"Personally, it was hard to see Emmitt in red"

This quote by Jerry Jones is describing the time when Emmitt Smith, a previous Dallas Cowboys running back, left the team to sign up with the Arizona Cardinals. Jones was the owner of the Cowboys at the time and was very close to Smith, so it was tough for him to see his good friend in a various group's uniform. Jones was likely feeling a mix of feelings, including sadness, dissatisfaction, and even a little anger. He was most likely sad to see Smith go, dissatisfied that he was unable to keep him on the group, and mad that Smith had chosen to leave. Jones was also likely feeling a sense of pride in Smith for achieving his dream of playing in the NFL, but it was still tough for him to see Smith in a various team's colors.