Clayre Kay-Kay M. (Gaskill) Cataldo, 77, of Billerica, MA, died on Friday, January 13, 2017 at Lahey Hospital in Burlington, MA after a period of failing health. She was born on July 10, 1939 in Allston, MA to Albert and Elizabeth (Milley) Gaskill. Clayre was raised with her sister in Allston, MA. She played softball in high school and enjoyed being outside. She graduated from Brighton High School in 1957. After graduation Clayre found work with the John Hancock Financial Company where she met Anthony Cataldo. The couple married on October 15, 1966 at the St. Peters Catholic Church in Malden. Clayre worked her entire career at John Hancock retiring in 1989. She enjoyed long weekends in Atlantic City with Tony and spending summers at Harveys Lake in West Barnet, VT. She was an avid reader and enjoyed puzzles. Clayre is predeceased by her parents, an infant sister, Ann, a sister Marjorie McLeod, a nephew Brian McLeod and great- nephew Jordan Smith. She is survived by her husband Tony and niece Pamela McLeod Smith and 5 nieces and nephews. Interment will take place in the spring at West Barnet Cemetery in West Barnet, VT. For more information or to share memories and condolences go to www.RossFuneral.com.