Predicting MLB Free-Agent Signings and Trades During 2023 Winter Meetings

Major League Baseball's 2023-24 offseason has already been a little nutty. The Phillies re-signed Aaron Nola for $172 million. Detroit added a couple of veterans in Kenta Maeda and Mark Canha. Atlanta traded for Aaron Bummer. Seattle traded away Eugenio Suárez. St. Louis has already signed not one, not two, but three veteran starting pitchers in Sonny Gray, Lance Lynn and Kyle Gibson. And that's hardly a comprehensive list of the November transactions.

But buckle up, folks.

Winter meetings are coming.

During this four-day window in last year's offseason cycle, Aaron Judge, Trea Turner and Xander Bogaerts signed their contracts at a combined total of just a shade under one billion dollars, Justin Verlander landed with the Mets, Willson Contreras signed with the Cardinals, Cody Bellinger joined the Cubs and about a dozen other noteworthy signings happened during what was a whirlwind of chaos.

That wasn't exactly out of the ordinary, either. There were no winter meetings in 2021 (lockout) and they were conducted virtually in 2020, but the last normal offseason prior to 2022 was when Gerrit Cole, Stephen Strasburg and Anthony Rendon all signed their massive contracts during the 2019 winter meetings.

There will be fireworks this week. And for the sake of all of us in the content producing/consuming business, here's hoping Shohei Ohtani is one of them.

We've got updated predictions for some of the biggest things we expect to transpire by the time all the dust has settled in Nashville on the morning of Dec. 7.

Fear not. We'll get to plenty of predictions on where big-name guys actually sign or get traded.

But let's start out with our bold prediction that we'll end the winter meetings with Japanese ace Yoshinobu Yamamoto as the biggest fish that has not yet been landed.

It wasn't until Yamamoto was officially posted by the Orix Buffaloes two weeks ago that he was allowed to start negotiating with MLB teams. But what's most intriguing about Yamamoto is that he is one of the few free agents with a concrete deadline. If he doesn't sign with a team by Jan. 4, the window closes and he stays with the Buffaloes.

You might think that means he'd be in even more of a rush to get a deal done during winter meetings, but the ball is really in his court to see how desperate teams get for him as both that clock ticks down and the pool of options runs dry when the other marquee starting pitchers get snatched up.

Aaron Nola and Sonny Gray are already gone. Chances are both Blake Snell and Jordan Montgomery will come off the board in the next few days, which would leave this 25-year-old as the clear-cut best pitcher available, if he isn't already. And at that point, the bidding war could get out of hand.

Last year, Kodai Senga waited until a couple days after winter meetings to sign his five-year, $75 million deal with the Mets, somewhat surprisingly getting the fourth-largest sum of guaranteed money among the available starting pitchers. And if Yamamoto waits at least until Shohei Ohtani makes his foundation-of-the-sport-altering decision, there should be several teams pivoting and upping their original offers to drive the price well north of $200 million.

For more than a full calendar year, I've been steadfast in saying Shohei Ohtani is most likely going to end up with the Dodgers.

Had the Angels been willing to trade Ohtani either last offseason or ahead of the August 1 deadline, the other Los Angeles team was the one best suited to give the Halos the necessary prospects to make a swap happen. And it was clear from their financial approach to last offseason that the Dodgers were positioning themselves to hand the generational superstar a blank check.

This week, at long last, it finally happens.

How much it will cost to land Ohtani is still anyone's guess, although most of those guesses seem to be groupthinking their way to around $520 million. That's exactly where I had him projected in mid-June, though we assumed at that time he would be pitching in 2024. Projected contract figures for Ohtani never seemed to change in the slightest to account for his second major elbow surgery, and something below half a billion might be a little more realistic.

But whether it's $400 million or $600 million, the Dodgers are going to make Ohtani tell them no, and then they will offer a little more on top of that.

There's been plenty of speculation about the Giants, Rangers, Cubs and even the Blue Jays as we await the earth-shattering news. But the Dodgers have long been the favorite here, and they'll get their man.

Given how good Cody Bellinger was this season, how much better he was in winning the 2019 NL MVP and that he's only 28 years old, it's understandable why his is the second-most coveted bat (behind Shohei Ohtani, of course) this offseason.

But given how uninspiring his play was from 2020-22, it's understandable why a lot of fans are torn on whether they even want their team to win the Bellinger Sweepstakes, regardless of what the final cost ends up being.

Bellinger is going to get nine figures, though. And considering the scarcity of bats available in free agency this year, the first of those nine figures just might be a two.

That would shock a lot of people—including myself, if we're being honest—but let's not forget we are one year removed from both Trea Turner (11 years, $300 million) and Xander Bogaerts (11 years, $280 million) signing for considerably more/longer than anyone was reasonably anticipating.

Instead of a five-year, $120 million deal ($24 million AAV), it's plausible Bellinger gets a 10-year, $200 million deal ($20 million AAV). But for every dollar over $100 million Bellinger receives one year after getting non-tendered by the Dodgers, the shock value of that breaking news also increases.

One caveat here: If Juan Soto gets traded to the Yankees before Bellinger signs, that changes the market entirely. The Yankees and Giants are the two most logical landing spots for Bellinger, and they could get into quite the bidding war, keeping in mind it was primarily those two teams sparring over Aaron Judge last year. But if the Yankees get Soto first, the desperation overpay for Bellinger becomes less likely to happen.

