ORLANDO, Fla. — The Winter Meetings begin Monday at the Signia by Hilton hotel. Every general manager walking through those doors knows one thing for certain. When Brian Cashman and the New York Yankees show up, history tends to follow.
No franchise has dominated baseball’s annual hot stove gathering quite like the Bronx Bombers. From Hall of Fame acquisitions to record-breaking signings, the Yankees have repeatedly reshaped the American League during these four crucial days. Their track record stretches back more than six decades. And it should terrify every rival executive arriving in Florida this week.
A Yankees legacy that includes Roger Maris
The Yankees’ Winter Meetings dominance began long before Cashman took the reins. At the 1959 meetings in Miami Beach, the franchise pulled off one of the most lopsided trades in baseball history.
New York sent Hank Bauer, Don Larsen, Norm Siebern and Marv Throneberry to Kansas City for Roger Maris, Joe DeMaestri and Kent Hadley. At the time, Maris had shown little hint of future stardom. He was just 24 years old and coming off a modest season.
What followed stunned baseball. Maris led the AL with 112 RBI in his first Yankees season. He won MVP honors. The following year, he broke Babe Ruth’s single-season home run record with 61. He captured MVP again. The trade sent the Yankees to five consecutive World Series appearances from 1960 to 1964.
Twenty-five years later, the franchise struck gold again. At the 1984 Winter Meetings in Houston, New York acquired Rickey Henderson from Oakland. The Yankees sent Tim Birtsas, Jay Howell, Stan Javier, Eric Plunk and Jose Rijo to the Athletics for the future Hall of Famer.
Henderson dominated immediately. He led the league in runs scored (146) and stolen bases (80) during his first Yankees season. He finished third in MVP voting. Only Derek Jeter has recorded more stolen bases in pinstripes, and Jeter needed 2,151 more games to do it.
The Cashman era brings even bigger moves
The current general manager has turned Winter Meetings week into his personal showcase. His track record speaks for itself.
In 2008, Cashman flew from the Bellagio in Las Vegas to Northern California to close a deal with CC Sabathia. That seven-year, $161 million contract was a record for pitchers at the time. New York won the World Series the following season.
Eleven years later, Cashman struck again. Gerrit Cole signed a nine-year, $324 million deal during the 2019 meetings in San Diego. That contract became the largest ever for a pitcher. It eclipsed the $245 million Stephen Strasburg received just days earlier.
Last December in Dallas, the Yankees added Max Fried to their rotation. The left-hander agreed to an eight-year, $218 million deal. He went on to rank seventh among American League pitchers with 4.4 bWAR during the 2025 season.
But the trades have been equally explosive.
Blockbuster deals that shook baseball
At the 2017 meetings in Orlando, the Yankees stunned everyone by landing reigning NL MVP Giancarlo Stanton from Miami. Stanton had just slugged 59 home runs. He was under contract for another decade. The Marlins sent him to New York for Starlin Castro and two minor leaguers.
Then came 2023 in Nashville. Trade talks between the Yankees and Padres stalled the weekend before the meetings. New York balked at San Diego’s asking price for Juan Soto. But the two sides resumed discussions at the event and reached agreement.
The Yankees sent Michael King, Drew Thorpe, Jhony Brito, Randy Vasquez and Kyle Higashioka to San Diego for Soto and Trent Grisham. It gave New York the superstar left-handed bat they desperately needed. Soto hit a career-best 41 home runs and led them to the World Series.
The 2009 meetings in Indianapolis produced another gem. A three-team trade with Detroit and Arizona brought Curtis Granderson to the Bronx. He logged two 40-homer seasons in four years with the Yankees.
In 2022, Aaron Judge agreed to re-sign with New York during the meetings in San Diego. His nine-year, $360 million deal ended a courtship that included heavy interest from the Giants.
Budget questions add tension this time
Managing general partner Hal Steinbrenner recently said it would be “ideal” to come in lower than last year’s $319 million payroll. The Yankees already have approximately $255.8 million committed for 2026. The highest luxury tax threshold sits at $304 million.
Yet Cashman offered a revealing response when asked about adding another nine-figure contract.
“I would always do that,” he said with a grin. “I’m good at spending money.”
The bullpen struggled throughout 2025, posting a 4.37 ERA that ranked 11th in the American League. Free agency pulled Devin Williams to the Mets and Luke Weaver to the open market. Three key rotation arms face injury concerns. Gerrit Cole underwent Tommy John surgery. Carlos Rodon dealt with loose bodies. Clarke Schmidt required an internal brace procedure.
“We had a good team last year,” Cashman said, “but it’s not the same team because of free agency. We’ll see where it all takes us.”
Why the AL should be terrified
Cody Bellinger remains the top outfield target. The former MVP hit .272 with 29 home runs during his first Yankees season. He provided balance to a left-handed heavy lineup thanks to a reverse split that saw him hit .353 against southpaws.
Cashman has been direct about his preference for a reunion. But Bellinger seeks a lucrative long-term deal. Kyle Tucker offers an alternative, though he could command north of $400 million.
The Marlins have discussed Sandy Alcantara with New York. Miami has also fielded inquiries about Edward Cabrera. Top prospects Spencer Jones and Jasson Dominguez could become trade chips.
Toronto signed Dylan Cease to a seven-year, $210 million contract earlier this week. Boston added Sonny Gray and Johan Oviedo. The AL East arms race continues.
Aaron Judge has won three of the last four AL MVP awards. He captured the 2025 batting title. He has made one thing clear. He would trade every individual honor for a championship ring.
The Yankees have not won a World Series since 2009. That drought haunts everything the organization does. But history tells us something important about this franchise and this week.
When the Winter Meetings begin, the Yankees make things happen. They have done it for more than 65 years. Rival executives know this. And that knowledge should keep them up at night in Orlando.
What do you think? Leave your comment below.
