Rather than sit the rookie, Jackson decided to play Callaway for the majority of Thursday's preseason opener against the New York Giants.
"I was trying to make him play the whole game if we could. I did not want him to come out," Jackson said of Callaway, who failed to inform the Browns that he was cited for marijuana possession and a suspended license last week.
"That was part of the consequence of what he has been through, and he knows it. That is what it was. Either you sit him or make him play. I thought it was better to make him play.
"Make him play as long as he could. There were a couple of times he kept waving to come out, and we said, 'No, stay in.'"
Callaway was nursing a rib injury during practice on Sunday, with Jackson indicating that it was sustained in Thursday's game.
The 21-year-old Callaway had a turbulent career at Florida that caused him to tumble to the fourth round of the 2018 NFL Draft. His arrest came hours before Cleveland traded wide receiver Corey Coleman to the Buffalo Bills.
Last Monday, Callaway was elevated to the first-team unit in place of Coleman, the No. 15 overall pick of the Browns in the 2016 NFL Draft.
Callaway was suspended twice at Florida and missed the entire 2017 season for allegedly using stolen credit card information to fund bookstore accounts.
At the NFL Combine, Callaway tested positive for drugs, and in 2016 he was cleared of sexual assault allegations. Because of a diluted urine sample at the Combine, Callaway already is in at least Stage 1 of the NFL's Substance Abuse Program, Cleveland.com reported.
Despite his off-the-field troubles, Callaway did produce on the field. He recorded 89 receptions for 1,399 yards and seven touchdowns while starting 24 of 26 games for the Gators.
Also a weapon on special teams, Callaway returned six kickoffs for 176 yards and a score, while also returning 54 punts for 653 yards and a pair of touchdowns.