It might have been a year in the 1970s, when the Philadelphia Phillies made a blockbuster deal with the Detroit Tigers, then rescinded their offer.
"How do you unshake a handshake?" angry Tigers officials were asking the next morning.
Or 1992, when free-agent slugger Barry Bonds and his agents, who were working out a $43.7 million deal with San Francisco, turned the Louisville meetings into a circus.
Or the two long trips to Hawaii, when the sessions were held there.
Or 1978, when Pete Rose sneaked into an Orlando hotel to sign with the Phillies after free-agent negotiations had abruptly ended 10 days earlier and he walked away. I was lucky enough to break that story.
On second thought, my most memorable has to be 1981 in Hollywood, Fla.
I spent my honeymoon covering those meetings, a decision wife Patricia will never let me live down.
I don't remember what deals were made that week, but that should tell you how important baseball's December ritual is to somebody who's spent over 50 years reporting the sport.
Just ask Patricia B.
The meetings have dramatically changed since 1962, when they were held in Rochester, N.Y., but there will be just as much excitement, just as much anticipation when the sessions begin Monday in Las Vegas.
Will premier free-agent pitcher CC Sabathia accept the Yankees' reported $140 million offer? Will the Angels be able to keep All-Star first baseman Mark Teixeira?
What about Manny Ramirez, Ben Sheets, Oliver Perez or Andy Pettitte?
And how much will the economic meltdown everyday people are suffering through affect baseball?
The dynamics have changed, the talked-about dollars border on insanity, but the purpose of the Winter Meetings remains the same.
John Schuerholz, one of the most successful general managers in baseball history with the Atlanta Braves, has been going to the Winter Meetings since 1967. He says there's no better forum for a GM than these sessions.
"You can set up deals, prepare for deals, lay the groundwork for deals, have long conversations in our industry beforehand, but it always seems like it isn't until we get together eye-to-eye at the Winter Meetings deals finally get done," says Schuerholz, now Braves president. "All of the tap dancing is over."
He adds: "This is always a time for the reinforcement of the celebration of the connectivity between the Major Leagues and Minor Leagues. At the Winter Meetings, we're all thrust together in a positive way."
For Schuerholz, those 1992 meetings in Louisville are probably his most memorable.
"That was when I signed Greg Maddux," he says. "That was the biggest acquisition I was ever involved with at the meetings."
Maddux, a certain Hall of Famer, won 194 of his 355 victories with the Braves (1993-2003) and three of his four National League Cy Young Awards.
Schuerholz sadly remembers that is was at the 1992 Winter Meetings when Florida Marlins president Carl Barger died suddenly. It was also after those meetings then interim Commissioner Bud Selig ordered a hiatus to the Winter Meetings because he reasoned they had gotten out of hand mostly because they were dominated by agents.
Ask Schueholz, whose Braves teams won a record 14 consecutive division titles, if the meetings are fun and there's hesitation.
"I wouldn't call it fun," he says. "It's an exhilarating time. In my later years, the meetings became more challenging with the expectations of the media. Thankfully, our game is covered in more depth than it ever has. It started to turn, though, when agents began to carve out more of the general managers' time. Less time was spent on tending to the needs of baseball because of that."
Pat Gillick, who's just retired after guiding the Phillies to the World Series championship, looks back to the 1990 Winter Meetings as the most significant during his storied career.
Gillick, then the Toronto Blue Jays GM, dealt Fred McGriff and Tony Fernandez to the San Diego Padres for Joe Carter and Roberto Alomar.
"If you look back, that was the deal that led to our two World Series championships in the 1992 and 1993," says Gillick, "I enjoy the meetings because you get an opportunity to see a lot of people you don't normally see over the years. From the standpoint of the meetings you have, it can become pretty grueling. It's a grind."
Yankees GM Brian Cashman plans to closet himself in his Bellagio suite as he attempts to make major moves to strengthen the team's pitching, al la sign Sabathia, et al.
"My memories of Winter Meetings are mostly about what other people do," says Cashman. "I remember when Alex Rodriguez signed that [10-year, $252 million] contact with the Texas Rangers, the buzz it created."
Cashman agrees he's been deeply involved at the Winter Meetings, "but as a kid growing up I remember how excited I was reading about the rumors, the trades, the possibilities of this and that.
"But as a participant, I always get disappointed. You feel like you get close to something that could really help you and then it goes up in smoke."
Murray Chass, a Hall of Fame baseball writer with The New York Times before retiring earlier this year, marvels at the number of players' names and rumors that circulate during the meetings.
"I always caution fans that most everything they hear seldom comes true," he says with a chuckle.
And sometimes a deal that appears done really isn't.
Like in 1974, in New Orleans, when Phillies GM Paul Owens traded Bob Boone, Larry Christenson and a couple of prospects to the Tigers for Bill Freehan, Jim Northrup and two Minor Leaguers.
Late into the night, Owens called Tigers GM Jim Campbell and pulled the plug on the deal. The next morning the Tigers held a press conference and asked the famous rhetorical question: "How do the Phillies unshake a handshake?" as he criticized them.
So, another Winter Meetings chapter is about to be written.
And regardless, this is certain: Covering this ritual is no honeymoon.
Hal Bodley is the senior correspondent for MLB.com. This story was not subject to the approval of Major League Baseball or its clubs.