I introduced Jigsaw Trouserdrop on August 20, 1998. The design was derived from my Blue Highway typeface. A friend suggested I create a jigsaw puzzle font, which led me to experiment with adding puzzle-like forms to the letters. An early version included small caps, though I removed them in later releases. The name was chosen spontaneously and had no particular connection to the design.
I originally distributed Jigsaw Trouserdrop with a free commercial-use desktop license. In August 2020, I placed it in the public domain.