The Indians' fan services department reportedly fielded repeated calls from an angry husband complaining that Callaway sent "pornographic material" to his wife in 2017.
These calls were brought to the attention of Indians president of baseball operations Chris Antonetti, general manager Mike Chernoff, and manager Terry Francona, sources told Ghiroli and Strang.
In February, Antonetti asserted that the Indians were unaware of Callaway's behavior, said there had never been any complaints against Callaway during his tenure with Cleveland, and described feeling "distraught" and "disturbed" after learning of the alleged behavior.
Antonetti's response didn't sit well with multiple people who interacted with Callaway while he worked for the Indians, prompting them to contact The Athletic.
"(Those) comments hit me the wrong way," one former team employee said. "I know that's the way Chris has to do it and run things, but the amount of people in that organization who know about all that stuff, I don't know how he can then face his staff."
In the last month, 12 current and former Indians employees told Ghiroli and Strang that "Callaway's sexual indiscretions permeated the workplace to such an extent that it would have been difficult for top officials to not be aware of his behavior, and they push back against any assertion that Callaway's actions ... caught team executives or MLB by surprise."
The Indians reportedly tried to smooth things over with the upset husband, who later emailed Major League Baseball about Callaway. The same person emailed the New York Mets in 2018, months after they hired Callaway as manager.
“I would like to think that if the Mets were aware of this situation, they would not want this type of person as their employee representing their organization," the email read.
The Indians released a statement in response to the latest report on Tuesday afternoon.
"Our organization continues to actively cooperate with MLB on their investigation into Mickey Callaway. It is important we honor the confidentiality and integrity of that investigation," the statement said, according to Mandy Bell of MLB.com. "While we don't believe the reporting to date reflects who we are as an organization, we will not comment further on the specifics of this matter."
On Feb. 1, Ghiroli and Strang reported that five women working in sports media said Callaway had behaved inappropriately toward them dating back to his time as Indians pitching coach and New York Mets manager.
Since then, more women have said that Callaway "made them uncomfortable by sending them inappropriate messages and/or photos, making unwanted advances and more while they worked for the Indians," according to Ghiroli and Strang.
Callaway, who was hired by the Los Angeles Angels to be Joe Maddon's pitching coach last October, was suspended by the team after the initial report in February.
In an email to The Athletic on Monday, Callaway wrote: "While much of the reporting around my behavior has been inaccurate, the truth is that on multiple occasions I have been unfaithful to my wife, and for that, I am deeply sorry. What I have never done is use my position to harass or pressure a woman. I am confident that I have never engaged in anything that was non-consensual."