End-of-year deals: Here are the Padres' top 5 December trades

December 1st, 2022

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The Winter Meetings arrive in San Diego next week, and if history is any indication, it should be a busy month for the Padres.

This team has quite a history of wheeling and dealing in December. Not every one of those moves has worked out, but the Padres have long been one of the sport's most active dealmakers -- from Trader Jack McKeon to Gunslinger Kevin Towers to the current tenure of general manager A.J. Preller.

In honor of another Winter Meetings in San Diego -- now three in the past nine years -- here's a countdown of the five biggest December trades in franchise history:

5) Myers arrives; Turner we hardly knew ya
Dec. 19, 2014
Padres got: OF , C , LHP José Castillo, RHP
Nationals got: RHP , SS
Rays got: OF , C René Rivera, RHP , OF , LHP Travis Ott

Preller's first Winter Meetings in charge of the Padres should've given us a decent idea of what was going to come. In an ill-fated attempt to contend in 2015, the Padres overhauled their roster in December, adding the likes of Matt Kemp and Justin Upton. Later that offseason, James Shields and Craig Kimbrel arrived.

The biggest blockbuster of the bunch was this three-team, 11-player deal that saw Myers arrive in San Diego. Eight years later, the hindsight on this trade isn't particularly pretty. Both Turner and Myers are free agents. Turner is a two-time All-Star and one of the best shortstops in the game. Myers' Padres tenure, meanwhile, featured ups and downs too numerous to count.

That said, Myers established himself as a fan favorite across his eight seasons. San Diego also landed Castillo in that deal, now the longest-tenured Padre in Myers' absence.

4) Off to trade the Wizard 
Dec. 10, 1981 
Padres got: SS Garry Templeton, OF Sixto Lezcano, RHP Luis DeLeon 
Cardinals got: SS , RHP Steve Mura, LHP Al Olmsted

Of all the lopsided deals in Padres history -- and there have been many -- this might be the most unfortunate. Smith had established himself as a defensive force at shortstop in San Diego, though he hadn't fully developed into the hitter he would become.

In the offseason of 1981-82, the Padres sent Smith to St. Louis for a trio of players, headlined by Templeton. A like-for-like replacement at short, Templeton spent 10 very useful seasons in San Diego and is enshrined in the Padres Hall of Fame. He was integral in the team’s push for its first pennant in 1984.

But there's really no comparison here. Smith went on to a Hall of Fame career as one of the best shortstops in baseball history.

3) Padres land their ace 
Dec. 15, 1997 
Padres got: RHP   
Marlins got: 1B , LHP Steve Hoff, RHP Rafael Medina

The Padres felt they had the pieces in place to contend in 1998, but they needed a front-line starter. So after the ‘97 Winter Meetings in New Orleans, the Padres struck a deal with the Marlins to land Brown, who was coming off a dominant postseason with Florida.

Brown was entering the final year of his contract, and he would only spend one season in San Diego. But that season was perhaps the best pitching season in franchise history. He posted a 2.38 ERA with 257 strikeouts in 257 innings. He finished third for the NL Cy Young Award -- which went to Atlanta’s Tom Glavine -- having split votes with teammate and Hall of Fame closer Trevor Hoffman, who finished second.

Then, in the postseason, Brown was utterly dominant once again, pitching the Padres to their first pennant since 1984. Lee would go on to have a heck of a career, but Brown's contributions in the ‘98 season alone make this trade worth it. (I've said it before in this space, and I'll say it again: Brown's Hall of Fame case deserves a second look.)

2) Building a contender
Dec. 28, 1994
Padres got: 3B , OF , 1B , SS , RHP Brian Williams, LHP Sean Fesh
Astros got: OF Derek Bell, RHP , INF , LHP , OF , INF Craig Shipley

Look no further than this trade for the moment in the mid-'90s when the Padres shifted from also-ran to contender.

"We really needed an attitude pick-me-up," Hoffman told me a couple of years ago when I dived into some of the moves that preceded this trade. "Those two guys in particular brought that confidence to the team. Obviously, we were still transitioning from fire-sale trades to an organization looking for its identity."

The Padres found that identity with the arrival of Caminiti and Finley, staples on the 1996 and '98 NL West champions. Caminiti won the ’96 NL MVP Award and is perhaps the best third baseman in franchise history (though likely to be surpassed imminently by Manny Machado). Finley, meanwhile, won two of his five Gold Gloves in San Diego and registers as perhaps the top center fielder in franchise history.

No, they didn't come cheap. This deal was a 12-player behemoth. But it's hard to argue the Padres didn’t get the better of this one. The trade was mostly agreed upon prior to Thanksgiving, but with San Diego’s ownership in flux, it wasn't finalized until well after the 1994 Winter Meetings and even beyond Christmas.

1) A true Winter Meetings blockbuster
Dec. 5, 1990
Padres got: 1B , SS
Blue Jays got: 2B , OF

Was this the biggest swap in Winter Meetings history? You could certainly make a case, considering the caliber of players moved in the deal. Doris Gillick, the wife of Blue Jays GM Pat Gillick, famously told her husband, "Will you get home before you screw up the team any further?"

That deal, of course, worked out well for Toronto. Alomar became a Hall of Fame second baseman. Carter was a five-time All-Star who walked off a World Series. The Blue Jays won two of those in the three years after this deal.

The Padres’ side of that trade is largely derided. To some extent, I think that’s a bit unfair. McGriff was a Hall of Fame-caliber first baseman and Fernandez was an outstanding shortstop.

From my perspective, the Padres’ biggest sin wasn't making this trade. They dealt two excellent players and landed two excellent players in return. No, their biggest mistake in a trade like this one was letting both McGriff and Fernandez leave via separate trades within the next 2 1/2 years.