When the Chicago White Sox selected right-handed pitcher Caleb Freeman with the 440th pick in the 2019 MLB draft, I’m not sure they had a ton of confidence that he’d eventually be pitching in the big leagues.
That's not a knock against Caleb either. It's just that players drafted in the 15th round are not usually blue-chip prospects that are fast-tracked to the Major Leagues.
On Sunday, news broke that the White Sox were shuffling around their major league roster, including optioning struggling reliever Penn Murfee to Charlotte, and recalling reliever Caleb Freeman to the majors for the first time in his career.
The promotion comes after 10.1 scoreless innings in Charlotte for Freeman in 2025 after he spent the entire 2024 season with Double-A Birmingham. Freeman, now 27, previously pitched for Charlotte during the end of the 2023 season, but had an inflated 6.08 ERA in 12 appearances. This time around, Charlotte has brought more success for Freeman, who will now get his first chance to prove he’s a major league reliever in a White Sox bullpen that is drowning.
The fact that the White Sox drafted Freeman in the 15th round and have turned him into a major league pitcher is a big win for the player development department, regardless of his production at the major league level from this day forward.
Caleb Freeman is in rare company
So how rare is it for a 15th round pick to actually make it to the big leagues? While it’s not completely unheard of, it’s certainly a notable feat.
Out of the 30 players drafted in 15th round of the 2019 MLB Draft, Freeman will be only the third to actually play Major League Baseball, and only the second to play for the team that drafted him.
The Twins selected RHP Louie Varland with the 449th pick, who has thrown 159 MLB innings, all with the Twins, and is currently on Minnesota's big league roster.
Infielder Brett Wiseley was drafted by the Rays with the 458th overall selection, and has played in parts of two seasons with the San Francisco Giants. Nobody else picked in that round in the 2019 draft has played in the Majors.
To put things in perspective, only four players from the 15th round of the 2018 draft ever played for a big league club and none of them are currently on MLB rosters. There are two players currently in Major League Baseball from the 15th round of the 2017 draft, but neither are with the team they were originally drafted by.
In summary, by getting drafted in the 15th round and making the majors with the team that drafted him, Caleb Freeman has done something that is exceedingly rare. The fact that he’s here at all is a big-time success by the White Sox player development staff - which has become a pitching factory of sorts in recent years.
15th rounders of MLB history
While making the major leagues from the 15th round is an accomplishment in itself, some may be wondering whether success is possible for a guy selected that late in the draft. The short answer is yes. Don't rule out the possibility that Freeman could be a legitimate piece for Chicago moving forward. We've seen it happen in the past.
Perhaps the most successful example of a 15th round draft pick happened in 1982, when the Oakland A’s selected high school OF Jose Canseco from the Miami area. Canseco, of course, went on to mash 462 major league homers over 17 seasons, and would likely be in Cooperstown if not for the allegations of using performance enhancing drugs.
On the pitching side, perhaps the most prominent example is an old friend. The San Diego Padres selected RHP Jake Peavy with the 479th pick in the 1999 MLB Draft out of high school in Mobile, Alabama. Peavy ended up a two-time all-star and finished with a 3.83 ERA over 15 Major League seasons. He appeared for the White Sox in five different seasons and pitched in 84 games with the Southsiders. Peavy won the NL Cy Young Award in 2007.
I am in no way saying that Caleb Freeman is going to have a Major League career at the level of Jake Peavy or Jose Canseco. The overwhelming likelihood is he does not. But allow Peavy and Canseco to be examples of successful careers stemming from the 15th round. The list of current major leaguers who were drafted in the 15th round includes Jack Suwinski, Tyler Wells, and Josh Winckowski. None of those players are superstars, but they’re serviceable big leaguers from late in the draft that provide value to an organization.
It remains to be seen the impact and production Caleb Freeman will have at the Major League level, but the fact that he’s here is a win for the White Sox and their player development department. This is the kind of thing that good organizations do.
The White Sox and their fans hope this will become a trend, and that we will see more late-round picks turn into major league players. If the White Sox can continue to find big league talent late in the draft, it’ll certainly be a large step toward perennial contention.