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The five biggest questions as baseball’s Winter Meetings heat up

As we wait for the first big domino to fall, here’s what to look for during the busiest period of baseball’s offseason.

Shohei Ohtani of the Los Angeles Angels looks on during a game against the New York Yankees at Angel Stadium of Anaheim on July 19, 2023 in Anaheim, California. Photo by Sean M. Haffey/Getty Images

The 2023 MLB Winter Meetings are officially underway, and although we’ve had just one major trade so far, the rumor mill is already working overtime. With plenty of big names available either via free agency or trade — including quite possibly the biggest name in the history of the sport — what is annually the busiest stretch of baseball’s offseason figures to be even busier this year.

So what can the baseball world expect from the next few days in Nashville? We’ve compiled the following handy guide, organized in the form of five (or more) burning questions we could get the answers to.

1. Will Shohei Ohtani find a new home?

Let’s start with the obvious. Ohtani’s free agency isn’t just the biggest story of the winter. It’s one of the biggest stories in MLB history, a two-time American League MVP and two-way unicorn who’s still just 28 and also happens to be the best and most famous player in the world. His unprecedented excellence and star power mean he’s going to sign the largest contract in MLB history, whether that’s in excess of $500 million or $600 million — and despite not being able to take the mound again until 2025.

Where might he end up? Ohtani and agent Nez Balelo have done a great job of keeping things close to the vest so far, but it’s safe to say that they’re looking to land with a contender after years of mediocrity with the Angels. The Dodgers and Giants seem like frontrunners right now, with the Mets, Yankees, Rangers and other big-market clubs cooling off a bit of late, but keep an eye on someone like the Blue Jays, Cubs, Mets or Braves to swoop in.

2. Will the big international free agents sign?

What would otherwise be a somewhat uninspiring crop of non-Ohtani domestic free agents is buoyed by some incoming stars from both Japan and Korea. The headliner here is 25-year-old Japanese righty Yoshinobu Yamamoto, whose age and ace upside have him in high demand — and could lead to a contract north of $200 million. Countryman (and WBC teammate) Shota Imanaga doesn’t have quite the same ceiling, but the veteran lefty should also have a robust market among contenders looking for pitching (read: all of them).

There’s also Korean outfielder Jung Hoo Lee, who doesn’t bring much in the way of power but has elite bat-to-ball skills and plays a very good center field — think a younger Andrew Benintendi, a player that would fit an awful lot of teams right now.

By way of reminder, teams in both NPB and KBO that post players for MLB consideration are entitled to a “posting fee” if those players sign with a big-league team. Here’s how that system presently works:

Contract worth less than $25 million: 20% of contract value

Contract worth $25 million to $50 million: $5 million plus 17.5% of amount over $25 million

Contract worth more than $50 million: $9.275 million plus 15% of amount over $50 million

Yamamoto, Imanaga and Lee all figure to clear $50 million in total contract value.

3. What about the other big stateside free agents?

Notably, we saw two premium free agents — Aaron Nola (Phillies) and Sonny Gray (Cardinals — go off the board before we even got to December. That ups the urgency even more at these Winter Meetings, and is cause to suspect that things could move quickly in Nashville — especially in a starting pitching market whose top tier is now down to just Yamamoto and Blake Snell. In addition to Ohtani and Yamamoto, seven of our top 10 free agents remain available:

No. 3 Cody Bellinger, OF/1B
No. 5 Blake Snell, SP
No. 6 Matt Chapman, 3B
No. 7 Eduardo Rodriguez, SP
No. 8 Jordan Montgomery, SP
No. 9 Marcus Stroman, SP
No. 10 Clayton Kershaw, SP

That’s a lot of headline-grabbers, and some of them will surely, you know, grab headlines before the party in Nashville breaks up. Given the activity we’ve already seen on the starting-pitching front, some of those arms could be snatched up very soon.

4. Will the Yankees swing a deal with the Padres for Juan Soto?

The Padres, after running one of the largest payrolls in MLB last season, are said to be looking to shed significant salary ahead of 2024. The easiest way to do that? Deal star outfielder Juan Soto, who’s in line for upwards of $30 million in arbitration in his final year before hitting free agency. The Yankees aren’t hurting for money, and they just so happen to need 1) a corner outfielder and 2) a middle-of-the-order lefty bat to pair with Aaron Judge. Plus, GM Brian Cashman has plenty of young pitching depth to deal from, making them the presumptive frontrunners for Soto — whom all signs point to being very, very available.

While Soto’s 2024 salary and impending free agency figure to limit his market, New York won’t be the only team trying to get a trade done. The Blue Jays have money to spend, a need in left field and a bad taste in their mouths after last season’s Wild Card sweep, while a team like the Mariners or Giants could also swoop in.

5. Will any other blockbuster trades go down?

On the non-Soto trade front, things are also plenty active. Specifically, a number of frontline starting pitchers may be available in trade, from Dylan Cease of the White Sox (the hometown Braves have been heavily linked), Corbin Burnes of the Brewers, Tyler Glasnow of the Rays and Shane Bieber of the Guardians. If you want to get really crazy, it’s not out of he question that new Mets president David Stearns could pull the trigger on a Pete Alonso deal, and there’s been some smoke about Toronto hitting the reset button by trading star shortstop Bo Bichette. While those still feel a bit farfetched, expect a ton of arms to be swapping teams — and other position players like Rays outfielder Randy Arozarena, Red Sox outfielder Alex Verdugo, Brewers infielder Willy Adames and Twins veterans Jorge Polanco and Max Kepler as well. Buckle up.