In recent months and years, ESPN has become known for having hot take commentators and focusing more on being controversial and argumentative rather than analytical in their approach to sports. One need only see that their highest-paid personality, Steven A. Smith, has openly pondered a run for the office of President of the United States to see how different the network is than when it first began.
That being said, there are still a plethora of talented journalists, reporters, and other creators that work for ESPN. Many of them can be found assigned to the markets of teams they are assigned to cover. One of these is Jesse Rogers, who covers the Chicago baseball teams.
ESPN baseball insider Jesse Rogers got to sit in on the Chicago White Sox draft process

Last weekend and into this week, the 2026 Major League Baseball amateur draft took place. With the first overall pick, the Chicago White Sox selected UCLA shortstop Roch Cholowsky.
Many times in sports, analysts and fans have a pretty good idea of who the number one pick will be in any given draft. That was not the case in this year’s MLB draft, though. Chicago did not even know themselves what player they were going to take up until moments before the decision was made.
In what is an extremely rare piece, Rogers details the conversation had by members of the White Sox front office leading up to Cholowsky’s selection. He was able to document these because they invited him into their war room as they met to decide who to take with the first overall pick.
This excerpt from what is a much longer discussion is a great example of the kind of insight Rogers helped bring to fans:
Getz:“We’re down to these two guys. Is there anything we’re missing? Anything we haven’t talked about? Does anyone want to add anything?
A pause in the room opened the door for special assistant Dave Keller, who was instrumental in the team’s offseason acquisition of Japanese star Munetaka Murakami.
Keller:“In this position, it almost becomes like risk evaluation. So, what’s going to get Roch if something gets him? What’s going to trip up Grady? If something gets him.
“That’s the only thing that I would add, is which one feels like more risk than the other?”
The GM responded by referencing the question marks surrounding Murakami before he arrived in Chicago. He noted how the team helped “unlock” some things in Murakami and reaffirmed Getz’s belief that it’s up to the team to bring out the best in whoever it takes.
In an era where so much of what people think is influenced by movies, dramatizations, or other forms of media that embellish or even make up aspects of life in professional sports, it was very interesting to get a look at what really goes on behind those closed doors.