Longhi was originally selected by the Boston Red Sox in the 30th round of the 2013 MLB Draft out of Venice High School in Florida, where he helped the Venice Indians win the Florida 7A State Championship and finish No. 2 in the final national rankings in 2013. By the time Longhi was a senior at Venice, joined the Rawlingsfirst team All-American and played in almost every major tournament for Perfect Game. Longhi came to terms on a contract calling for a reported over-slot bonus of $450,000, the fourth-highest bonus handed out by the Sox, with the organization buying him out of a commitment to Louisiana State University. Longhi was rated by Baseball America at No. 8 as one of the best pure hitters in the 2013 high school draft class. He is a rare right-handed hitting, left handed throwing outfielder who possesses a strong arm, delivering fastballs when he was a two-way player in high school. Versatile enough to also play at first base, he is also a solid-average defender with strong instincts, soft hands and good footwork. Longhi debuted with the GCL Red Sox late in 2013, playing for them 16 games before joining the Lowell Spinners in 2014. He then gained a promotion to the Greenville Drive in 2015. In 2015 Longhi played mostly right field for a Drive squad, and he showed adequate actions and plenty of arm in the field. Longhi looked to be in noticeably better shape than past seasons, looking stronger, quicker, and more agile in the field and on the basepaths. He appeared more mature, even though he was young for his 2013 draft class and turned 20 years old in August. As a result, his.281/.338/.403 line with seven home runs, 22 doubles, three triples and 62 RBI was significant, because he was facing pitchers two or more years older than him who could throw regularly and get up to. Longhi opened 2016 with High-A Salem Red Sox, appearing at first base in 99 games and in right field in 25 games, though in some games he appeared at both positions. He slashed.282/.349/.343 in 471 at bats and led Salem with 77 RBIs and 40 doubles while collecting a second-best 133 hits behind Rafael Devers, as his 40 doubles were second-best in the Carolina League and his RBI totals ranked him fifth. Longhi topped the Red Soxminor league system in RBIs and doubles, was fifth in hits, and tied for third in games played. Longhi began 2017 with the Double-A Portland Sea Dogs. He was traded to the Cincinnati Reds for international signing bonus pool space on July 2. Cincinnati assigned him to the Double-A Pensacola Blue Wahoos and he finished the season there. In 69 total games between the two teams, he batted.266 with seven home runs and 40 RBIs. He became a free agent following the 2019 season. On December 20, 2019, the Boston Red Sox signed Longhi to a minor league deal and invited him to spring training.
