The Boy who Jumped off Roofs
...and the man he became
Many men, when entering the stage of life we refer to as the “midlife crisis”, purchase things like sportscars or a motorcycles. By the time I began to dip a toe into my own midlife crisis I already owned a sportscar and a motorcycle, so I bought a skateboard.
I was a teen in the 1980s when skateboarding experienced a big resurgence. Gone were the old plastic skinny skateboards of the 1970s. Our skateboards were wide with curved tails and radical graphics. I owned a series of hand-me-down and no name skateboards as a kid until, for my fifteenth birthday, I got a real honest-to-goodness professional skateboard. I still remember all the details: it was a Fred Smith III model by Alva, with Tracker trucks and Slimeball wheels.
I gave up skateboarding around the time I graduated high school, which means I hadn’t been on one since approximately 1991. Doing the math, that means it had been more than 25 years since I’d stood on one. That didn’t stop me from buying another one. This time I bought a Steve Caballero model. Caballero was an influential skater from my era (he invented many tricks and some are even named after him). I even had a Caballero poster on my bedroom wall. I was a fan of his long before he was a playable character in Tony Hawk Pro Skater.
Needless to say, I didn’t do much skateboarding as an adult. I’ve had that Caballero board out in my garage for over a decade and if the thing had an odometer, the distance it has rolled could be measured in feet. Two digits, tops.
Not long after I purchased that skateboard I developed back problems. When I was 25, while walking down the side of the interstate after running out of gas I was struck in the back by a passing pickup truck doing 70mph. It was a glancing blow that sent me flying through the air, but after a few hours in the local ER I was sent home with just a few stitches, a bruise the size of a medium pizza, lots of swelling and, apparently, lingering back pain. Yay!
Compounding the issue was a diagnosis a few years ago with spinal stenosis, a fun condition where calcium builds up in the spine and puts pressure on (or constricts) spinal nerves. After a couple of MRIs and a meeting with a b spine specialist, I was given two options: I could take back pills three times a day, or they could perform surgery. The specialist spent the next five minutes describing a procedure in which my chest would be cut open, all my organs would be removed, the calcium deposits would be removed from the front side of my spine, everything would be put back into my chest and I would be stitched up.
I currently take three back pills a day.
For the record, if I hadn’t told you any of this, you would never know. I don’t walk hunched over or complain about anything. My doctor said I should sit when I can and not lift anything heavier than a jug of milk (note: that’s 7lbs; I break that rule daily) and hope the back pills keep working. We all hope the back pills keep working.
So in the middle of all this nonsense, my spine doctor asked me if I’d had any back injuries. I told him I’d been hit by a truck once and he barely raised an eyebrow.
“Anything else?” he asked. For the record, spine surgeons (a) are always in a hurry and (b) have no sense of humor. I’m generalizing; I don’t know if all spine doctors are like that. But I know one is.
“I used to jump off roofs,” I said.
That got his attention.
First of all let me just say that the 80s kicked ass. All that stuff you hear about parents not knowing where their kids were or what they were up to is 100% true. Every summer day I would eat breakfast, get on my bike, come home for lunch — or have lunch at some other kid’s house, as long as I called home — ride my bike some more and go home when my mom turned on the porch light. Today, kids can’t ride anything with wheels without wearing a helmet. I used to mow my backyard when I was 10 without a helmet. Or a shirt. Or shoes.
I don’t know why kids are always jumping off of things. Our local movie theater had a long row of steps leading up to the ticket booth and my friends and I would see who could jump all the way down from the highest step. We were always jumping off of things. One day we figured out that my neighbor’s stockade fence met up with the lowest point of their roof which allowed us to climb up on their roof with very little effort.
Roofs are weird. When you’re a kid, climbing onto a roof for the first time is a world-expanding experience. I remember climbing up on top of my neighbor’s, pulling myself up by placing my palms on gritty shingles and hearing my jeans drag across what felt like sandpaper. Roofs are steeper than they look from the ground. Your ankles and knees are always bent. From a roof, you can see into other people’s yards and look into trees. It was a brand new view of my small world.
The old expression “what goes up must come down” applies here. Transitioning from the roof back to the top of that wooden fence was a bit like a trust fall with no one there to catch you and so the best solution we found was to simply jump.
And so that’s what we did. We would sit on our butts and scoot all the way to the edge of the roof. With our legs dangling over the edge, we would give one good shove with our hands and literally take a leap of faith. We would hit the ground feet first and either roll to the ground or simply let our knees take the brunt of the impact. My knees hurt just typing that.
A couple of years ago I hurt my back while stepping off a curb. I was walking out of a grocery store, stepped off the curb, and it felt like someone had shoved a cattle prod up my butt all the way to my brain. And not in a good way. This led to a second round of MRIs and X-rays with a diagnosis of “hopefully it gets better.” It did, after a few weeks.
For the record, my spine doctor does not recommend jumping off of roofs.
Neither do I.
Steve Caballero is still skating. He recently turned 60 years old.








“All that stuff you hear about parents not knowing where their kids were or what they were up to is 100% true. “ 🤘 Yup! I did some seriously stoopid shit as a kid, although no skateboarding or roof jumping. Both my brother and I had lost our front teeth by age 17.
Holy shit, man, your poor back! May the back pills ALWAYS work!
My buddies and I had the great idea to jump off my parent’s garage roof and into our above ground pool. We survived and so did the pool! So then we got the bright idea to take my sister’s Big Wheel and jump off into the pool. Success! Was great fun until dad got home and caught my buddy mid jump. 🤣