Bruce Gray, a dear friend and copywriter I’ve partnered with for years, approached me with a project to help his brother commemorate the 90th anniversary of his boat, the Fishing Vessel “Little Lady” – the oldest one-man wooden dragger still in service in all of New England. Proceeds from this effort will help preserve her now and into retirement.

Roll: Art Director Copy: Bruce Gray


She was built in Mystic, CT in 1929.

A side dragger, with a snub nose. In 1931, she was bought by Leonard Jason. He was 22, first-generation from a family in Faial Island in The Azores. First thing he did was cut that nose off. The new bow added about three knots to her clip.

Captain Lenny fished The Little Lady out of Menemsha until 1970, when his youngest son Dennis took over. He fished her for the next few decades, before turning the reins over to his son Denny in the early 2000’s.  

This year marks her 90th dragging for Fluke and Flounder. Beyond the “new” bow and occasional winch rebuild, the boat looks and sounds just as she did that first summer. 

The F/V Little Lady is the oldest one man, wooden dragger still operating in New England. She’s held that title for a lot of years now.  And she’s still got a few good ones left.


We landed on a simple, heroic design that accurately mirrors the boat’s iconic lines.