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    You are at:Home»Trucker Talk»Three Generations
    Trucker Talk

    Three Generations

    By John & Kim JaikesJuly 1, 2025No Comments9 Mins Read
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    When you’ve been on the road for over four decades you know a lot of people.  The odds of meeting up with someone you knew back in the early days of your career gets less and less as the years go by.  Four years ago, while at the Waupun Truck-N-Show, I started up a conversation with Wyatt Sperry.  His dad Chris had entered his truck in the show and Wyatt had polished it.  While we were chatting, it finally clicked – I looked at his thick red hair and his last name and put it all together.

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    Back in the late 1980s, when we were driving for Freymiller, I was in Chicago and our friend Roger “Big Red” Sperry’s engine blew up and he needed a ride back home to Wisconsin.  I still remember that trip – my sister-in-law was running with me that week and we were able to help Red get home.  He was able to help us, as well.  My reefer ran out of fuel, and he helped me get it primed and running, so I could go load cheese.  Helping each other was just the way we rolled back then.

    Wyatt went over to his dad after our conversation and asked him who Big Red was.  Chris told him that it was his grandpa (Wyatt had never heard him called that before).  Later that night, Chris called his dad, and we got to reminisce a little about way back when.  We compared notes on old friends and if we knew where they were and, sadly, some have passed away.

    Roger Sperry, Wyatt’s grandfather, had a construction business he worked at during the day and he would haul loads of cattle at night to Madison, WI, Cedar Rapids, IA and Milwaukee, WI.  He was even a county sheriff for a while before he went from enforcing the law to bending it a bit sometimes.  To supplement his income as a dairy farmer, Don Freymiller began his driving career as a short-haul cattle trucker in Shullsburg, WI.  He started out with one truck and a vision and built it to a company of over 800 trucks when we were there.  One day Don asked his friend Roger if he was looking for a job, saying, “I have a truck for you.”  And the rest is history.

    Roger lease purchased a 1980 K-100 single bunk cabover Kenworth, powered by a white not yellow 3406A CAT engine, from Don, and then hit the road, pulling a refrigerated trailer, running from Wisconsin and Chicago to California.  We had a few friends who got their start at Freymiller in their lease purchase program and then went on to become successful owner operators.  The fleet was made up of cabover Kenworths, in the early days, before they converted to Freightliners.

    There was a group of drivers from Wisconsin, Illinois and Iowa that would regularly run together and oftentimes see each other at the terminal on Union Avenue in Bakersfield, CA.  While we were talking, Roger remembered Don had a few cars for the drivers to use when they were at the terminal so they could get something to eat, do laundry or get supplies at Walmart.  The hand tooled leather logbook covers that Freymiller awarded to their “drivers of the month” are beautiful, and Roger still has his, as he never used it, keeping it in the pristine condition he received it.

    Roger worked for Freymiller from 1981-1989 when he parked the truck and went back to the construction business.  In 1988 he decided to cover over the Freymiller blue with a coat of gray paint and “Old 807” got a new look for the last two years she ran there.  The white rims got a coat of gray paint, as well, until the winter that year when she got aluminum rims – she was walking in tall cotton.

    Roger, Chris and I shared some good memories of what it was like back then.  Different truck stops offered a free steak dinner with an oil change.  We all had our favorite places to stop along the way.  Some of the places we went were not so much fun like the Chicago Water Market, of course, in Chicago, and Kurt Van Engle Produce in Milwaukee, WI.  I remember making check calls to this one and he did not like women.  I always said, for those of us who ran team, that we were half the reason his freight got delivered on time!

    Bosselman’s in Grand Island, NE was a popular stop, especially when they had their prime rib buffet on Saturday nights.  Roger said he still likes to sit and talk to people.  It’s not as easy as it used to be, but sometimes you can strike up a conversation with a few drivers and take a little trip down memory lane.

    In 1991 Roger got a conventional Freightliner for his son Chris and wanted to lease it back on to Freymiller, but their insurance wouldn’t cover Chris, who had just turned 21.  At the time, Packerland would insure Chris, so they leased the 1986 black Classic XL with a 50” flat top bunk on with them.  She had a B-Model CAT, a 13-speed, and straight pipes that dad hated on the occasions that they got to run team.  Chris said they worked hard but had a lot of fun.  He had been riding with his dad, and in his younger years, he basically grew up in a truck.

    Running the old cabover local for a while, Roger eventually put her in the weeds.  It needed a fuel pump and some other work and at the time they didn’t think it was worth it.  He bought a 1995 T600 with a 3406E CAT and a 13-speed to haul grain locally.  It was an old Millis truck and funny thing is he still has it and it’s the truck he still runs today.  When I asked Roger if he just runs local now he said, “No, it’s long haul or nothing.”

    In 1998 Chris bought his first milk route and in 2003 he got his own authority.  But he got tired of the same old routine and got back on the road in 2005.  His dad put him back to work in a new 2006 white Peterbilt with a coffin bunk, hauling Dean’s Foods products east.  This truck was Wyatt’s introduction to trucking.  Getting strapped in the passenger seat in his car seat, he got to follow his dad’s baby steps and cut his teeth riding in a truck with his dad.  One time Chris remembers being in Big Springs, NE and Roger happened to stop there and parked next to him.  When Wyatt looked over and saw his grandpa he asked his dad, “How did grandpa find us so far from home?”

    In 2008 Chris was at home and he needed to move a trailer, and the only option was that old gray cabover out in the weeds.  He jumped the batteries, and she started, and after a little bit of work with parts they had laying around, they brought her back to life and she got to get out of the weeds and back on the road.  She was a work in progress for a couple years and even got to stretch out to a 240” wheelbase.  In the spring they haul starter kits for honeybees from California to Wisconsin, Kentucky and Ohio.  They revamped a reefer trailer with fans to pull in the fresh air and keep the circulation going.  They’ve been doing this for about 15 years.

    One might think that after riding in a truck, Wyatt would go down the same road as his grandpa and his dad, but that’s not the case.  When he was young, Wyatt was always treated like a little man and hung around the older guys.  At about five years old, there was a local polisher that Wyatt admired, and at eight years old he got his first buffer kit.  When he was 13, Wyatt went to work for him, and by the time he was 15, he started making his mark on the truck show scene with some amazing polishing skills.

    Taking pride in the job he does and the shine he puts on whatever he polishes, Wyatt can buff a truck out to a mirror finish, but he can drive it, too.  Although driving is not the road he chose, Wyatt recently bought his first truck.  After hounding the owner for nearly a year, he finally gave him a price, and the truck is extra special because it’s “Old 807” – his grandpa’s 1980 KW cabover, which had been parked in the shop, taking advantage of a little retirement, since 2010.

    With plans to leave the faded gray paint job with bits of Freymiller blue peeking out here and there alone, Wyatt does not want to strip her down and cover her with some pretty new coat of paint.  The interior has always been maintained, so it’s being left pretty much the same, too.  She did get a new retro steering wheel since the original one was cracked from age, and Wyatt put his magic buffer to the wheels.  His plans are to let her strut her stuff at local parades and truck shows.  Like this old truck, Wyatt and his dad and grandfather can share three generations of miles and memories, and we sure enjoyed being a part of it – and sharing some of ours, too.

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