One of the early topics focused upon was Thome's 500th career homer, hit in walk-off fashion at U.S. Cellular Field against the Angels' Dustin Moseley on Sept. 16, 2007. Thome had connected on No. 499 on Sept. 12, but had gone hitless in the next two games.
Andrea, Thome's wife, was pregnant with their second child and wasn't going to be able to go on the next road trip to Kansas City and Minnesota.
"Before that Sunday game, she said, 'Will you please just hit one?" said Thome, drawing laughs from the packed Red Lacquer Room of the Palmer House Hilton.
As Thome's family raced onto the field to celebrate his game-ending blast, Baines picked up Thome's bat and later gave it to his father. That baseball resides at the National Baseball Hall of Fame, taken there by Thome and his father, but Thome has No. 600 at his home. That connection came against left-handed reliever Daniel Schlereth on Aug. 15, 2011, the second of a two-homer game.
Jackson was amazed by the accomplishment of Thome's 612 career homers. He was more amazed by Thome remembering Schlereth's name.
"I don't remember anybody's name," a smiling Jackson said.
Other areas of conversation ranged from toughest and easiest pitchers to face, to Jackson hitting a leadoff homer in the 1989 All-Star Game off of Rick Reuschel, to Baines comparing the 1983 White Sox to the 2005 White Sox.
"Both teams had the type of players who wanted to win," Baines said. "It didn't matter if we were four or five runs back."
Later in the session, a fan asked Thome and Jackson to provide Spring Training advice to young White Sox players. That inquiry led to this humorous exchange concerning their upcoming trips to Glendale, Ariz.
"I thought I was going to play golf," Jackson said.
"I'll play golf with you," Thome said. "But I have to go to the ballpark."
"We are ambassadors," said Jackson, who recently rejoined the White Sox as a team ambassador. "We should have diplomatic immunity."
When a question of how to handle failure and slumps came up, Jackson handled the topic through a story from a red-hot day at Kauffman Stadium. It was somewhere around 123 degrees on the turf, Jackson said, he had gone 0-for-3 and was sitting in the dugout steaming both literally and figuratively.
As Jackson had his feet in ice water, one of his teammates told him to chill out by getting a cold drink and get back after it at the plate. So that's what Jackson did, going to the clubhouse and grabbing a Bud Light.
Jackson hit one of his 141 career home runs in his next at-bat.
Just another part of history shared on Sunday, as Bo clearly knows entertainment.