In the MLB world, December tends to be the month of big, fancy, splashy free agent deals. This year figures to be the same as just a pair of our Top 20 Free Agents have inked deals thus far. That should all change soon.

The MLB Winter Meetings begin this Sunday where every team, GM, and agent will meet throughout the week in Dallas, Texas. We’re all waiting for things to truly great rolling, so let’s take a look at how the next week may shake out around the baseball world.

Just Baseball Trivia of the Week

Our newsletter will have a trivia question every week to test and expand the baseball knowledge of our subscribers! The answer to the weekly trivia question will be at the bottom of the newsletter each week.

Who held the record for the largest MLB contract ever in terms of total value prior to 2018?

A) Manny Machado

B) Derek Jeter

C) Alex Rodriguez

D) Barry Bonds

Winter Meetings Begin Sunday

Every year, the Winter Meetings represent a time where the landscape of the league can drastically shift. Not just free agent deals, but also blockbuster trades, extensions, and more are made during the week of the meetings compared to any other time throughout the winter.

So with these prodigious meetings starting Monday, we’re here to provide a preview of what could take place over the next week.

Done Deals

While the market had been quiet up to this point, a few big names are off the board with the biggest one heading to…*drumroll*…the Los Angeles Dodgers. Not many have signed, but the ones that have may signal that’s coming.

• Two-time Cy Young Award winner Blake Snell signed a five-year, $182 million deal with the Los Angeles Dodgers to become another star in the rotation for the defending champions. Snell was possibly the best pitcher in baseball in the 2nd half of the year with San Francisco and broke the news he was joining the Dodgers in a way that felt very on-brand.

• But it was actually the Angels that ignited the offseason first, as they signed veteran left-hander Yusei Kikuchi to a three-year, $63 million contract. He shined after a deadline trade to Houston with a 2.70 ERA across his 10 starts with the Astros and the Angels made him a priority.

• Expected to be a huge spender this winter, the Mets began by signing starter Frankie Montas to a two-year, $34 million deal. Meanwhile, the Cubs brought in a different left-hander in veteran Matthew Boyd on a two-year, $29 million deal after he impressed in 12 games (four in the postseason) with Cleveland coming off Tommy John Surgery.

• There’s been one notable trade thus far as well, with the Reds and Royals striking a deal that sent Brady Singer to Cincinnati with Jonathan India and Joey Wiemer heading back to Kansas City.

• The Dodgers didn’t just sign a top arm as they also gave a five-year, $74 million extension to NLCS hero Tommy Edman, who will continue to be a key versatile offensive piece for them.

• Boston is expected to be active this winter and they got started by adding veteran reliever Aroldis Chapman on a one-year, $10.75 million deal. He may not be his peak self anymore, but the 36-year-old still struck out 98 batters across 61.2 innings in 2024.

• In a market without any great positional options, Kyle Higashioka may have been the best catcher available after hitting 17 home runs with San Diego in 2024. The Rangers agreed to a two-year, $12.5 million deal that also contains a third year mutual option with the veteran catcher.

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Top Names Ready to Sign

All eyes are on Juan Soto as the soon-to-be second-highest paid free agent ever seems likely to sign in the near future. The Yankees remain the favorites to sign him, but they’ll have to pivot quickly if he signs with the crosstown Mets, rival Red Sox, or loaded Dodgers.

With Snell off the market, the pitching side of free agency hinges largely on Corbin Burnes and Max Fried. With Snell signing a deal worth over $35 million AAV, the price for those two should increase with plenty of teams as potential suitors.

No top free agent bat has signed yet as many big spenders await a Soto decision, but there are some logical fits for a number of the top hitters available. Here are some teams that will targeting each of these top hitters:

Most of the biggest aforementioned teams in free agency are focused on Soto while others like Philadelphia, Atlanta, San Diego, and more will take different — but not necessarily low-cost — routes towards improvement. A few small market teams such as Kansas City and Detroit are ready to improve as well after exciting surprise playoff appearances.

Trade Candidates

Plenty of names will fly around the rumor mill as some teams will pivot from solely focusing on free agency to acquiring (or moving) talent via trades.

Signing players to huge contracts always comes with some degree of risk, which can ultimately lead to such players being shopped eventually. These five players including eight-time All-Star Nolan Arenado could be shopped as a result this winter and plenty of suitors to boot.

The top arm that’s certainly on the market is White Sox ace Garrett Crochet, and these five mock trades could potentially get a deal done to send the left-hander to a team trying to contend in 2025.

Many other names will be floated in trade talks and there are always deals made that aren’t necessarily expected prior to December. Buckle up because it’s time for the best part of the offseason!

Other Headlines

• MLB Commissioner Rob Manfred shared the idea of “Golden At-Bat Rule” that would allow a team to choose one at-bat per game to use a hitter of choice, regardless of where they currently are in the lineup. This idea supposedly had a lot of buzz at the owners meetings this year.

• Giants legend Brandon Crawford announced his retirement last week. He won two championships as the shortstop of his hometown team in 2012 and 2014 in addition to being a three-time All-Star and four-time Gold Glove Award winner.

Trivia Answer: C) Alex Rodriguez

After opting out of the final three years of his prior contract after the 2007 season, “A-Rod” signed a 10 year, $275 deal to remain with the Yankees for the rest of his career. It was the largest contract in MLB history for quite some time until Manny Machado broke that record after the 2018 season.

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