De Montebello, a junior at UMass Amherst, was arrested once in 2023 and twice in 2024 for protesting and vandalism related to Gaza, documents in Eastern Hampshire District Court show. On Oct. 25, 2023, de Montebello was one of 57 students arrested and charged with trespassing after a sit-in rally at the Whitmore Administration Building. Later, de Montebello was one of the 130 students arrested at UMass Amherst on May 7, 2024, for rioting, failure to disperse and disorderly conduct, court documents show. Later that year, de Montebello was arrested on Oct. 30 and charged with four counts of vandalizing property. He was allegedly caught on camera with another UMass Amherst student, using graffiti to display messages related to the war in Gaza, according to the statement of facts associated to this case.