(1856 - 1929)
Orlando attended school in Gloucester and after completing his education, he entered into the fish business when he joined then firm of Rowe and Jordan.
In 1909, after making sure he was financially stable, Orlando married Charlotte Jane Gray, to whom he had proposed three years earlier via a five page letter.
In 1914, five years after the death of Charlotte, he married Mary Garland Wonson.
He and Charlotte had one child:
|Roy Douglass||1887 - 1951|
He and Mary had one child:
|Miriam Wonson||1917 - 1993|
After being with the Rowe and Jordan firm for a number of years, he became the confidential clerk to Mr. Jordan. Eventually, this firm was reorganized and continued business under the name of the William H. Jordan Company, and in January of 1903, Mr. Jordan admitted Orlando as his partner in the shipping business.
About three years before Orlando and Charlotte married, he wrote her five page letter of proposal. In the letter, he explains his intentions, what he hopes for in a marriage ... that he is looking for love, not just a home to return to after work. He also makes it clear that he understands she may not want to wait so long, but that he does not wish to marry until he is financial stable. At that time, he believed it would take him three years to achieve that goal.
Clearly Orlando had a very serious plan for making sure everything would fall into place so he and Charlotte could marry. By the time of their marriage he had a very secure and responsible postiton with the W. H. Jordon & Company fish firm, and eventually became the treasurer of the firm.
The orignal copy of this letter still exists, and was returned in the fall of 2015 to part of Orlando's descendants.