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South Side Sox Top Prospect No. 40: Benyamín Bailey

He’s taken quite a tumble from the high end of this list, but this strapping outfielder is poised for a comeback.

It was a rough 2021 for Benyamín Bailey, but he’s young enough that a big rebound is possible.
Tiffany Wintz/South Side Sox

Benyamín Bailey

Left Fielder
6´4´´
215 pounds
Age: 20
2020 SSHP Top Prospect Ranking: 26
2021 SSS Top Prospect Ranking: 12
SSS rank among all left fielders in the system: 3

Benyamín Bailey, a native of Panama, received a minimal $35,000 signing bonus from the White Sox on April 27, 2019, with literally no fanfare. However, by the time he ended his first pro season five months later, Bailey was the best-known prospect on the DSL roster and considered a rising star. In 55 games totaling 185 at-bats, Bailey slashed an incredible .324/.477/.454 with 12 doubles, three triples, two homers, 19 RBIs, 52 walks (21.4%), 40 strikeouts (16.5%), 10 stolen bases and 166 wRC+. Bailey’s OBP was hovering around .500 for most of the year, before a late-season slump dropped him to .477. With that said, Bailey still led the league in that department and was near the top in walks and OPS as well.

In most cases, the DSL leaders are either returning players and/or are much older than the league average; in Bailey’s case, this was his first year in professional ball and he was about six months younger than his competition. As a result of his debut, Bailey moved up to 19th in the team’s 2020 prospect rankings.

Nearly everything that went right for Bailey in 2019 went wrong for him in 2021. In part due to the 2020 season lost to the pandemic, the slugger was given an aggressive assignment, to Low-A Kannapolis, where he floundered; unfortunately, he did no better after a demotion to Arizona, making 2021 a truly lost season. In a combined 61 games totaling 202 at-bats, Bailey slashed just .193/.303/.272 with two doubles, one triple, four homers, three stolen bases, 31 walks (16.0%), 71 strikeouts (30.7%) and 87 wRC+. Bailey still walked at a tremendous clip, but fanned much more frequently while producing a far lower average. While the competition was a bit more difficult, the likely contributors to his down season were the long layoff and adjusting to a new culture.

When MLB Pipeline ranked Bailey among the organization’s Top 20 prospects in 2020, they gave him the following grades: 50 for hitting, power and fielding; 45 for running and arm. With his large frame, one would expect more than six homers in 116 career games. He hasn’t taken advantage of his raw power yet, as he has hits grounders at a 53% clip when he does make contact. Hopefully with experience, Bailey can add some loft to his swing and lay off low offerings. He does run well for his size, but is expected to slow down as he gets older. Bailey’s arm is considered fringy at best, so even though he’s split time between left and right field, he’s better suited in left.

No longer ranked among the system’s Top 30, Bailey can easily return to that list with a productive 2022. It wouldn’t be surprising to see him begin next season with an extended spring training stay in Arizona, and move up to Kannapolis once a Cannon Baller is promoted to Winston-Salem.


2022 South Side Sox Top 100 White Sox Prospects

40. Benyamín Bailey, LF
41. Tyler Johnson, RHRP
42. Andrew Perez, LHRP
43. Tyler Neslony, LF
44. Theo Denlinger, RHRP
45. Hunter Schryver, LHRP
46. Jefferson Mendoza, C
47. Harvin Mendoza, 1B
48. Gil Luna Jr. LHRP
49. John Parke, LHSP
50. Victor Quezada, 3B
51. Haylen Green, LHRP
52. Sammy Peralta, LHRP
53. Yoelvin Silven, RHRP
54. Taylor Broadway, RHRP
55. Noah Owen, RHRP
56. Luis Curbelo, 3B
57. Bryce Bush, RF
58. James Beard, CF
59. Xavier Fernández, C
60. Wilber Sánchez, SS
61. Kohl Simas, RHRP
62. Johan Dominguez, RHSP
63. Jagger Rusconi, 2B
64. Ronaldo Guzman, LHSP
65. Laz Rivera, 3B
66. Adam Hackenberg, C
67. Will Kincanon, RHRP
68. Lane Ramsey, RHRP
69. Tommy Sommer, LHSP
70. Randel Mondesi, RF
71. Shawn Goosenberg, 2B
72. Zack Muckenhirn, LHRP
73. Cameron Butler, CF
74. Godwin Bennett, RF
75. Logan Glass, CF
76. Dario Borrero, 1B
77. Craig Dedelow, RF
78. Carlos Hinestroza, RHRP
79. Gunnar Troutwine, C
80. Kade Mechals, RHSP
81: Caberea Weaver, CF
82. Layant Tapia, SS
83. Homer Cruz, RHRP
84. Kaleb Roper, RHSP
85. Jerry Burke, RHSP
86. Emerson Talavera, RHRP
87. Isaiah Carranza, RHSP
88. Davis Martin, RHSP
89. Tyler Osik, 1B
90. Samil Polanco, 3B
91. Manuel Veloz, RHRP
92. Pauly Milto, RHRP
93. Fraser Ellard, LHRP
94. Colby Smelley, C
95. Manuel Guariman, C
96. Everhett Hazelwood, RHRP
97. Garrett Schoenle, LHRP
98. Kyle Kubat, LHRP
99. Anderson Comas, RF
100. Jake Elliott, RHRP