7 storylines to watch as Winter Meetings unfold

It’s the most wonderful time of the year.

No, we’re not talking about the holiday season -- though that’s pretty great, too -- but rather baseball’s Winter Meetings, which are underway following a two-year hiatus for the offseason’s marquee event.

Executives and agents alike began laying the groundwork for potential deals last month at the General Managers Meetings in Las Vegas, but the entire baseball world has descended upon the Manchester Grand Hyatt in downtown San Diego with the goal of closing deals as all 30 clubs look toward the 2023 season.

What will we be talking about all week? Here are seven storylines to watch.

99 problems

If there’s anybody in the baseball world who doesn’t have any problems this winter, it’s Aaron Judge. The reigning American League Most Valuable Player is looking at a titanic payday, though the $300 million question is which team will be writing the checks?

The Yankees -- whose most recent offer to Judge was for eight years and nearly $300 million -- remain the favorites to retain the slugger, though the Giants are still contenders to land Judge. Aside from those two clubs, the Dodgers are a team to watch, while the popular “mystery team” is always a possible twist to this saga.

Many industry insiders believe Judge will sign during the Winter Meetings, which would open up the free-agent market for some of the other top players.

• These are the FAs most likely to sign at Winter Meetings​

Editor's note: Trea Turner has agreed to an 11-year, $300 million deal with the Phillies, according to a source. The club has not confirmed.

Pulling out all the (short)stops

For the second consecutive offseason, the shortstop market is robust with superstar talent. Trea Turner, Carlos Correa (who was a free agent last year, too), Xander Bogaerts and Dansby Swanson are all available, though far more than four clubs are in the mix to sign one of the All-Stars.

Turner has been connected to the Phillies for weeks, while the Twins are hopeful to bring Correa back on a new long-term deal. The markets for Bogaerts and Swanson appear to be broad, though new suitors could emerge based on other signings.

It would be surprising if at least one of the shortstops didn’t sign during the Winter Meetings, and once the first domino falls, the others could follow suit quickly.

• Rumors: Bogaerts | Correa | Swanson | Turner

Agent of change

There was a time not too long ago when it felt like Scott Boras slow-played the majority of his free-agent clients, often taking them into January and February -- and in some extreme cases, well into Spring Training -- before landing deals.

One of the most famous instances came after the 2018 season when Bryce Harper remained on the open market until March 2, 2019, before signing his 13-year, $330 million deal with the Phillies.

The following winter, Boras had three of the top free agents of the offseason: Gerrit Cole, Stephen Strasburg and Anthony Rendon. As the Winter Meetings arrived, the baseball world was longing for some serious free-agent action -- and Boras delivered.

Strasburg signed that Monday, Cole agreed on Tuesday and Rendon agreed on Wednesday, a trifecta that totaled $814 million in contracts during one of the most eventful Meetings in years. Will we have a similar flurry of signings this week?

Boras’ free agents include Correa, Bogaerts, Carlos Rodón, Brandon Nimmo, Cody Bellinger, Michael Conforto, Taijuan Walker and Josh Bell, so it will be fascinating to see whether the agent attacks the market the way he did three years ago -- the last time the Meetings were held in person.

Editor's note_: _With the Winter Meetings underway in San Diego, Justin Verlander has agreed to a two-year, $86 million deal with a vesting option for a third year with the Mets, according to a source. The club has not confirmed.

This is 40

Now that Jacob deGrom has signed with the Rangers for five years and $185 million, all eyes will be on Justin Verlander, the reigning American League Cy Young Award winner who turns 40 in February.

Verlander is said to be seeking at least $40 million per season over two years, following the model set by former teammate Max Scherzer (three years, $130 million) last year. The Astros appear willing to let Verlander sign elsewhere, leaving the Dodgers as front-runners. The Mets have also spoken with him as they prepared for the possibility of deGrom leaving town.

While Verlander will garner plenty of attention at the Meetings, Rodón and Kodai Senga are also generating significant interest, while Chris Bassitt and Jameson Taillon are viewed by most as the two best starters beyond those three.

Trade show

One of the biggest attractions at the Winter Meetings is the annual Trade Show, where vendors look to peddle their products to a variety of potential clients.

In the baseball world, the trade show has an entirely different meaning. In addition to free agency, teams can work to improve their rosters for next season -- or with an eye toward the future -- via the trade market, and this year, a pair of teams with catching to deal will be of particular interest.

The Athletics have one of the more appealing trade chips in Sean Murphy, a Gold Glove catcher entering his age-28 season. Murphy is under club control through 2025, but Oakland has Shea Langeliers, one of the centerpieces of last year’s deal that sent Matt Olson to the Braves, waiting in the wings.

Another team with catching depth from which to trade is the Blue Jays, who have the trio of Alejandro Kirk, Danny Jansen and Gabriel Moreno. Toronto has been getting calls on its catchers for months, but it would be somewhat surprising for the club not to deal one of them this offseason to address another area of need.

Free agents Willson Contreras and Christian Vázquez are also options for clubs in search of catching help.

• Winter Meetings predictions

If not Judge, then who?

Judge is the clear-cut No. 1 player on the free-agent market, but for those clubs in search of outfield help that aren’t willing to hand out a $300 million contract, there are a number of options.

Nimmo is seen as the next-best option thanks to his elite on-base skills, solid defense and all-around game. Mitch Haniger’s talent has never been in question, but his injury history could be a concern to some teams. Andrew Benintendi posted an All-Star first half before injury cut his season short, but he should be in line for a solid deal. Conforto hasn’t played since 2021, but the interest in him seems broad, so he could sign a multi-year deal.

Bottom line: There is no free-agent outfielder that compares with Judge, but there are myriad players who will be solid additions.

Big spenders?

The usual suspects will be attached to many of the top free agents, so expect to hear the Yankees, Dodgers, Mets, Giants and other big-market clubs mentioned as potential landing spots for a number of players.

The surprise team to watch? The Orioles. Baltimore’s 83-win season has the club thinking about the postseason in 2023, and given that the O’s haven’t signed a free agent to a multi-year deal since 2018, GM Mike Elias should be quite active this week.

The Orioles, who appear to have a deal in place with veteran righty Kyle Gibson, are looking to add one or two starting pitchers and another bat or two. Even if they don’t play at the very top of the market, there are a number of solid players in the second and third tier of free agents to make an impact on the young, emerging club.