1990 Winter Meetings: They Almost Didn’t Happen

This article was written by John J. Burbridge Jr.

This article was published in Baseball’s Business: The Winter Meetings: 1958-2016

Baseball's Business: The Winter Meetings: 1958-2016


The Winter Meetings of 1990 were held amid a dispute between the major and minor leagues and uncertainty arising from an agreement between the major-league owners and the players union concerning collusion. The minor leagues were mainly asking for additional support for their farm teams from the major-league parent. With respect to the collusion issue, the union had charged that the owners had colluded with each other during the latter part of the 1980s, and such collusion resulted in market issues for free-agent players. An agreement between the owners and the union was announced one month before the scheduled Winter Meetings, but since details of the agreement had not been fully established at the time of the announcement and the subsequent Winter Meetings, a lingering uncertainty remained.

The Dispute

In early May of 1989 David Simon, the president of the Los Angeles Sports Council, announced that the 1990 Winter Meetings would be held in Los Angeles.1 However, a cloud hovered over these meetings in the form of a dispute between the major and minor leagues concerning the contract between the two parties. The National Association of Professional Baseball Leagues (NAPBL), the minors’ umbrella organization, which was in charge of scheduling and organizing the Winter Meetings, was questioning several issues, including the amount of compensation to be paid directly to the minor-league clubs by the major-league parent. Commissioner Fay Vincent also advocated improving salaries and working conditions for minor-league umpires.2

Both parties agreed that if an agreement was not reached before November 1, 1990, the combined Winter Meetings would be canceled and the major leagues and minor leagues would meet separately. No agreement was reached, and the 26 major-league clubs pulled out of the Los Angeles meetings.3 Bill Murray, chief negotiator for the major leagues, said they hoped the dispute would be settled by November 15, but that would be too late to have the combined meetings.4 Major-league officials also announced that they would attempt to set up alternate meetings for their clubs, while the NAPBL took the position that the meetings would be held in Los Angeles with or without the participation of the major-league clubs.

Quickly reacting to the situation, the commissioner’s office rescheduled the major-league portion of the meetings for the Hyatt Rosemont Hotel at O’Hare Airport in Chicago. Reflecting on the situation, Roland Hemond, general manager of the Baltimore Orioles, said there was no substitute for one-on-one trade discussions. “In a face-to-face setting, you have the principals of each club involved,” he said. “You might have your club president, your manager, your owner present. That gives you the opportunity to caucus for a few minutes, have a quick discussion and come back and say, ‘You’ve got a deal.’ When you do it over the phone, you might have to go back and talk to your people and they have to talk to theirs. There’s more time for something to get in the way of a deal.”5

By November 15 the dispute still was not settled. The contract had an end date of January 12, 1991. As that date neared, it was reported that Major League Baseball was making plans for a reorganized system of minor leagues that could include as many as 170 teams.6 This never materialized, because an agreement was reached in early December of 1990.

The Collusion Agreement

In September 1990 George Nicolau, an arbitrator, found baseball owners guilty of collusion in their treatment of free agents after the 1987 and ’88 seasons. He ruled that baseball club owners must pay players a total of $102.5 million in lost salary for those years. Another arbitrator, Thomas Roberts, had previously awarded $10.5 million for lost salary in 1986, for a total $113 million in damages. The two sides still had to settle or have decided four other issues: (1) damages for lost 1989 and 1990 salaries, (2) interest on all the damages awarded, (3) second-look free agency for 21 former free agents, and (4) damages on individual claims for such matters as lost mobility.7 On the day the arbitrators announced the award, Charles O’Connor, the owners’ chief labor representative, stated that all the details with respect to the collusion agreement could be resolved by the end of 1990.8

On November 3, 1990, it was announced that the club owners had agreed to pay $280 million in damages, to end the efforts of the union in its conspiracy cases against the owners.9 However, no determination had been made as to how many players would share in the settlement, or how money would be distributed. Donald Fehr, director of the players’ union, said, “There’s been a tentative understanding reached by the lawyers. It’s subject to working out a lot of details.”10

