Great Baseball Nicknames: ‘Penitentiary Face’ / ‘Hac Man’- Jeffrey Leonard. Jeffrey Leonard played 14 seasons in the major leagues- for 5 teams but I always think of him with the San Francisco Giants in the late 80’s and especially for the highlight of his career- when he won the MVP for the NLCS in 1987. . Leonard got the nicknames ‘Penitentiary Face’ -due to his hard looks. He got the nicknames ‘HacMan’ -because of his tendency to go up the the plate swinging at pitches. He had another nicknames ‘One Flap Down’- when he hit a home run he would run around the bases with one of his arms pinned to his body. Leonard after his baseball career- managed some in the minor leagues. I know a fellow who played for Leonard in the minors. Leonard had a bad reputation as a ballplayer- for being moody. I had to ask this guy what it was like to play for Leonard. He was very diplomatic. He said Leonard wasn’t a great communicator- the manager’s door would often be closed. But Leonard was OK to play for. I didn’t press him for details. I sensed he didn’t want to really tell what it really was like.