Former Pro Cyclist Phil Gaimon’s “Worst Retirement Ever”

Late last year, Phil Gaimon made a decision. “I couldn’t be the best at cycling, so I decided to be the worst at retirement.”

The “Worst Retirement Ever” has Phil chasing Strava KOMs around the U.S. and the world as he provides a real-world answer to “what if an actual cycling pro tried this segment and didn’t hold back?”

What started as an effort to displace a known doper from the top spot on the leaderboard for some iconic Los Angeles-area climbs became a popular YouTube series following Phil as he puts his recently-pro-level skills up against the reigning KOM champs.

He’s quick to point out that there’s nothing particularly special about him, and that a lot of other pros could totally annihilate his records–they just have better things to do. The subtle message of the series to stop taking Strava way too seriously is conveyed by Phil taking KOM attempts to a patently ridiculous level (including wearing a speed suit, riding a custom Cannondale bicycle, and sometimes removing items like brakes to save a few grams).

No discussion with Phil would be complete without a lengthy discussion of cookies. The moniker “Cookie Monster” was given to him during his pro career, and he makes finding a good cookie (worth spending calories on) a mission worthy of a ranked list on his website.

The cookie craze has ballooned into Cookie Corners as races such as the Tour of California to promote his Cookie Fondo.

Check out Phil’s books:

Draft Animals: Living the Pro Cycling Dream (Once in a While) 
Releasing October 207.

Ask a Pro

Pro Cycling on $10 a Day


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