It was also agreed that new-look free agent status would be granted to 16 players who had been free agents after the 1987 season.11 These free agents and their appropriate teams were:

  • Jack Morris, Detroit
  • Dave Smith, Houston
  • Mike Witt, New York Yankees
  • Dave LaPoint, New York Yankees
  • Dennis Martinez, Montreal
  • Danny Darwin, Houston
  • Larry Andersen, Boston
  • Juan Berenguer, Minnesota
  • Mike LaCoss, San Francisco
  • Charlie Leibrandt, Atlanta
  • Mike Heath, Detroit
  • Jack Clark, San Diego
  • Gary Gaetti, Minnesota
  • Brett Butler, San Francisco
  • Dave Henderson, Oakland
  • Chili Davis, California

However, these 16 players were not to actually become free agents until the two sides ratified the collusion settlement.

While this collusion agreement was not necessarily directly related to the 1990 Winter Meetings, the agreement and the fact that ratification had to occur before the 16 players became free did permeate the atmosphere of the meetings and affected some of the signings and transactions.

First Joint Venture

Against that backdrop, the Major League Winter Meetings kicked off with a state-of-the game address by Commissioner Fay Vincent. The commissioner was at home in Connecticut due to a bout of pneumonia and his address was read at the meeting. Vincent called for the creation of a program to better prepare young players for the pressures of the major leagues. Vincent portrayed this effort, plus the imminent naming of a joint committee to study the economics of baseball, as attempts to improve the relations between the parties. He also commented on the collusion agreement: “Should it be approved, then finally we can put this episode behind us for good and move forward.”12

Donald Fehr, executive director of the players union, was invited to join the leadership of the joint venture and agreed to present Vincent’s proposal to the union. Fehr also offered a note of caution: “The fact is, if the relationship improves, it hinges almost entirely on whether the collusion settlement goes through and whether the free-agent market continues to show signs that it is operating and well. If the relationship does improve, everybody has to be encouraged. It doesn’t mean you agree on everything; if it could avoid unnecessary squabbling, that would be a step in the right direction.”13

Rule 5 Draft

The Rule 5 Draft was a Winter Meetings fixture. Players eligible for the draft were those not on their team’s 40-man roster who either signed initial contracts at 19 or older and had spent three or more years in the minor leagues, or signed their initial contract when younger than 19 and had spent four or more years in the minor leagues.14

The price to draft a player was $50,000. A drafted player must remain on the drafting team’s 25-man roster or be offered back to his original club for $25,000. If a team did not have space on its 40-man roster, it could not participate. The following players were drafted:

Player Drafting
Pat Howell Minnesota Twins New York Mets
Mike Huff Cleveland Indians Los Angeles Dodgers
Greg McCarthy Montreal Expos Philadelphia Phillies
Nikco Riesgo Montreal Expos Philadelphia Phillies
Frank Seminara San Diego Padres New York Yankees
Doug Simons New York Mets Minnesota Twins
Ed Taubensee Oakland Athletics Cincinnati Reds
Dean Wilkins Houston Astros Chicago Cubs

Free Agent Signings

With the meetings occurring just slightly more than a month after the majors and minors chose to hold separate meetings, one might assume that the amount of activity would be less than usual. However, the opposite was true, as the 1990 meetings proved to be memorable in terms of free-agent signings and trades.

