Squirrel Island Historical Society: Truck Guys
Mason Gillespie
I took the Truck Guy's job from 1998-2001. I began as the third guy in rotation working with Robby Knake and Brett Newbury. From 1999-2001, Mike Mazzone and I teamed up with Chris Wichowski. I took the job because I thought it was one of the best jobs the island had to offer for a teenager/college student. It was great being able to work outside and get to know the other island families that I hadn't had the opportunity to meet.

The biggest challenges were the bad weather days. It was, and still is, difficult to keep everyone's luggage and groceries dry. Not to mention getting them to their cottages in a timely manner. Also, there were more boats back then there are now. We often found ourselves finishing deliveries from the previous boat just as the Novelty was sounding its horn to inform us of its arrival. Rob had to ask us to "slow it down" from time to time.

Tons of funny stories, but I am sure I cannot share most of them as they are inside jokes. I will say that getting to know the off-island workers was a perk of the job. Not everyone can say they know and have great relationships with the guys cutting the soccer field lawn or fixing their lawnmower. I have great and lasting friendships with Brad Drummond and Tony Hyson. Those are relationships that I am glad I was able to build and will have forever. I am rarely on the island during the week these days but when I am, I make sure to seek them out for a conversation...and hopefully make it to morning coffee in the Farmhouse, if I am awake.

Squirrel Island is a great place to work. Rob will treat you with respect when you've earned and he will make sure you understand the value of hard work when it's all said and done. My parents and grandparents instilled a great work ethic in me but working for Rob helped make sure the work ethic grew.

During my summers as a Truck Guy there were a few new houses being built. The Barrett's had just bought and were remodeling the old Jessup cottage and the Farrington's were building their new home from scratch. Other than that, it was the usual "work hard and play hard" attitude that my friends and I exercised every night.