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Steve Caballero Calls It Quits on 365-Day Kickflip Challenge After 24 Days Due to Groin Pain

Steve Caballero taps out of 365 day kickflip challenge.
ShreddER September 7, 2026
Steve Caballero Calls It Quits on 365-Day Kickflip Challenge After 24 Days Due to Groin Pain
@Instagram.com/stevecaballero

As we previously reported, skate legend Steve Caballero took on a 365 day challenge that required him to land a kickflip every day for an entire year.

READ MORE: Skate Legend Steve Caballero Starts a 365-Day Kickflip Challenge & Calls Skaters to Join

Steve Caballero Starts a 365-Day Kickflip Challenge
Credit: The Platfrm; Steve Caballero

He also invited other skaters to join him and share their own attempts.

Caballero has now decided to stop after reaching Day 24 because of an injury to his left groin.

The pain started after he began skating every day for the challenge and eventually became too uncomfortable to ignore.

Rather than continue while injured, he decided to take a break and give his body time to recover.

Caballero explained the situation to his followers:

"Well... I gave it my best effort but I just can't handle the pain I've been feeling I sustained in my left groin recently since I started the @kickflipoftheday year challenge 😩 - sorry to disappoint, I made it to day 24 but the pain wasn't making this challenge fun for me anymore and I decided to give up and let it rest so I can heal to skate another day 😢 - the best part was it got me to skate everyday but not sure if that was a good thing for a grandpa 💁🏻‍♂️🤣
Thanks for following my short journey and commitment , I appreciated the love and support ❤️"

One thing Caballero did enjoy was having a reason to skate every day.

The routine kept him on his board consistently, although he admitted that doing so may not have been the best idea for someone he jokingly describes as a "grandpa."

After spending decades on a skateboard, Caballero has plenty of experience knowing when it is time to back off.

Continuing to skate through an injury could make things worse, so he chose recovery over completing the challenge.

So, the 365 day kickflip challenge ends for Caballero at Day 24.

The goal was ambitious, but getting back to skating without pain is more important than completing a daily streak.

View this post on Instagram

A post shared by Steve Caballero (@stevecaballero)

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