Yoshi is obviously a descendant of another elf named Yoshi, who was one of the First 50 Elves, and of Yoshi's wife, Tamlyn. However, the cattle ranch which his family has run for the last few generations was inherited when the original Yoshi and Tamlyn's son, Desmond, married Bryna, the daughter of Corbin and Marissa, in 797. Bryna's younger brother, Eugene, had no interest in ranching, instead becoming a miner, like his mother. And so Bryna eventually took over her father's ranch, along with her husband, Desmond. When Bryna and Desmond's youngest child, Marilla, married a man named Finlay in 828, they followed the relatively new trend of adopting a surname based on one of their ancestors among the original elves. History does not record the reason they chose the name Des'Yoshi, after Marilla's paternal grandfather. However, it is seen by some as mildly ironic that Marilla's cousin, Alexandria (daughter of Eugene and a woman named Minerva), and her husband, Harrison, chose the name Des'Corbin, after Alex's own paternal grandfather, considering their branch of the family wasn't involved in running Corbin's ranch.
Yoshi Des'Yoshi is a member of the sixth generation of elves. He grew up on the family ranch, and was content to make a career of it, as his family had done for generations. He married a woman named Liliana in 893, and in 894 they had a daughter named Mia. In 896 they had a daughter named Ariadne. In 902 they had a son named Phileas. In 905, at the age of 37, Yoshi unexpectedly decided he was bored with ranching. This decision apparently came as the result of Woodstockade suddenly finding itself part of a larger inter-village community, upon the establishment of the Second Order. And so, he became a trader, traveling to various human villages to sell whatever elven goods might be of interest to humans, and buying human goods to sell back in Woodstockade. His new career began after traveling to Ristar, where he commissioned the construction of a galleon-class trading vessel, which he named the 73 Skidoo.
In 912, Yoshi was among the founders of a group of elves who came to the decision to settle a new village on the Isle of Freedom, believing there was a certain inequity in the fact that humans had so many villages, and elves only had one. When an announcement was made concerning the arrest of a certain group of alleged rebels called The Chaos, including an elf named Emma Pseud, Yoshi and his associates began thinking about the possibility that the village they founded might declare itself independent of the Second Order. During the Chaos War, Yoshi and the 73 Skidoo fought on the side of the Chaos, joining the fleet of Admiral Alphonse Teach at the Battle of West Ocean. And when Freeport was founded in 913, shortly before the establishment of the United Villages of the Chaos, the village's settlers voted to join the UVC. In the same election, Yoshi was voted Freeport's first Mayor. At that point, he gave the crew of the 73 Skidoo the option of carrying on as a trading vessel or joining the Chaos Navy; the crew chose the latter, and the 73 Skidoo became the flagship of the Freeport fleet.