When all 30 Major League Baseball clubs and the media that covers them gather for the first Winter Meetings since 2019, it will be in the same location as the last: the Manchester Grand Hyatt in San Diego, CA.

Three years and one pandemic later, not to mention a 99-day lockout last offseason, the Hot Stove League will take center stage from December 4-8 as free agent signings, trades and enough rumors to fill a high school hallway look to make headlines.

The Colorado Rockies will look to improve a roster that has a lot of turnover in just a year’s time. Only 18 players – eight position players and 10 pitchers – remain from the club’s 40-man roster from the end of the 2021 season.

They, along with their competition, will aim to add one or more players in hopes of getting closer to winning the 2023 World Series.

Here are five things to watch during this year’s Winter Meetings:

Hall of Fame gets a little bigger?

On Sunday, Dec 4 at 6pm, the Contemporary Baseball Era Players Committee will announce which of eight players will be inducted into Cooperstown at the Class of 2023 on July 23.

The eight players up for consideration include pitchers Roger Clemens and Curt Schilling, first basemen Fred McGriff, Don Mattingly and Rafael Palmeiro, and outfielders Albert Belle, Barry Bonds and Dale Murphy. 

To be elected, a player needs 75% of votes from the committee. 

The 16-member committee is composed of seven Hall of Fame members, six current major league executives and three veteran media members and historians. Each committee member can vote for up to three players, which means the most names that could possibly be announced is four. 

Murphy is the lone Rockie on this list. Having played with Colorado during the expansion season of 1993 for 26 games before announcing his retirement, Murphy was best known in his career as a member of Atlanta. 

Oct 17, 2021; Cumberland, Georgia, USA; Atlanta Braves former player Dale Murphy throws a ceremonial first pitch before the Braves game against the Los Angeles Dodgers in game two of the 2021 NLCS at Truist Park. Mandatory Credit: Brett Davis-USA TODAY Sports

He was a seven-time All-Star that twice led the National League in home runs, won four Silver Slugger Awards and five Gold Glove Awards, not to mention won back-to-back NL MVPs in 1982-83, something only 13 players have ever accomplished.

MLB Draft Lottery 

In the past, the team with the worst record had the first pick in the following year’s draft. 

It’s now eight weeks out from the end of the 2022 regular season and we still don’t know who has the first pick in the 2023 MLB Draft.

The first ever MLB Draft Lottery will take place on Tuesday, December 6 at 6:30pm.

Picks 1-6 will be determined for the 2023 draft with picks 7-18 going in reverse order of standings for the remaining non-playoff clubs. 

Washington Nationals, Oakland Athletics and Pittsburgh Pirates all have the greatest chance of winning the draft lottery at 16.5%. Cincinnati Reds (13.2%) and Kansas City Royals (10.0%) round out the best five likelihoods. 

The new CBA created the draft lottery in order to disincentivize teams to intentionally lose games for better draft picks. The hope is that this new order of operation will decrease the amount of teams who will fold up shop for a few years, losing nearly 100 games each season, and improve their farm system with a target of having a longer and stronger window of contention a few years down the road.

Colorado finished with the eighth-worst record in MLB at 68-94, so they have a 3.9% chance to earn the first overall selection next year, something it has never held.

The highest the Rockies have ever drafted was 2006 when they selected Greg Reynolds with the second overall pick. Jon Gray (2013) and Brendan Rodgers (2015) were each taken with the third pick and Riley Pint (2016) was selected with the fourth. 

The Scott Boras Show

When he last blessed the Winter Meetings with his presence, he was on the precipice of earning Gerrit Cole and Stephen Strasburg a combined $569 million from the New York Yankees and Nationals, respectively. 

Dec 9, 2019; San Diego, CA, USA; Sports agent Scott Boras speaks to the media during the MLB Winter Meetings at Manchester Grand Hyatt. Mandatory Credit: Orlando Ramirez-USA TODAY Sports

The last time Rockies fans saw him, he was shaking hands with GM Bill Schmidt and manager Bud Black back in March during the press conference to announce Kris Bryant’s seven-year, $182 million pact.

This year, he’ll be working his hardest to sign deals for SS Carlos Correa, SS Xander Bogaerts, LHP Carlos Rodón, RHP Taijuan Walker and 1B Josh Bell, not to mention two players who have been linked to Colorado, OF Brandon Nimmo and OF Cody Bellinger.

Aaron Judge finds his suitor 

To be clear, there is no guarantee Aaron Judge will find a landing spot before everyone packs up and leaves San Diego en masse, but the rest of the baseball world will want that decision to come sooner than later.

Temperatures will have been taken and final offers slid across the table. The Yankees even made a reported eight-year deal worth somewhere near $300 million. 

Oct 4, 2022; Arlington, Texas, USA; New York Yankees right fielder Aaron Judge (99) rounds the bases after hitting home run #62 to break the American League home run record in the first inning against the Texas Rangers at Globe Life Field. Mandatory Credit: Tim Heitman-USA TODAY Sports

Will he return to a Yankees team that desperately needs him? Or will he sign with the San Francisco Giants who may offer a lower salary, but provide more comfort, especially considering he grew up a fan of the club just two hours away in Linden, CA? Maybe a third mystery team will emerge, like perhaps the New York Mets, who just lost out on Jacob deGrom to the Texas Rangers?

Once Judge finds a home, the rest of the pieces can begin to fall into place.

The Rest of the Pieces

Justin Verlander and Carlos Rodón lead this year‘s crop of free agent starting pitchers following deGrom’s five-year, $185 million deal. 

Four premium shortstops are available such as Trea Turner, Dansby Swanson, Bogaerts and Correa. 

Some teams will orchestrate trades to improve their club, while others will look to fill a hole through the Rule 5 draft. 

The first to be held since 2020 and the first following a normal off-season since 2019, the Rule 5 draft allows certain players who have not been placed on the 40-man of their parent club to be selected by another club.

Those eligible need to be placed on the 26-man roster and must remain active for a minimum of 90 days.

Jordan Sheffield (2020) and Tommy Kahnle (2014) are the only Rule 5 picks who have stuck around for a season with the Rockies in their 30-year history. 

Colorado could get creative and draft a player with the eight-overall selection and turn around to trade that player, as they did in 2014 when they took Mark Canha with the second pick from out of the Marlins’ system and trade him to the Oakland Athletics for reliever Austin House.

The Rockies currently have 39 players on their 40-man roster, so there is room to draft and keep or draft and trade.