Ciraldo, who has finally left his role as an assistant coach at the Penrith Panthers to link up with Phil Gould and the Canterbury Bulldogs for his first head coaching role, was rocked early in his tenure by Jackson's call to retire.
Jackson had all but held the Bulldogs together in recent years, with the club a regular finisher at the bottom of the table.
Speaking on The Bye Round Podcast with James Graham, Ciraldo revealed Jackson told him he would retire on his first day at Belmore.
“He just said, ‘Ciro, I'm sorry to drop this on you on your first day but I'm not going to play next year — my body has had enough',” Ciraldo recalled.
“I was still a bit under the weather from celebrations the day before, and I was sitting there with the captain, and he was telling me that he didn't want to play.
“I was a little bit in shock and didn't know what to say.
“I sat there and talked to him for a bit, and it was clear he'd thought about it a lot. I said go away and sleep on it; come back to me in a few days when you've had time to digest it.
“And he came back again and said he was done.”
Ciraldo admitted he didn't know how to react to the news.
“I didn't know how to handle it,” Ciraldo said.
“There are no textbooks I've read that says how to handle when your captain wants to retire early.”
Jackson has taken a role to remain at the club in the coaching department, but Ciraldo said it wasn't a condition of his retirement.
“He did it without asking for a job on the staff or anything like that. He was happy to just walk away from the final year of his contract,” he said.
“That just shows the type of man he is — he's incredible.
“We're really grateful that he's on our staff now and still has a part to play in the Bulldogs."
Ciraldo's tenure in charge of the blue and white will commence with a Round 1 trip to the Northern Beaches where the club will take on the Manly Sea Eagles, who are also looking for a drastic turnaround under new coach Anthony Seibold.