On December 3, there was a flurry of free-agent signings. The San Francisco Giants, convinced that their center fielder, Brett Butler, a new-look free agent, would be leaving the club, signed the 1990 National League batting champion, Willie McGee, to a four-year contract worth $13 million and indicated they would not make a serious attempt to re-sign Butler. Not wanting to go into 1991 without a center fielder, Giants president and general manager Al Rosen grabbed McGee.15

McGee had actually finished the 1990 season in Oakland, and once he moved across the Bay Bridge, the A’s responded by getting Willie Wilson to commit to a two-year contract. Wilson had spent his entire 15-year career with the Kansas City Royals, where he won a batting title (1982) and a stolen-base crown (1979), was named to two All-Star teams, and helped the Royals win the 1985 World Series. Other signings announced on December 3 were third baseman Terry Pendleton signing with the Atlanta Braves for four years at $9.8 million; right-handed pitcher Kevin Gross signing a three-year deal with the Los Angeles Dodgers; and the Detroit Tigers inking right-hander Bill Gullickson. Pitcher Dennis Martinez, another new-look free agent righty, decided not to test free agency but announced that he was staying with the Montreal Expos for a three-year contract believed to be worth $9.5 million.16

December 4 saw second baseman Steve Sax sign a four-year deal with the New York Yankees, reportedly worth $12.4 million. Yankees Vice President George Bradley said of the deal, “He is a winning ballplayer and along with Mattingly gives us the start of a solid nucleus to build the club around.”17 The Brewers announced that right-handed reliever Edwin Nunez had signed a two-year contract. The Giants continued being active by signing left-hander Dave Righetti for four years at $10 million, while the Boston Red Sox also signed a southpaw, one-time All-Star Matt Young.

The signings continued on December 5 and 6. On December 5, the Atlanta Braves signed first baseman Sid Bream, the Mets signed outfielder Vince Coleman in an attempt to replace Daryl Strawberry (who had previously signed with the Los Angeles Dodgers), and the Milwaukee Brewers signed first baseman-outfielder Franklin Stubbs. The following day, two outfielders inked new contracts as the Cubs signed George Bell, the 1987 AL MVP, while the Orioles grabbed eight-time Gold Glove winner Dwight Evans.

The Trade

The 1990 Winter Meetings are mainly remembered today for one of the most significant offseason trades in the history of baseball. The seeds for such a deal were planted during the World Series. Toronto Blue Jays general manager Pat Gillick and Joe McIlvaine, the new general manager of the San Diego Padres, discussed outfielder Joe Carter, who had been acquired by San Diego the year before and had led the Padres in RBIs. Gillick followed up with McIlvaine at the general manager meetings, and their discussion resumed at the Winter Meetings. On December 4 McIlvaine proposed a swap of Joe Carter for Toronto first baseman Fred McGriff. McIlvaine knew that Toronto needed to make room for young first baseman John Olerud, and the Padres needed a first baseman with Jack Clark about to become a new-look free agent. Toronto had also lost outfielder George Bell, who was about to sign with the Chicago Cubs, and needed an outfielder to replace him.

While Gillick was willing to deal McGriff, he had problems with a one-for-one swap given that McGriff was three years younger than Carter. Gillick suggested that Roberto Alomar, the young switch-hitting second baseman for the Padres, be included in the deal. Alomar was already a three-year veteran at the age of 22. McIlvaine was supposedly aware that there were issues between Alomar and his manager, Greg Riddoch. However, McIlvaine was not willing to give up two players for McGriff.

Garry Templeton was the San Diego shortstop and was nearing the end of his career. McIlvaine wanted to replace him and envied Toronto’s Tony Fernandez, a smooth fielding, switch-hitting shortstop. McIlvaine was not optimistic that Toronto would trade Fernandez but Gillick supposedly felt his shortstop was somewhat moody and was willing, provided he got Alomar.

On December 5, 24 hours after the initial discussions at the Winter Meetings, McIlvaine mounted a podium in one of the meeting rooms, said, “We thought we’d give you a good old-fashioned baseball trade,” and announced that Joe Carter and Roberto Alomar would be going to Toronto for Fred McGriff and Tony Fernandez.18 No money changed hands.

While the reaction was somewhat mixed as to who got the best of the deal, many realized that Alomar had the highest upside. Jack McKeon, who had been both a manager and general manager for San Diego in 1990, said in 2012 that he would have never considered trading Alomar.19 Alomar and Carter led Toronto to World Series victories in 1992 and 1993, and Alomar was elected to the Baseball Hall of Fame. McGriff won a home-run title for San Diego in 1991, then was traded to Atlanta, where he helped the Braves win the 1995 World Series. Fernandez, on the other hand, did not last long with San Diego and eventually returned to Toronto.

