Winter Meetings underway: All you need to know

In most industries, meetings are a bore and chore. They consist of PowerPoints, "action items" and "check-ins," and the end result, usually, is just an agreement to "circle back" to everything at yet another meeting at a later date. Meetings are a necessary evil, a means to an end, an annoyance on your Outlook calendar.

But just as the concept of "touching base" takes on a different connotation in the baseball world than the business world, so, too, do meetings themselves. The phrase "Winter Meetings" has a titillating tenor to it. It conjures up images not of action items but actual action. We think of it as the event where the baseball world convenes and big deals get done.

They are, in short, meetings you can actually get excited about.

With the 2019 Winter Meetings about to begin at San Diego’s Manchester Grand Hyatt on Monday, here's a primer on what this annual event is all about.

What is it?

The Winter Meetings are an industry gathering. Representatives from all 30 teams and their various affiliates attend the Winter Meetings. Executives, team staff, media, exhibitors and job seekers converge to network with peers, fill job and internship vacancies, attend workshops, discuss trends and exchange ideas. In some ways, it isn't terribly different from, say, an accountants' conference, because it features a trade show, a job fair, seminars, luncheons, etc.

A key difference is that accountants don't typically gather together in hotel suites and devise ways to trade their clients or sign them to multimillion dollar contracts.

That's why we love the Winter Meetings.

Why does it matter?

Though the ubiquity of texting and e-mailing has altered the dynamics of the Meetings as much as it has altered the fabric of our daily lives, team executives still view the Winter Meetings as a productive place to conduct offseason business.

The convergence of team decision-makers and agents in a single building -- a building many of them will not leave at all for four days -- can accelerate action. It is an efficient environment for deal-making because of the ease of face-to-face dialogue (agents will sometimes fly clients to the Meetings so they can make and listen to pitches in person) and, sometimes, the competitive spirit that kicks in when everybody gets together under one roof.

What happens?

Folks typically arrive on Sunday and depart on Thursday. Team executives usually line up meetings with other clubs and with agents throughout Monday, Tuesday and Wednesday. General managers usually have a daily discussion with the local beat reporters to keep them abreast of where things stand, and each Major League manager conducts a press conference where questions about the state of the club are fielded. Reporters mill about the hotel lobby, seeking out team and agent sources, gathering information and, yes, spreading rumors.

When a deal actually gets done, the involved club or clubs hold a press conference in the media work room. If it's a free-agent deal or major trade completed in time for the player to travel to the site, it is not unusual for the player to attend the press conference. That's what happened when the Yankees unveiled Giancarlo Stanton at the 2017 Winter Meetings in Lake Buena Vista, Fla., for instance.

What are some notable deals that have gone down there?

In 1975, the always enterprising owner Bill Veeck, having just recently purchased the White Sox, set up a table at the Winter Meetings in Fort Lauderdale, Fla., with a sign that read, "Open for Business." He went on to make six trades involving 22 players that week.

The Winter Meetings aren't always that lively, but plenty of big deals have gone down there over the years. In free agency, Barry Bonds (1992, Giants, $43 million), Kevin Brown ('98, Dodgers, $105 million) and Alex Rodriguez (2000, Rangers, $252 million) all set new records with contracts completed at the Winter Meetings. Brian Cashman's abrupt exit at the Bellagio in Las Vegas in '08 to fly to California to nail down a $161 million deal (at the time, a record for a pitcher) with CC Sabathia was memorable, as was Albert Pujols' mega pact with the Angels that was negotiated at the '11 Winter Meetings and completed just as everybody was packing up.

As far as trades are concerned, the Yankees' 1959 acquisition of Roger Maris, the Orioles' '65 trade for Frank Robinson, the Mets' '84 deal for Gary Carter, the '90 Padres-Blue Jays blockbuster that involved Fred McGriff, Joe Carter, Tony Fernandez and Roberto Alomar, the Tigers' franchise-altering trade for Miguel Cabrera in 2007 and the Red Sox's '16 acquisition of Chris Sale are some of the standout swaps that have taken place at the Winter Meetings.

What else is announced at the Winter Meetings?

On Sunday, a National Baseball Hall of Fame Eras Committee gathers at the Winter Meetings to discuss and vote on that year's ballot, be it the Today's Game (for candidates whose greatest contributions to baseball were realized from 1988 to the present), Golden Days (for candidates whose greatest contributions to baseball were realized from '50-69), or Early Baseball (for candidates whose greatest contributions to baseball were realized prior to '50). Those candidates who appear on 75 percent of ballots cast get inducted into the Hall of Fame the following summer, alongside the Baseball Writers' Association of America selections.

This year, the 16-member Modern Baseball Era Committee elected the late former MLBPA director Marvin Miller and longtime catcher Ted Simmons to Cooperstown. More >

What is the Rule 5 Draft?

The Rule 5 Draft is the annual grand finale of the Winter Meetings, taking place on Thursday morning as executives prepare to depart. It is an opportunity for teams to take a chance on untapped talent and, while the players involved are little more than lottery tickets, it has uncovered some real gems over the years.

The Rule 5 Draft involves players who were left off their team's 40-man roster and were either A. signed at age 19 or older and have played in professional baseball for at least four years or B. signed at 18 or younger and have played for at least five years. A team that selects a player in the Rule 5 Draft pays $100,000 to the team from which he was selected, and the receiving team must keep the player on the Major League 26-man roster or injured list (though the player must be active for at least 90 days) for the entirety of the following season. If the player does not remain on the roster, he must be offered back to the team from which he was selected for $50,000. All players on a team's 40-man roster are "protected" from the Rule 5 Draft, and only teams with vacancies on their 40-man at the time of the Draft can participate (in reverse order of the previous season's standings). It is conceivable that there will be more Rule 5 activity this year, with the 2020 expansion of active rosters from 25 to 26 players.

Roberto Clemente, Johan Santana, Dan Uggla, Josh Hamilton and Joakim Soria are the most famous examples of impact players who were acquired in the Rule 5 Draft. There are also Triple-A and Double-A phases of the Draft.