Bob was the younger brother of Bruce. Bruce was a founding member of The Midnight Society. When his older brother
was just a teenager, he somehow immediately obtained the full ownership of an entire amusement park. He was aware that his brother and his friends had used a magical item none as The Silver Sight, unaware until it was too late that it was evil. So Bruce hid it inside the amusement park.
Then Bruce warned him that, if anything should ever happen to him to wait and give instructions two or more people at one time. Therefore it wouldn't look suspicious with just one person wanting the item just for himself or herself. Bruce gave him instructions on how to find out where he hid a clue.
The day after his brother hid the Silver Sight, he died. His brother died falling down from a rolling coaster trying to fix a cable. But he had hunch that it was no accident, since it was Bruce's favorite ride, which he knew like the back of his hand. So he has a feeling that someone or something pushed him.
After his brother passed away, ownership of the amusement park was passed down to him. Which he continued to run for the rest of his life. He never had the heart to close the park or retire, because the park reminded him too much of his dear brother.
Then in the year 2000, the Evil Demon linked to the Silver Sight conjured up again. After it scared Grandpa Gene to death, the current Midnight Society knew they had to track down the Silver Sight and destroy it once and for all. So Andy and Vange seeked him out and filled him on the situation. He trusted them and give them the clue his brother gave him. He was very surprised it lead to the inside of the well at the old house that he and hid brother grew up in. Andy and Vange successfully found his brothers clue and retreated with their friends.
He soon joined with Vince (an old boyfriend of Donna), Mr. Gregory (Eleanor's son) and Grandma Aggie (Gene's wife) late at night in Playland Amusement Park to support The Midnight Society in their quest to destroy the silver sight. He then witnessed, Gary making the right choice of knowing who their true enemy was and banished The Demon who was rightfully the true enemy all along.
- Walter Massey also portrayed Grandpa Samuel in the episode "The Tale of the Room for Rent"