Week 31. Those weekly winners were invited back to participate in the 2017 Cartoon Caption Classic under an elimination format.

Whalen's winning caption

Whalen said she had forgotten about competing in this year’s event when she received a reminder email from Transport Topics very close to the deadline. “I wrote up my captions really quick, on the spot, and submitted them,” she said. She said she didn’t solicit voting support on social media because she wasn’t confident in her entries.

Despite her low expectations for winning, Whalen said she’s always been told she has a good sense of humor. “People will say some one-liners and I’ll come back with some,” she said. “At my family get-togethers there’s always a whole lot of laughing. That’s the environment I was kinda raised in.”

That environment carries over to her small four-person independent office in Girard, Ohio, where her father Rick is president of Dina-Lind Enterprises, which acts as a broker for Matson Logistics. Whalen has worked there for two-plus years.

She has a 6-year-old son, Rylan, who clearly is the light of her life. “I had him when I was in college, and he changed everything when he came along,” she said. “No matter how tough of a day I’ve had, when I pick him up at school, nothing else matters.” They enjoy squirt-gun battles and hiking, and have recently taken up fishing.

Gillespie, a logistics analyst and customs specialist with Active Exhaust Corp. in Toronto, had garnered the most votes of any contestant in Week Three to earn his spot in the finals, and that tempered Whalen’s expectations too. “When I saw the results from last week, I saw he (Gillespie) had a lot of votes, so I thought I had a 50-50 chance,” Whalen said. “But I just prepared myself to lose, so I didn’t get my hopes up.”

But thanks to those friends and family and voters in general, Whalen can lay claim to the title of trucking’s queen of caption writing. As champion, Whalen will receive a special commemoration of her achievement that showcases her caption-writing talents, as well as a Transport Topics prize package that includes a subscription and a $250 gift card. Runner-up Gillespie will be awarded a $50 gift card.

Whalen's Week Three entry

Whalen's Week Two entry

Whalen's Week One entry