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Once Buffalo quarterback Tyree Jackson and receiver Anthony Johnson left for the NFL after the 2018 season, the transfer floodgates opened. Osborn was one of several former Bulls players that found new homes for 2019, picking Miami. He started all 13 games as a senior, leading the team in receiving (50-547-10.9, five TDs) and contributing as a returner (16-255-15.9 punts, 10-201-20.1 kickoffs). He graduated from Florida's IMG Academy after spending three years at Lincoln High School in Ypsilanti, Michigan, where he starred in football and excelled in sprint events for the track team as a junior. As a redshirt freshman, Osborn started two of 12 games played for the Bulls (8-105-13.1, one TD). He was a bigger part of the offense his sophomore season, starting seven of 12 games (35-493-14.1, four TDs) while also handling kickoff (16-310-19.4) and punt (8-82-10.3) return duties. He and Johnson made a dynamic receiver duo in 2018, garnering second-team All-MAC honors with 53 catches for 892 yards (16.8 per) and seven scores while continuing to contribute as a returner (7-135-19.3 kickoffs, 25-257-10.3 punts).