Cubs’ biggest moves at winter meetings, from Jon Lester to Mordecai Brown

The winter meetings are back in person this year for the first time since 2019. They begin Monday.

SHARE Cubs’ biggest moves at winter meetings, from Jon Lester to Mordecai Brown
Cubs pitcher Jon Lester reacts after retiring the side during the seventh inning against Cleveland Indians in Game 7 of the 2016 World Series. His signing in December 2014 goes down as perhaps the best in club history.

Cubs pitcher Jon Lester reacts after retiring the side during the seventh inning against Cleveland Indians in Game 7 of the 2016 World Series. His signing in December 2014 goes down as one of the best in club history.


The flurry of movement sparked by early roster deadlines has died down. The Cubs haven’t been part of the early trades or signings since. But have no fear, the winter meetings are right around the corner.

Each year, the winter meetings ignite activity. Having representatives from every team under one roof has a way of getting things done. And for the first time since 2019, the winter meetings are back in person, kicking off Monday.

The Cubs promised they’d be active this offseason, and they’ve made big moves before at this time of year.

Here’s a collection of the most significant moves — good, bad, recent and long ago — the Cubs have made during the winter meetings.

Signing Jon Lester

The Cubs’ best free-agent signing of all time came together during the 2014 winter meetings. The club agreed to terms with Jon Lester on a six-year, $155 million contract and made it official a few days later.

It’s easy to say in retrospect that Lester’s signing was what catapulted the Cubs into a run of five playoff appearances in six years, including three straight National League Championship Series and a World Series victory. But Kyle Hendricks, the last remaining Cub from that title team, said he felt at the time that Lester’s arrival was a turning point.

“When that happened in the offseason, now you knew,” Hendricks told the Sun-Times recent recently. “I hadn’t maybe thought about it, but I knew, OK, this is a team now that is all in. We’re going somewhere. We’re winning.”

Win they did. And Lester, posting a 3.64 ERA and .636 winning percentage during his time in Chicago, claimed two All-Star selections and came in as high as second in NL Cy Young voting as a Cub.

Trading for Mordecai Brown

From a recent winter meetings to an early iteration: The story of how Hall of Famer Mordecai Brown landed with the Cubs began as the National League met in December 1903. The Cubs were rumored to be trading right-hander Jack Taylor to Cincinnati, according to

Only half of that report in “The Sporting News” came to fruition. The Cubs sent Taylor and catcher Larry McLean to St. Louis for Brown and catcher Jack O’Neil. And thus, the pitcher nicknamed “Three Finger” began a nine-year run in Chicago.

Brown went to the World Series three straight years with the Cubs and won two of them.

Trading Lee Smith to Red Sox

The Cubs haven’t only struck up deals to trade for future Hall of Famers at the winter meetings. They’ve also sent them away. Cue 1987.

The Cubs traded Lee Smith to the Red Sox for pitchers Al Nipper and Calvin Schiraldi.

Smith, whom the Cubs drafted in 1975, already had been an All-Star twice. He’d go on to earn five more All-Star selections and win three Rolaids Relief Man Awards in his decorated career.

Nipper pitched in just 22 games for the Cubs. Schiraldi posted a 4.19 ERA in parts of two seasons with the team.

Signing Ben Zobrist

In Ben Zobrist, the Cubs got a utility player, a 2016 All-Star and a postseason hero. They secured the man who’d record the biggest hit in Cubs history.

Zobrist famously drove in the go-ahead run in the 10th inning of Game 7 of the World Series, hitting an opposite-field double in the Cubs’ curse-breaking victory. He was named MVP of the series.

Zobrist’s Cubs tenure began with a winter meetings signing in 2015. He inked a four-year, $56 million contract.

Trading Bruce Sutter to Cardinals

Hall of Famer Bruce Sutter’s career was largely split between the Cubs and the rival Cardinals. That switch between the teams was courtesy of a winter meetings trade in 1980: Sutter to St. Louis for outfielder Leon Durham, third baseman Ken Reitz and utility player Ty Waller (the player to be named later).

Sutter had won the NL Cy Young Award two seasons before and was on a four-year All-Star streak. But before trading Sutter, the Cubs tried to lowball him in arbitration.

They lost the case, and Sutter was awarded a $700,000 salary for what would end up being his last year with the Cubs, who had offered $350,000.

Durham was a two-time All-Star in his 7½ seasons with the Cubs. Reitz and Waller’s tenures were more brief. Sutter’s departure at least made room for Smith to take over as closer.

Sutter added two more All-Star selections to his résumé with the Cardinals.

Signing Ted Lilly

Lefty Ted Lilly was an All-Star, led the league in starts in 2008 and posted a 3.70 ERA in his time with the Cubs. But his 2006 signing also became part of Cubs winter meetings lore.

In 2006, general manager Jim Hendry was hospitalized for an angioplasty procedure. But he kept working.

“Jim was hooked up to an EKG machine, and we got it done,” Lilly’s agent, Larry O’Brien, told reporters at the time.

The result of Hendry’s efforts: Lilly signed a four-year contract for $40 million.

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