On June 19, 2016, during a season when Callaway would play an important role in helping the Indians reach the World Series, the woman who went on road trips with Callaway received a text message that included a shirtless photo from Callaway taken inside a clubhouse. He was wearing an Indians cap.
“What are you doing right now? Let me see u. I am headed out soon for (a) game,” part of the text message read.
In late 2016 or early 2017, he sent an unsolicited full-frontal nude picture of himself in a locker room to the friend of another woman he was involved with sexually, according to someone who saw the photo and asked about it. The friend worked in the Indians organization at the time.
As The Athletic previously reported, Callaway also sent a former Indians employee suggestive messages on LinkedIn in late December 2015. He also had made a pass at her on the field during the season.
None of the women who interacted with Callaway during his time in Cleveland reported these interactions through any official channels.