He played college football at Western Michigan and was signed by the Chiefs as an undrafted free agent in 2022.

He was an all-conference scholar athlete and was named Greater Metro Conference Offensive Lineman of the Year.

[1] Caliendo committed to Western Michigan University (WMU) but did not see any playing time as a true freshman in 2016.

He appeared on 967 total snaps and played a part in WMU ranking top three in the MAC for offensive yards per game with 445.7 (2nd), third down conversion percentage with .453 (2nd), fewest lost fumbles with 6 (2nd), fewest total turnovers with 14 (2nd), and most points per game with 33.1 (3rd).

The WMU offense ranked third in the MAC and placed 18th in the country for fewest allowed sacks per game with 1.38.

He did not allow any sacks in the season and helped the team rank top ten in the nation for points per game.

[1] Caliendo turned down a chance in the NFL and medical school to return to the WMU football team in 2021.

[3] After going unselected in the 2022 NFL draft, Caliendo was signed by the Kansas City Chiefs as an undrafted free agent.