Padres' 5 biggest Winter Meetings moves 

SAN DIEGO -- From “Trader Jack” McKeon to “gunslinger” Kevin Towers to current general manager A.J. Preller, Padres execs have developed quite a reputation for wheeling and dealing.

They’ve done some of their most noteworthy business at the Winter Meetings. Here's a look back at the five most impactful Winter Meetings transactions in Padres history:

1) Padres deal Alomar, land Fernandez and McGriff
Date: Dec. 5, 1990
Transaction: Padres trade Roberto Alomar and Joe Carter for Tony Fernandez and Fred McGriff

In the New York Times' account of this trade, Blue Jays general manager Pat Gillick was derided by his own wife for dealing Fernandez and McGriff at the Meetings and told to "get home before you screw up the team any further." In retrospect, however, Gillick and the Blue Jays are clear winners. Alomar was a solid player in San Diego, but he blossomed into a Hall of Famer in Toronto. Of course, McGriff is a Hall of Famer as well, and Fernandez was an excellent player in his own right. Both thrived in San Diego, and any rancor about the decision to move Alomar needs to be tempered by the return. The biggest gripe Padres fans should have is the fact that both McGriff and Fernandez were dealt two years later, for a pittance in both cases.

2) A Juan Soto blockbuster (again)
Date: Dec. 7, 2023
Transaction: Padres trade OFs Juan Soto and Trent Grisham to Yankees for RHPs Michael King, Drew Thorpe, Randy Vásquez, Jhony Brito and C Kyle Higashioka

Sixteen months after the Padres landed Soto in a Trade Deadline blockbuster, they traded him away in a December deal for the ages. With the clock ticking down on the 2023 Winter Meetings in Nashville, Preller came to an agreement with the Yankees. Soto was headed to New York. The Padres would get five pieces in return, headlined by King and Thorpe (the top prospect eventually sent to the White Sox in the Dylan Cease deal). It seemed impossible at the time, but the Padres actually got back value, despite shipping out one of the best players in baseball. They fortified their rotation in a major way, and it's hard to envision their 93-win season without the pitching they acquired. Of course, Soto would lead the Yankees to the American League pennant. In the end, this may have been the rare deal in which both sides were perfectly content with the return.

3) The Padres get their ace
Date: Dec. 15, 1997
Transaction: Padres trade Derrek Lee, Rafael Medina and Steve Hoff to the Marlins for Kevin Brown

The Marlins were coming off a World Series title and looking to sell. The Padres were on the cusp of a run to the World Series and looking to buy. The two sides came to an agreement on the final day of the 1997 Meetings in New Orleans. Brown had only one year remaining on his contract, but he made the most of it. There's an argument to be made that Brown's '98 season is the most impactful single season in franchise history. He posted a 2.38 ERA with seven complete games and three shutouts, then dominated in the postseason as well. Brown was the biggest catalyst for the Padres' run to their second National League pennant in '98.

4) The Wizard goes to St. Louis
Date: Dec. 10, 1981
Transaction: Padres trade Ozzie Smith and Steve Mura to the Cardinals for Sixto Lezcano, Garry Templeton and Luis DeLeon

It's a dubious distinction that the Padres have traded away two Hall of Fame middle infielders at various Winter Meetings. Smith was already a wizard at shortstop when the Padres decided to move him at the 1981 Winter Meetings in Hollywood, Fla. But he wasn't producing much at the plate, so the Padres dealt him for Lezcano, Templeton and DeLeon. All three were useful pieces in San Diego, and Templeton currently resides in the team's Hall of Fame. But for all the brilliant maneuvering by McKeon, this is one he'd surely like to have back.

5) Preller's spree starts with Kemp
Date: Dec. 18, 2014
Transaction: Padres trade Yasmani Grandal, Zach Eflin and Joe Wieland to the Dodgers for Matt Kemp and Tim Federowicz

San Diego played host to the 2014 Winter Meetings, and newly hired general manager Preller did his part to make things interesting. The entire week was a frenzy of Padres rumors, culminating with an agreement to send Kemp to San Diego. The move was the first domino in Preller's wild first offseason. A week later, the deal was finalized -- as were two others. The Padres landed Justin Upton from Atlanta and Wil Myers from Tampa Bay. Prior to the 2015 season, Preller also added Craig Kimbrel, B.J. Upton and James Shields to that haul. The fruits of those moves? A 74-88 record in 2015 and a teardown the following season.