Let’s look back at some of the biggest Winter Meetings moves in Cubs history. While this is hardly the definitive list of such transactions, here are five of the most notable Meetings maneuverings by Chicago over the years.

1. Lester chooses Cubs, changes culture
The Cubs were a young, up-and-coming, prospect-laden club that appeared poised to move out of a rebuild after the 2014 season. That process was accelerated at the '14 Winter Meetings in San Diego, where the North Siders "won the baseball lottery," as former Cubs manager Joe Maddon told reporters at the time.

The winning numbers were six years and $155 million, and veteran lefty Jon Lester was the recipient via the biggest free-agent contract for a pitcher in Cubs history. Just like that, there was a true and immediate expectation of not only winning, but contending for a World Series.

"We were investing in Jon Lester the person every bit as much as we were investing in Jon Lester the pitcher," former Cubs president of baseball operations Theo Epstein said. "And he came through in both areas for us in typical Jon Lester fashion."

In Lester's six years in Chicago, the club went to the playoffs five times, won three division crowns, reached at least the National League Championship Series three times and won the 2016 World Series. The lefty was the NL Cy Young runner-up in '16 and the co-MVP of the that year's NLCS.

Lester topped 1,000 career innings with the Cubs in 2020, going 77-44 with a 3.64 ERA in 171 games with the team. That does not include the 2.44 ERA that he spun in 70 postseason innings for the franchise.

"Huge tip of the cap to him," Epstein said. "He's made a huge impact on Chicago Cubs baseball."

2. Landing a World Series hero
The Cubs stormed through October in 2015, taking down the Pirates in the NL Wild Card Game and the rival Cardinals in the NL Division Series. When the Mets halted Chicago's march to the Fall Classic, the Cubs tackled the next offseason aggressively.

On Dec. 8, 2015, the Cubs signed super utility man Ben Zobrist, who had played for Maddon previously in Tampa Bay and was coming off a World Series triumph with the Royals. Chicago signed the versatile Zobrist to a four-year, $56 million deal that wound up being worth every penny.

"Look at what Zobrist did in the postseason," Epstein told reporters after the signing was announced at the Meetings in Nashville. "Facing the best pitching in the world, in the most competitive environment, he worked really good at-bats, put the ball in play when it needed to be put in play, drove the ball when it needed to be driven and found his way on base a lot.

"Those kind of winning, competitive at-bats are what we’re looking for -- it sets a great example for the young hitters that we have."

Flash forward to the 10th inning of Game 7 of the 2016 World Series in Cleveland. It was Zobrist who slashed the decisive, go-ahead double that put the Cubs on their way to ending their 108-year title drought. Zobrist took home World Series MVP honors for his heroics.

On the same day that Zobrist was signed, the Cubs swung a trade that sent Starlin Castro to the Yankees. That was the same offseason that brought Jason Heyward, John Lackey and Dexter Fowler into the fold for the '16 team.

3. Green ignites rebuild in '81
"I went to Chicago with guns blazing and big mouth blazing about what I intended to do."

The late Dallas Green gave those comments to Carrie Muskat in her book, "Banks to Sandberg to Grace: Five Decades of Love and Frustration with the Chicago Cubs." Green was hired as the Cubs' general manager prior to the 1982 season and he wasted no time in getting to work.

Green punched the gas on his rebuilding project at the 1981 Winter Meetings in Hollywood, Fla., where a major signing and trade came together on Dec. 8. The Cubs re-signed veteran righty (and franchise icon) Fergie Jenkins and also swung a four-player trade with the Phillies that brought Keith Moreland to Chicago.

That was a big day that foreshadowed what was to come. In January of 1982, Green swung another trade with Philadelphia that landed Larry Bowa and a prospect named Ryne Sandberg. At the '83 Meetings, Green oversaw a three-team trade that netted pitcher Scott Sanderson.

There were other moves along the way that helped turn the 38-65 Cubs of 1981 into a 96-win team that reached the NLCS by '84.

4. Dealing closers in Dallas
For this spot on the list, we're going to combine two Winter Meetings moves by the Cubs. They happened seven years apart nearly to the day, and both took place in Dallas. And both moves involved a future Hall of Fame closer leaving town.

On Dec. 9, 1980, the Cubs shipped Bruce Sutter to St. Louis in exchange for Leon Durham, Ken Reitz and Ty Waller. Sutter turned in a 2.39 ERA across the '76-80 seasons, averaging nearly 100 innings per year and picking up the NL Cy Young Award in '79. Alas, a contract dispute paved the way for an eventual trade.

Durham spent parts of eight years with the Cubs, hitting 138 homers, posting an .846 OPS, making two All-Star teams and playing a key role for the '84 division champs.

Sutter's exit allowed Lee Smith to assume the closing job for the Cubs, who saw him amass 180 saves with a 2.92 ERA from 1980-87. On Dec. 8, 1987, Chicago shipped him to Boston for a pair of pitchers. Neither lasted more than parts of two years with the Cubs.

After the trade, legendary Chicago Tribune writer Jerome Holtzman wrote that Smith "had begun to show irrefutable indications of wear and tear." As it turned out, Smith chalked up nearly 300 more saves over the next nine years, ending his career with 478 in total (an MLB record at the time).

5. Hendry signs Lilly from hospital
There are other Winter Meetings transactions from Cubs history that would also be worthy of inclusion in these rankings. To round out this particular collection, however, let's turn to one that was more about the tale than any statistics that followed.

At the Winter Meetings in Orlando in 2006, former Cubs vice president and GM Jim Hendry was not feeling well behind the scenes. At the same time, the agent for free-agent lefty Ted Lilly was busy trying to get a deal done for his client. A decision was going to be made at the Meetings, and the Cubs were up against the Yankees and Giants.

By the third day at the Meetings, Hendry was ill enough to be visited by a doctor, who suggested that the Cubs' head decision maker head to the hospital. New Cubs manager Lou Piniella did the driving and Hendry wound up on a path to a heart procedure that evening.

While in the hospital undergoing an EKG, Lilly's agent rang Hendry's phone and agreed to sign a four-year, $40 million pact with the Cubs. He was unaware that Hendry was in the hospital at that moment. Hendry had his angioplasty that night and the deal was finalized in the morning.