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Last month, the Toronto Blue Jays made their largest trade in franchise history, acquiring stars Jose Reyes, Mark Buehrle, and Josh Johnson. However, only time will tell if that trade also becomes the most impactful swap in team history. For now, that designation remains with the most memorable trade in Winter Meetings history.

During the 1990 Winter Meetings in Los Angeles, more than $100 million—at the time, a massive sum—was spent on free agents. Franklin Stubbs became the most unlikely free agent multimillionaire as Milwaukee Brewers General Manager Harry Dalton signed him to a three-year, $6 million contract. The Atlanta Braves set up their 1991 World Series run by signing free agents Sid Bream and future 1991 National League MVP Terry Pendleton. The St. Louis Cardinals lost free agents Pendleton, Willie McGee, and Vince Coleman, ending their 1980s run of success. Kevin Gross joined another recent free agent signee, Darryl Strawberry, with the Los Angeles Dodgers. In 1990, player salaries increased by $100,000 per player. It was one of the most active Winter Meetings in baseball history, but it is remembered for one blockbuster trade between the Blue Jays and San Diego Padres.

1990 San Diego Padres
Before the 1990 blockbuster, Padres General Manager Jack McKeon made the most memorable trade of the 1989 Winter Meetings. On December 6, 1989, McKeon acquired Joe Carter from the Cleveland Indians for Sandy Alomar, Jr., Carlos Baerga, and Chris James. This trade would eventually help set up the strong Indians teams of the late 1990s.

In April of 1990, Tom Werner led an investment group of 10 Los Angeles and San Diego businessmen to purchase the Padres from their long-time owners, the Kroc family. On June 14, 1990, Werner’s group was approved as the new owners of the Padres, paying approximately $75 million.

At midseason, Greg Riddoch was named manager, replacing McKeon, who had gone 37-43 on the season. Riddoch would finish the season with one more win and loss than his predecessor at 38-44. McKeon had remained general manager, but he was fired on September 21st. Joe McIlvaine was named the new GM of the Padres on October 2nd.

1990 Toronto Blue Jays
In 1990, Cito Gaston began his first full season as manager. In 1989, he had replaced Jimy Williams as manager after the Jays’ 12-24 start to the season. Williams was the first in-season managerial firing in club history.

In its first full season in the SkyDome, the franchise drew a record 3.9 million fans. The Blue Jays finished second in the AL East and three games under their 1989 win total with an 86-76 record.

The foundation of the deal began over a casual discussion between GMs about Joe Carter at the 1990 World Series. At the GM Meetings, Blue Jays General Manager Pat Gillick followed up, asking McIlvaine if he would consider trading Carter. He was quickly rebuffed. In Carter’s first year in San Diego, he had set the club record for RBIs in a season.

When talks resumed at the Winter Meetings at mid-afternoon on Tuesday, December 4th, McIlvaine suggested a one-for-one swap: Carter for first baseman Fred McGriff. McIlvaine correctly believed that John Olerud was ready to take over at first base for Toronto if McGriff was dealt. Blue Jays manager Cito Gaston wanted to get Olerud into the lineup and expected him to replace the bat of departing free agent right fielder George Bell.

The Padres were losing first baseman Jack Clark to free agency, so they needed a replacement. A 27-year-old power-hitting first baseman would be the ideal replacement. McGriff had also batted .300 to Carter’s career-low .232 the previous season. San Diego had offered Clark a one-year, $2.5 million contract, but the trade effectively ended their negotiations. He eventually signed a three-year, $8.7 million contract with the Boston Red Sox.

For Toronto, Carter would be the ideal replacement for former MVP Bell in the outfield. Bell had been an All-Star in 1990, but he slumped during the final two months of the season as he battled a bruised hand and fluid in his eye, and he was never again able to match his career-best and MVP season of 1987. The Blue Jays offered him a one-year deal as a designated hitter but did not expect him to accept. At the end of the Winter Meetings, Bell signed a three-year, $9.8 million deal with the Chicago Cubs.

Gillick knew McGriff was three years younger than Carter and entering his prime, so he suggested adding switch-hitting second baseman Roberto Alomar to the deal. McIlvaine was aware that Alomar had feuded with new Padres manager Riccoch during the season. His father, Sandy, was a San Diego coach. With Bip Roberts and Joey Cora on the roster, he believed he could fill second base with either or both in a platoon.

At age 22, Alomar was already a three-year veteran, having debuted at age 20. He was considered the player with highest upside in the trade. Former General Manager Jack McKeon has stated that he would never have considered dealing Alomar. If not for the ownership and front office changes, we might be looking at Alomar in a Padres cap on his Hall of Fame plaque.

The Padres believed long-time Padres shortstop Gary Templeton was nearing the end of his career. McIlvaine did not think he was capable of being an everyday shortstop any longer at age 34, so he asked Toronto about switch-hitting shortstop Tony Fernandez. He did not expect that the Blue Jays would consider moving the four-time Gold Glove winner. However, Gillick was open to dealing the sometimes moody shortstop, but only if Alomar was included. Within moments, a deal was struck. McIlvaine and Gillick looked at each other and laughed in disbelief. They agreed to sleep on it.

McIlvaine called first thing Wednesday morning and agreed to complete the deal. In essentially 24 hours, one of the most famous trades in baseball history was completed. The two GMs met at 2 p.m. to review the trade, and a press conference was scheduled for an hour later.

Trade reporting was different in 1990 than it is today. There was no Twitter or 24-hour news coverage. Press conferences could still surprise with announcements of genuine breaking news, since there was no hint of the deal before the announcement.

Gillick had been acting General Manager of the Blue Jays since 1977. At the time, he had not made a trade in five years. He was commonly called by the nickname, “Stand Pat”. This was his first trade at the Winter Meetings in seven years.

McIlvaine stepped to the podium in the TWA-Northwest room of the O’Hare Hyatt Regency and said, “We thought we’d give you a good old-fashioned baseball trade.” He then announced the player names in the trade. According to multiple reports, the audience of reporters and television crews gasped as the names of players in the trade were announced. In the back of the press conference, Frank Robinson gasped along with the media crowd.

Next to Robinson stood always-gregarious Los Angeles Dodgers manager Tommy Lasorda, who applauded. Most believed that the Padres had gotten the better of the deal, but Lasorda was not one of them. Instead, he subscribed to the old baseball axiom that whichever team gets the best player wins the deal.

Lasorda had watched Roberto Alomar play for three seasons and believed the best player was headed out of the NL West to Toronto. Two World Series titles, 12 All-Star appearances, and a Hall of Fame plaque later, Lasorda was proven correct, as was Hall of Fame GM Pat Gillick.

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Gillick "had not made a trade in five years" at the time? Are you missing a qualifier because that's just not true.
Didn't the Jays get Devon White from the Angels the previous day? I seem to remember a "whole new OF" narrative for some reason - plus I loved Junior Felix and he was in that White trade.
And what about Jesse Barfield for Al Leiter? Maybe that was in the season after Carter was acquired...I should check B-ref, but don't feel like it.
Fascinating. Great read.