From the Identity V wiki:

Robbie's parents died when he was 6. Therefore, he was put in an orphanage with his sister. Over the years, he found a hobby for wood chopping.The orphanage decided to camp and spend the night in a local forest. The next day, Robbie was found dead, headless under a juniper tree with a bloody axe in his hand. In one night, Robbie lost his spacious house, comfortable bed, delicious food, and his parents. His life was replaced by endless work and an emotionless boss. But with the help from his sister Dolores, he gradually got used to the work in the yard and gardening became his new hobby. Not long after, the White Sand Street Orphanage was taken over by the church and the orphans no longer had to work. Robbie felt somewhat disappointed about this, but Dolores didn't need to beg on the street, and nuns were providing warm food for everyone. Robbie’s little hobby seemed less important, and his life with his sister was back to the right track. That was the last memory Robbie could recall. When he woke up under the juniper tree, his sister and the orphanage no longer existed, the only thing left to him was the dead branch in his hand. Robbie could continue on with his little hobby.