MLB free agency predictions entering the Winter Meetings: Who signs, who waits and why

The MLB Winter Meetings are in a matter of days. For those unfamiliar, the Winter Meetings are an offseason pillar – arguably its main focus – in which agents, players, teams and even reporters reside in the same hotel for half a week to meet face to face.

Zoom meetings and phone calls can only help so much. Sometimes, the parties involved must meet in person. For the likes of Kyle Tucker, Kyle Schwarber, Cody Bellinger and a slew of international stars from NPB, this week could make (or cost) them millions of dollars.

When are the MLB Winter Meetings, and why are they so important?

The MLB Winter Meetings are complete chaos. Don't believe me? Just ask FanSided's resident MLB Insider, Robert Murray. The man is running around, wining and dining with agents, executives and other insiders all the while providing us with the latest insight. On the coverage end, it's exhausting. For those directly in the fray, it's exhilarating.

The Winter Meetings technically begin on Monday, Dec. 8 and end on Dec. 11. In recent years, the media circus surrounding this event has only grown, as a large number of players will choose their next steps in Orlando next week. As it pertains to free agents specifically, the rumors and rumblings are endless, and only just beginning. Just look at this list of MLB stars available this winter, and you'll get why it's such a big deal.

This list does not include international stars like Tatsuya Imai, Munetaka Murakami and Kazuma Okamoto, all of whom have entered the free-agent market and could meet with teams in Orlando this week.

The best free agents who could sign at the MLB Winter Meetings

Kyle Schwarber

When it comes to the top of the free-agent market, Kyle Schwarber is moving fast. Schwarber has every reason to sign soon, as he is the only player available who hit 50 home runs last season and is primarily a DH. The longer Schwarber waits, the more his value could decrease – and that'll never be more evident than at the Winter Meetings. Schwarber is favored to remain with the Philadelphia Phillies, as he is beloved at Citizens Bank Park. His power plays well there, and the Phillies want to keep him around. However, the longer he waits, the more he and his agency risks the Phillies pursuing a backup plan. No one should want that.

Verdict: Schwarber re-signs with the Phillies

Cody Bellinger

I'm going out on a limb with Bellinger, who is one of the best outfielders available and has been linked to both New York teams, among others. However, Bellinger has a lot to gain by signing as early as possible at the Winter Meetings. It is Bellinger, not Kyle Tucker, who could set the outfield market in Orlando. Bellinger can play center field, either of the corner outfield spots and first base. He'll be highly-coveted this winter for his bat as well. As much as the Yankees may want to pursue Kyle Tucker, expect them to move on Bellinger early and make him an offer he can't refuse far before Tucker finally agrees on his megadeal.

Verdict: Yankees bring back Cody Bellinger

Framber Valdez

Dylan Cease was the first high-profile starting pitcher to go this winter, signing a seven-year, $210 million deal with the Toronto Blue Jays. Cease was connected to several other contenders, including the Cubs and Mets, both of whom are in need of starting pitching. Considering Valdez was expected to receive an even higher AAV than Cease, his market should move quickly at the Winter Meetings. A team like the Mets, which desperately needs rotation help, can't afford to wait around.

Verdict: Framber Valdez signs with the Mets

Edwin Diaz

The New York Mets signed Devin Williams as their closer-in-waiting should Edwin Diaz, their beloved closer of seven seasons, find another suitor. With the relief market moving quicker than any pundits expected this winter, don't be surprised if Diaz is one of the biggest names taken off the board in Orlando. As much as the Mets would like to keep him around, even Steve Cohen can run out of money, and New York is chasing many of the top free agents already. A team like the Dodgers – built to win now but in need of back-end bullpen help – could easily sweep Diaz off his feet.

Verdict: Edwin Diaz signs with the Los Angeles Dodgers

Which free agents will benefit from waiting to sign after the Winter Meetings

Kyle Tucker

I'd put money on Kyle Tucker waiting out the winter meetings, rather than signing before anyone expected. Tucker may be quiet, but even he understands the benefit of allowing, say, Cody Bellinger to sign before he does. Tucker's agent, Casey Close, is said to be seeking a $400 million deal for his client, if not more. Tucker is easily the most-accomplished offensive player in this class. There's little reason for him to agree to a deal before he has to, and if Bellinger signs a lucrative deal in Orlando, Tucker's price tag will only increase.

Verdict: Kyle Tucker waits for his $400 million deal

Alex Bregman

We've been here before with Alex Bregman and Scott Boras, no? Bregman wants to return to the Boston Red Sox, but rumor out of Beantown is that Craig Breslow wants to avoid another luxury tax penalty. That gives him about $21 million to play with, which means these two sides will play hardball. Expect Boras to collect lucrative offers for his top client at the Winter Meetings, but avoid signing before Boston has a chance to counter.

Verdict: Alex Bregman is willing to wait on the Red Sox

Pete Alonso

If Schwarber really does sign at the Winter Meetings (or sooner), it will benefit Pete Alonso and Scott Boras to wait things out. Alonso doesn't offer as much power as Schwarber, but he is also younger and still productive enough defensively that he won't be shoehorned as a designated hitter alone. Alonso has said he is open to playing DH, which should help him land a long-term deal. As for potential suitors, he remains an option for the Mets, and a possible backup plan for the Phillies, among other contenders. Alonso's market is wide open, and it should remain that way past this week.

Verdict: Pete Alonso will let Kyle Schwarber set the market

NPB stars like Tatsuya Imai, Munetaka Murakami and Kazuma Okamoto

This may be the first slew of Japanese stars in quite some time who weren't immediately linked to the Los Angeles Dodgers. Considering the uncertainty that comes with a transition from NPB to MLB, the likes of Imai, Murakami and Okamoto won't immediately set their market. In fact, they were just posted, and their agents are finally making the rounds. Many of those conversations around contract terms and realistic expectations will take place at the Winter Meetings, as they typically do.

Verdict: A wait-and-see approach for these NPB stars