But even the optimistic Schuerholz couldn't predict when he signed Maddux to a five-year, $28 million deal that the right-hander would win three Cy Young Awards, 194 games, lead Atlanta to 10 division titles, three National League pennants and the 1995 World Series championship.
And, of course, easily land in the Hall of Fame.
Nothing defines the Winter Meetings, which return to Nashville, Tenn., on Monday for the seventh time, more than those moves made by two of the most successful general managers in baseball history.
Might there be a deal or a signing this year that has similar impact when the game's movers and shakers gather at the Gaylord Opryland Resort?
"You never know," said Gillick, 78, who just retired as president of the Phillies. "Those kinds of deals usually happen suddenly. And they don't come along very often."
The 1990 Meetings were at the Hyatt Regency near Chicago. Gillick had traded Junior Felix and Luis Sojo to the Angels for Devon White, Willie Fraser and Marcus Moore earlier in the week.
"I was touching base with San Diego, where Joe McIlvaine had just gone over there as the GM from the Mets," recalled Gillick. "I said, 'Hey, Joe, I'm looking for a right-handed hitter. Any possibility you'll move Joe Carter?' He answered, 'Yes, would you trade Fred McGriff?' I said I'd think about it. So, I said, 'Would you move Roberto Alomar?' He said he would, asking, 'Would you consider trading Tony Fernandez?' I said, 'Yes, we would.'
"I told Joe I'd talk to my people and get back to him the next day. We decided this was a good fit for what we needed and made the deal."
Gillick -- who during 27 years as a general manager with the Blue Jays, Mariners, Orioles and Phillies had teams in the postseason 11 times -- believes no deal he made had as much impact.
"That really put us [Blue Jays] over the hump," said Gillick. "Nothing stands out as much."
Toronto received Alomar, who ultimately was elected to the Hall of Fame, and Carter, whose walk-off homer in Game 6 won the 1993 World Series over Philadelphia.
Gillick will be back at the Winter Meetings this year, "and no matter what happens, I'll be thinking back to that deal in 1990."
Maddux -- at 26, with a 20-11 record and a 2.18 ERA for the Cubs -- had won the 1992 NL Cy Young Award before becoming a free agent. He was close to signing with the Yankees after touring New York.
"When I called his agent, Scott Boras, Greg and his wife were on their way back to their home in Las Vegas from New York, where they'd gotten the red-carpet treatment," Schuerholz said. "When Greg found out we were interested, he told his agent to hold on. He told him the Braves are an organization 'I really like what they're doing and feel very good about the people there.' We got him!"
Schuerholz, now the Braves' president, won a record 14 consecutive division titles as GM.
"I've made a lot of transactions at Winter Meetings, trades at the Deadline -- you name it," he said. "But the most dramatic one and the one that stands out for me was the signing of Greg Maddux."
Sadly, at the 1992 Meetings in Louisville, Ky., on the same day (Dec. 9) that Schuerholz signed Maddux, Carl Barger, the Marlins' first president, died from a heart attack.
For five years after that, there were no Winter Meetings. Baseball officials had become disenchanted by the way the sessions were evolving. They did not resume until 1998 -- in Nashville.
MLB historian John Thorn believes the meetings date to 1857.
"That was the first time top-rank amateur clubs of New York and Brooklyn met in what was formalized the next years as the Convention of the National Association of Base Ball Players," Thorn said.
My first Winter Meetings was in 1958 in Washington. Over the years, there were three trips to Hawaii and other stops all over the country.
Once, during a 1975 session in Hollywood, Fla., the late Bill Veeck, who was running the White Sox for the second time, set up a table in the hotel lobby with a sign, "Ready to Deal!"
During that same week, at the Diplomat, it was the Yankees who made the headlines. First, they traded Doc Medich to the Pirates for Willie Randolph, Ken Brett and Dock Ellis. The Yanks followed that on the same day by sending Bobby Bonds to the Angels for Ed Figueroa and Mickey Rivers.
This one I'll never forget: In the mid-1970s, the Phillies' Paul Owens and the Tigers' Jim Campbell talked trade late into the night in their hotel suite. Campbell thought he had traded Bill Freehan to Philadelphia for Bob Boone. In fact, word had leaked to the media of the deal involving the two catchers.
Not so. Owens said before daybreak that there was no deal.
The next morning, Campbell and the Tigers held a news conference stating they thought they had made the trade, but it didn't happen. Campbell's comment was historic, if not priceless: "How do you unshake a handshake?"
"When you're at these Meetings, you're focused on not what the industry is doing or how exciting baseball transactions are," Schuerholz said. "You're focused on getting the job done for your organization.
"Somebody may sign a free agent or make an acquisition that alters the landscape a bit, which might make you adjust the timing or the level of your offer. Really, it's what you're doing for your team and that you leave there with a stronger team."
Schuerholz believes aside from the huge attention free agents and their agents demand, the biggest change in the Winter Meetings is the enormous media coverage.
And these media folks will be in full force in Nashville, hoping there'll be headlines like the ones Gillick and Schuerholz made decades ago.