Oldest tool you regularly use?

8in Bet-R-Grip by J.P. Danielson Co Inc Jamestown NY.

Somewhere along the way, I stole this from my dads toolbox. Since it was in my dads box, I'm sure it belonged to my grandpa before that. Best that I can tell is it came from 1933-1938. I used them on the regular. It is the best adjustable wrench that I have. I also have a Crescent 12in which I'm assuming is from the same time period or about.

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I have an off brand (cheap) 3/8 wrench that I used when I built boats for a living at Post Marine and Sieldleman sails. The wrench got a 3M 5200 sealant on it that remains to this day. It held up 30 years before all of it was off the face of the jaws. Shout out to 3M 5200. They are still my go to 3/8 and sealant.
https://www.3m.com/3M/en_US/p/d/b40066983/
 
I am assuming this was for a lawn mowing business? That would have been a significant purchase for a 13 year old in 1984.

Lawn Boys weren't the cheapest option out there.
I have used them a few times and I liked their quirkiness.
At that time, they were vastly superior to the competitors….at least that was my perception. Would love to have that staggered front wheel setup today.
 
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