2025 South Side Sox Top Prospect No. 81: Caleb Freeman
Once the system’s top relief arm, his full season at Double-A has put him back on the right track
Caleb Freeman
Right-Handed Relief Pitcher
6´1´´
195 pounds
Age: 27
2020 South Side Hit Pen Top Prospect Ranking: 50
2021 South Side Sox Top Prospect Ranking: 32
2022 South Side Sox Top Prospect Ranking 18
2023 South Side Sox Top Prospect Ranking 44
2024 South Side Sox Top Prospect Ranking 53
2024 High Level Birmingham (AA)
Age relative to high level +1.5 years
SSS rank among all right-handed relief pitchers in the system 13
Overall 2024 season stats 2-5 ⚾️ 39 games (14 finished) ⚾️ 4 SV ⚾️ 43 2⁄3 IP ⚾️ 4.33 ERA ⚾️ 1.351 WHIP ⚾️ 56 K ⚾️ 26 BB
Caleb Freeman struggled with his control in college, and that problem has flared up some as a pro. However, he was healthy in college — and injury woes have plagued him since he has been in the White Sox system.
Right after being drafted, Freeman went right to work, doing well at all three of his stops (AZL, Great Falls and Kannapolis): In a combined 17 games totaling 24 2⁄3 innings, he saved four with a 2.19 ERA and 0.97 WHIP. In those innings, Freeman allowed just 15 hits (.170 OBA) and nine walks (8.9%) while striking out a whopping 38 batters (37.6%). It’s like he found his control and command overnight.
After the pandemic cancellation of the 2020 season, Freeman had grown in stature to such a point that then-farm director Chris Getz was tabbing the righty as the system’s reliever to watch in 2021. By all accounts, Freeman fulfilled his promise. In 25 appearances for Winston-Salem Freeman posted a 3.62 ERA and 1.32 WHIP, and in 14 games totaling 16 2⁄3 innings after promotion to Birmingam, he produced a 2.70 ERA and 1.20 WHIP.
In 2022, just as Freeman (buoyed by a select to the AFL after the 2021, to boot) could afford to make tentative plans for the South Side later in the summer, everything fell apart. Or, more likely, there were injury issues from the jump, as the ascendant righty walked six of 13 batters to open the season and saw little consistent use, a telltale sign of trouble. FanGraphs reported his velocity as being down several ticks by the time Freeman was rehabbing in the ACL at summer’s end.
The 2023 season brought a return to relative health for Freeman, as he shaved his months missed down from three in 2022 to two. His work in Birmingham to start the season, pre-injury, was solid (1.96 ERA) but post-rehab in the ACL, Triple-A treated him Freeman in a ghastly manner (6.08 ERA in 12 games and a WHIP more than 2). And at each level, Freeman failed to shake the wildness that made him risky even as a 15th-rounder, way back when.
With his career potentially in the balance, Freeman came through. He took a step down (of sorts) to Birmingham and played all year there. He was healthy and strong, filling a closer role and falling just one out shy of the biggest workload he’d ever taken on in the pros.
Freeman’s Baseball Cube player ratings
Durability 78 (unchanged from last season)
Strikeouts 66 (+3)
vs. Power 59 (+4)
Hittable 59 (+4)
K/BB 37 (+2)
Walks 27 (+1)
Average 54.33 (+2.33)
Freeman may no longer wear the gown as the “reliever to watch” in the White Sox system, but he added a key piece to his puzzle with a strong, full season in Birmingham (Freeman helped pitch the Barons to the Southern League title, including a scoreless outing in the championship clincher). Presume he sees Charlotte — and given his age, experience, and re-re-rediscovered command, the South Side is not out of the question.
2025 South Side Sox Top 100 White Sox Prospects
100. Cole McConnell, CF
99. Drake Logan, LF
98. Marcelo Alcala, RF
97. Lyle Miller-Green, 1B
96. Jared Kelley, RHRP
95. Adrian Gil, 1B
94. Adam Hackenberg, C
93. Loidel Chapelli, 2B
92. Eddie Park, CF
91. Chase Plymell, RHRP
90. Anthony Hoopii-Tuionetoa, RHRP
89. Tristan Stivors, RHRP
88. Pierce George, RHRP
87. Wes Kath, 3B
86. Daniel González, LHRP
85. Mikey Kane, 1B
84. Shane Murphy, LHSP
83. Connor McCullough, RHSP
82. Braden Shewmake, SS
81. Caleb Freeman, RHRP