Gerald Darlington was an executive at the Hamilton Watch Company; Kathryn was a secretary. How they got together, we can only speculate. We do know, however, there was some acrimony between Gerald and the board of executives because he wrote them several angry letters, and kept copies for himself.
Rumor has it Gerald reported the company to the IRS for not paying taxes, and the IRS offered a reward – err, incentive – of 10% of the recovered amount. Note that I have no way of substantiating anything in here, it’s just what I was told, please don’t sue me. All I know is that Dawn’s grandparents suddenly had a large amount of money, left the watch company, and bought Speedwell Farm. This was in 1941, just before we entered World War 2. Kathryn became a real estate agent, and Gerald became a magistrate.
There is a nice history of the watch company here. As an interesting aside, Hamilton went on to introduce the first electric watch in 1957, the first digital watch in 1972, and the first calculator watch in 1975.