Calafiore entered the Big Brother house on Day 1 with the first group of contestants. On Day 2 he formed an alliance with Derrick Levasseur called "The Hitmen". Throughout the season, the two secretly worked together with the ultimate goal of being the final 2 players left in the game on finale night. Calafiore initially won the Head of Household in Week 2, but his victory was rescinded after producers saw him touch the ground before he hit the buzzer. In week 4, Calafiore won HOH alongside Frankie Grande and nominated Victoria Rafaeli and Brittany Martinez for eviction. Calafiore's nominees lost the Battle OfThe Block competition, therefore, Calafiore remained HOH and Grande was dethroned. In Week 8, Calafiore was nominated for eviction alongside Caleb Reynolds by HOH Grande. Calafiore and Reynolds lost the BOTB competition and remained on the block as a result. Calafiore was then nominated aside his former ally Zach Rance after Grande used the POV on Caleb and backdoored Rance. Calafiore survived eviction. In Week 9, he won his second HOH and became the first solo HOH of the season. He nominated Donny Thompson and Nicole Franzel for eviction. The same week, Calafiore won his first Power of Veto and chose to keep the nominations the same, which resulted in Thompson's eviction. In Week 11, Calafiore was nominated alongside Rafaeli by Grande who was the HOH. However, due to a twist that reset the game by one week, both Calafiore and Rafaeli got off the block. In Week 12, Calafiore won his second and third Powers of Veto of the season. On Day 90, he was the sole vote to evict Reynolds. On Day 97, he won the final HOH of the season. He evicted Rafaeli and took his ally Levasseur to the final 2. Calafiore became the runner-up of the season, losing to Levasseur on a 7-2 vote, winning $50,000. Calafiore's older brother Paulie was a contestant on Big Brother 18, where he placed eighth.
Career
Calafiore joined Keller Williams Realty, representing Shrewsbury, New Jersey, in October, 2019. In 2014 Calafiore appeared in an ad campaign for American underwear brand C-IN2 and was in several issues of Seventeen Magazine as part of their 2014 Hot Guys Panel. Prior to his television appearance, Calafiore spent two years as an event host at Total Entertainment in Hackensack, New Jersey. He was also a sales associate at ADP for six months in 2015. Following his appearance on Big Brother 16 Calafiore signed with New York-based modeling agency Soul Artist Management. He has since appeared in Winq Magazine, Men's Fitness, LOVE Magazine, Risbel Magazine, an ad campaign for Swissgear, and three editorials for The Fashionisto. Calafiore has appeared in fashion shows as a model for Malan Breton, Gents, and Ricardo Seco. In 2016 Calafiore co-starred in the independent film What Happened Last Night.