Other Significant Trades

At the beginning of the meetings, the California Angels traded right-handed pitchers Willie Fraser and Marcus Moore and outfielder Devon White to Toronto for infielder Luis Sojo, outfielder Junior Felix, and a player to be named later, who turned out to be minor-league catcher Ken Rivers.

On December 3, the New York Yankees traded outfielder Oscar Azocar to the San Diego Padres for a player to be named later (outfielder Mike Humphreys).

On December 4, several deals were announced. The Baltimore Orioles traded outfielder Dave Gallagher to the Los Angeles Angels for two minor-league pitchers, lefty Mike Hook and right-hander Dave Martinez. The Chicago White Sox dealt right-handed pitchers Shawn Hillegas and Eric King to the Cleveland Indians for outfielder Cory Snyder and minor-league infielder Lindsay Foster. The Oakland Athletics traded outfielder Darren Lewis and a player to be named later (minor-league right-hander Pedro Pena) to San Francisco for infielder Ernie Riles.

The following day saw one more deal, as the Giants traded right-handed relief pitcher Steve Bedrosian, the 1987 National League Cy Young Award winner, to the Minnesota Twins for right-handed pitcher Jimmy Ard and a player to be named later (minor-league southpaw Jimmy Williams). This concluded a very active Winter Meetings for the Giants.


Today, the 1990 Winter Meetings are viewed as being quite memorable. What most fans of the game remember is the trade of a future Hall of Famer.20 There can be no doubt that the trade of Roberto Alomar was a significant factor in the Toronto Blue Jays winning two pennants and two World Series. The business side of the game is also remembered for the major leagues organizing their own meetings in Chicago, independent of the NAPBL. The collusion agreement also cast a cloud over the meetings as it forced teams to evaluate their positions and led to some fascinating free-agent signings. It is also interesting to note that many in the baseball community felt that the collusion agreement would result in greater harmony between the owners and the players union. However, as the history of the 1990s tells us, this wasn’t to be the case.



1 “Baseball’s 1990 Winter Meetings Will Be Held in Los Angeles,” Los Angeles Times, May 2, 1989.

2 Peter Schmuck, “Major-League Clubs Withdraw From Winter Meetings,” Baltimore Sun, November 2, 1990.

3 Ibid.

4 articles.philly.com/1990-11-01/sports/25929736_1_major-leagues-minor-leagues-national-league.

5 Peter Schmuck, “Hemond Is Looking to Raise Trade Heat at Winter Meetings,” Baltimore Sun, November 30, 1990.

6 Claire Smith, “Baseball; Baseball Is Scouting Minor League Homes,” New York Times, November 20, 1990.

7 Murray Chass, “Players Get $102.5 Million in Collusion Case,” New York Times, September 18, 1990.

8 Ibid.

9 Ibid.

10 Ibid.

11 Ibid.

12 Claire Smith. “Baseball; Union-Management Plan to Help Young Players,” New York Times, December 4, 1990.

13 Ibid.

14 baseball-reference.com/bullpen/Rule_V_Draft.

15 Peter Schmuck, “Giants Get McGee as Butler Insurance/Winter Meetings Notes,” Baltimore Sun, December 4, 1990.

16 Michael Bamberger, “Free-Agent Signings Dot Winter Meetings,” philly.com, December 4, 1990.

17 Peter Schmuck, “Orioles Make Pitch to Price/Winter Meetings Notes,” Baltimore Sun, December 5, 1990

18 Brent S. Gambill, “Anatomy of a Trade: The 1990 Padres-Blue Jays Blockbuster,” baseballprospectus.com/article.php?articleid=19068.

19 Ibid.

20 Tyler Kepner, “A Blockbuster That Proved Worthy of the Hall of Fame,” New York Times, January 5, 2010.