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A native of Cohasset, Massachusetts, Monaco was a three-sport athlete at Cohasset High School. He attended the University of Notre Dame and wrote for the school's student newspaper with the intent to become a Major League Baseball general manager, similar to the path former Red Sox general manager Theo Epstein had when he attended Yale. Monaco eventually transitioned to the school radio station at Notre Dame and subsequently began his broadcasting career.
Monaco interned at NESN in 2012 while at Notre Dame, before broadcasting Fighting Irish sporting events. In 2013 and 2014, he called games for the Wareham Gatemen of the Cape Cod Baseball League. He also called Western Michigan Broncos basketball games while at Notre Dame before interning with the Red Sox's Triple-A affiliate Pawtucket Red Sox as a radio broadcaster in 2017.