Sides rejoined the World of Outlaws in 2007, but four years later he was involved in controversy after he competed in an unsanctioned event.
“It was a race promoted by the Schatz family,” he said. “I called Brian Carter and he couldn’t talk at the time, but said he’d call me back the next morning. He didn’t ever get back to me, nor respond to multiple texts. Donny Schatz and another World of Outlaws driver raced, so we decided to compete as well. The next race we showed up to I was informed that I would be penalized in tow money, pit passes and points fund.”
Sides sued World Racing Group and the case was settled in 2012.
“I guess it’s something you’re not supposed to talk about, but I don’t really care,” he said. “I will say the only people who came out on the positive of that were the lawyers.”
It was around that same time period that Sides got divorced and in January 2014 the biggest obstacle of his life occurred when his father, Larry, died suddenly.
“He was my best friend,” he said. “He picked us up from the airport that Tuesday night as we got back from Australia. He drove us home and said we’d get lunch the next day. He called at 10 in the morning, but I missed the call. I got over there at 1 o’clock and found him dead on the floor. The pacemaker was still going because he’d already had a couple heart attacks. My brother, Paul, lived next door so I ran over there and Paul did CPR until the ambulance arrived, but he was gone.”
Sides has seen his fair share of tragedy and setbacks, but one of the consistent characteristics throughout his life has been a positive outlook. Despite the challenges, at the end of the day he gets to live out a dream that he relishes.
The reality of transitioning out of the driver’s seat began last year when Sides put veteran Tim Kaeding in his No. 7s for several races. It was a success as Kaeding produced seven top-five finishes, including a fifth-place result during the Knoxville Nationals at Knoxville (Iowa) Raceway.
Sides and Kaeding are teaming up for approximately 30 races this year.
“I actually had someone who was going to drive for me this year, but it fell through financially,” he said. “I was going to stop racing and put someone in the car full time and then have a second car for Tim. I don’t know exactly when I’ll be done driving. It could happen this weekend, next week, a year or two. When it happens that’s it. There won’t be a farewell tour. I still enjoy working on them, playing on them.
“I’d like to have some kind of business, something that can make money without having to be there every single day,” Sides added. “I don’t have that luxury. Many of the drivers who set up businesses drove for somebody and could go home during the week. I drive the truck, wash everything, do the maintenance. I don’t have that option so I just wing it. If something happens I’ll figure it out.”
Regardless of the ups and downs, the roller-coaster ride of Sides’ career is something he hasn’t taken for granted and it will likely end with him wearing the same welcoming smile and drinking a beer or two — or five.