Caloiaro attended Archbishop Mitty High School in San Jose, California, where he led the team to the 2008 State Division II title game. He ranked second on the team in scoring and led the squad in rebounding. Caloiaro captured First Team honors from the san Jose mercury News and earned all-West catholic athletic League second team honors after senior season. Caloiaro played college basketball for the University of San Francisco's Dons, where he averaged 14 points, 5.9 rebounds, 2.3 assists and 1.7 steals per game as a senior. Caloiaro ranked fifth on USF career 3-pointer list with 131 and tied for third in the West Coast Conference with six double-double performances. On February 28, 2012, Caloiaro earned a spot in the First-team All-WCC.
Professional career
Rilski (2013)
On January 31, 2013, Caloiaro signed with the Bulgarian team Rilski Sportist for the rest of the season. On April 7, 2013, Caloiaro recorded a season-high 26 points, shooting 9-of-13 from the field, along with 12 rebounds in a 91–95 loss to Cherno More.
On June 14, 2013, Caloiaro signed with the German team Mitteldeutscher for the 2013–14 season. On December 28, 2013, Caloiaro recorded a season-high 25 points, shooting 9-of-11 from the field, along with six rebounds and two assists in an 83–77 win over Medi Bayreuth. On January 18, 2014, Caloiaro participated in the 2014 BBL All-Star Game. On February 5, 2014, Caloiaro was named MVP of the Month for games played in January. Caloiaro finished his first season in Germany as the 2014 BBL Regular Season fifth-leading rebounder with 6.8 per game and also averaged 12 points and 1.5 assists per game. On April 24, 2014, Caloiaro earned a spot in the All-BBL First Team.
On August 1, 2015, Caloiaro signed with the Spanish team Obradoiro CAB for the 2015–16 season. On March 6, 2016, Caloiaro recorded a season-high 23 points, shooting 9-of-13 from the field, along with six rebounds and two steals in an 81–64 win over Manresa.
On July 3, 2016, Caloiaro signed with the Turkish team Büyükçekmece for the 2016–17 season. On February 11, 2017, Caloiaro recorded a double-double with a season-high 23 points and 14 rebounds, shooting 8-of-15 from the field in 69–73 loss to Tofaş. Caloiaro helped Büyükçekmece reach the 2017 FIBA Europe Cup Round of 16, where they eventually lost to Enisey.
On July 5, 2017, Caloiaro signed a one-year deal with Banvit. On May 28, 2018, Caloiaro recorded a career-high 29 points, shooting 10-of-12 from the field, along with 5 rebounds, 5 assists and 3 steals in 81–86 playoff loss to Fenerbahçe. Caloiaro helped Banvit reach the 2018 Turkish League Semifinals, as well as reaching the 2018 FIBA Champions League Quarterfinals, where they eventually lost to Monaco. In 54 games played during the 2017–18 season, Caloiaro averaged 12.4 points, 5.7 rebounds, 1.8 assists and 1.2 steals per game, shooting 43.8 percent from 3-point range.
Maccabi Tel Aviv (2018–present)
On June 26, 2018, Caloiaro joined the Israeli team Maccabi Tel Aviv of the EuroLeague, signing a one-year deal. On January 24, 2019, Caloiaro recorded a double-double of 20 points and 11 rebounds, shooting 6-of-9 from the field in an 84-75 win over Panathinaikos. Two days later, Caloiaro was named EuroLeague Round 20 MVP. Caloiaro helped Maccabi win the Israeli League championship title. On June 30, 2019, Caloiaro signed a one-year contract extension with Maccabi.
Personal life
Both of Caloiaro's parents played college basketball, his brother Vinny played professional soccer and sister Joan played high-level college volleyball. Then there are cousins who played for the U.S.A. national teams in soccer and rugby and another, Kerri Walsh Jennings, who won three Olympic gold medals in beach volleyball.
