The Guess family made quite an impression at the recent Oklahoma Trucking Association’s (OTA) Championship, an annual contest of professional trucker skills. Father Richie won the championship in the 4-axle division, daughter Tiffany placed first in the step van division, and son Cory, who was competing for the first time, placed second in the step van division. All three work for UPS. They will be competing in the National Truck Driving Championship, a “virtual” online competition on July 31 – Richie and Tiffany as first place winners and Cory as an alternate, since he placed second.

Richie is obviously very proud. He has worked for UPS since he graduated from high school in 1983. Tiffany began working part time for UPS while she was earning her degree from OU and now works full time. Cory chose to go to work for UPS instead of attending college after he graduated from high school. A middle child, Zachary, is also a truck driver working for Dolese.

“My wife works for a bank. She’s the only one in the family that doesn’t drive,” Richie says with a laugh.

Richie states he grew up in Sasakwa. Georgetta Guess is his mother, and his father was the late Richmond Guess. Sasakwa is where he learned to drive in the hayfields at an early age, stacking square hay bales in a horse trailer and hauling them to the barn to unload. It was hard work, but he always looked forward to it. His three children all learned to drive the same way.

After Richie graduated from Sasakwa High School in 1983 his uncle in Oklahoma City informed him UPS was hiring and invited him to stay with him until he could get on his feet. Richie began working part time at night from 11:00 p.m. – 3:00 a.m. while attending college in the daytime. Even though UPS paid well, it was only part time work. Even after he took on another part time job at a bar-b-que restaurant, he still didn’t have much money to spend after paying his bills, but he got by.

Richie began working at UPS full time when he was 25, the same year he married his wife, Stephanie, and they had their first child, Tiffany. After driving UPS step vans for seven years, he moved up to “feeders,” the larger semi-trucks that move the packages to the distributors. He now drives “twins,” a semi-truck hauling two trailers.

When he first learned about the Oklahoma Trucking Association’s annual contest that tests truck drivers’ skills, he was reluctant to compete, because he was afraid the other drivers would laugh at him, However, once he tried, he saw that it wasn’t that much different than what he was doing every day on the job. It just looked different set up on the track.

Ritchie states that after the first competition he was hooked. He has been competing for 15 years, and this was the fourth time he’s won the competition. He won grand champion in 2013 driving twins. In 2014 he placed first again driving twins. The OTA rules state that, after winning first place two years in a row you can’t compete in that same division again, so he sat out the next year. He won first place again when he competed in twins in 2016. This year he tried something different and won first place in the fouraxle tractor-semitrailer division. Richie states that, for him, pulling twins comes easier that pulling a single trailer. In addition to twins, step side, and four-axle, the other divisions are threeaxle, five -axle tank, fiveaxle van, five-axle flatbed, and five-axle sleeper.

Richie explains that Tiffany was working two part time jobs while attending school when his barber suggested she should work part time for UPS, too. Richie was surprised he hadn’t thought of it, but she tried it out and enjoyed it so much she was ready to go full time, but Ritchie convinced her to finish her degree before going full time. This was her fourth year competing, and she has previously won second and third places.

When Cory graduated from high school, he told his dad he wasn’t interested in attending college. He wanted to go to work for UPS immediately. He was able to start part time, and eventually worked his way up to full time. This was his first time to compete in the OTA contest. While he has the same competitive spirit as his dad and sister, he clarifies that he participated in the championship for the fun of the challenge and to be around the other drivers. He explains the family has always been close, and he talks to his sister every day. Now that they’re doing the same thing, they have even more to talk about.

Tiffany recently earned her CDL license and has started driving the larger semi-trucks. Cory has now also passed his CDL test and will soon be driving big rigs, too. The pride in Richie’s voice when he shares this information is obvious. He is thrilled that they both also enjoy the competition as much as he does, and he is delighted to have them compete by his side.

Richie concludes that if there is any lesson to his story, he wants kids to be aware that most people don’t start at the top. They may see him buying a new truck and wonder why they can’t buy one, too. He points out that he paid his dues when he was working two jobs and attending college, driving a 1973 Maverick instead of a new truck.