There are four big-name starting pitchers allegedly on the trade block: Cleveland's Shane Bieber, Milwaukee's Corbin Burnes, Tampa Bay's Tyler Glasnow and Dylan Cease of the White Sox.

And Atlanta is very much interested in trading for a starting pitcher.

Of the four, Bieber and Cease seem like the best candidates for the Braves, with the Cease connection gaining a lot of traction recently.

Cease still has two years remaining until free agency, which arguably makes him more attractive as a trade target than the other three who will hit free agency in 11 months. Moreover, he was born and raised in the greater Atlanta area, and MLB Insider Jon Morosi tweeted on Thursday that trade talks "have intensified" in recent days and that Atlanta is "among the finalists" to land Cease.

But doesn't trading for Bieber and immediately signing him to a team-friendly extension seem like the ultimate Atlanta thing to do?

Bieber was injured for a chunk of this past season, and his entire pitching arsenal has grown more hittable with each year since he won the AL Cy Young in 2020. But he's still pretty darn good and is only 28 years old.

It would just be sooo Alex Anthopoulos to trade for Bieber, extend him for five years at maybe 60 percent of the price Jordan Montgomery will fetch in free agency and then have him average 4.0 or more WAR over the life of the deal.

Blake Snell is most certainly not going to the Rockies and almost definitely not ending up with the Diamondbacks. But between the Dodgers, Giants and Padres, someone in the NL West is going to sign the 2023 NL Cy Young winner during the winter meetings.

Of those three, San Diego is the biggest long shot. But as the Juan Soto trade rumors continue to get louder by the day, why couldn't the Padres re-sign Snell? We've all heard they want to get their payroll under $200 million in 2024, but they do still want to try to win the World Series. Trading Soto and signing Snell would give them a chance to accomplish both of those goals.

With all sorts of money to spend, the Dodgers are a strong candidate to land any noteworthy free agent, especially any starting pitcher, given the current injury-laden state of their rotation. They should get Shohei Ohtani, but they might get Snell, too.

The Giants sure seem like the favorite, though.

Snell has pitched extremely well in the homer-averse confines of Oracle Park in his career, and the Giants are desperate to make some sort of big splash after coming away from last year's winter meetings with little more than a bunch of swings and misses. Both the Barry Zito and Johnny Cueto nine-figure deals kind of blew up in their face, but they are ready and willing to be hurt by a tantalizing pitcher once again.

There are a lot of pitchers who could get traded this week, but the lone near certainty to be on the move at some point this offseason is Tampa Bay's Tyler Glasnow.

From the moment the Rays signed Glasnow to the two-year deal in which the salary for year No. 2 ($25 million) is nearly quintuple the first year ($5.35 million), it was always likely they would trade him away this offseason, as I don't believe they have ever paid anyone a salary over $15 million.

Two questions linger in a possible Glasnow deal, with the obvious first one being: Where does he land?

Nearly every MLB team is in the market for starting pitching, but $25 million for one year of a guy who has yet to log more than 120 innings in a season in his eight-year career is quite the expensive gamble. If he does manage to stay healthy, though, Glasnow has a 3.03 ERA, a 1.01 WHIP and a 12.5 K/9 dating back to the start of 2019 and could be a Cy Young candidate.

The Dodgers are probably most likely to make that gamble, but the Cubs and Yankees will also be in the mix, with the Reds looming as an intriguing dark horse. (Our official prediction is the Dodgers, who would clearly be in the market for a one-year stopgap starter if they do get Ohtani.)

The other question is: Are the Rays kind of going to punt away the 2024 season?

It was after six consecutive winning seasons from 2008-13 that they previously had little choice but to slog through a bit of a rebuild, and they are once again in a tough spot after six straight solid years.

Shane McClanahan, Jeffrey Springs and Drew Rasmussen are each recovering from major elbow surgery and will likely all be out until at least the All-Star break, if not the entire season. So if they were to trade away Glasnow, the rotation gets questionable in a hurry, with a lot riding on then-projected No. 3 starter Shane Baz, who has pitched all of 40.1 innings in his MLB career and is coming back from a Tommy John surgery of his own.

Throw in the uncertainty surrounding Wander Franco and the notion that the AL East might be even more loaded in 2024 than it already was in 2023, and it wouldn't be that surprising if the Rays trade away more than just Glasnow.

It wouldn't be a full-blown, Oakland A's-level tank job by any means. Much more of a "retooling for a more plausible run in 2025" situation. But if they're embracing some salary dump, might as well look to move Manuel Margot and Brandon Lowe, too—possibly even packaged in the Glasnow trade to increase the haul that they get for moving the potential ace.

Last year, the Texas Rangers pulled off the biggest surprise of the offseason, inking Jacob deGrom to a five-year, $185 million deal a couple of days before the winter meetings began.

That bombshell dropped one year after they committed half a billion dollars to Corey Seager ($325 million) and Marcus Semien ($175 million).

And there's a good chance the reigning champs go back to that well again this week to improve their odds of becoming the first repeat champs in nearly a quarter century.

The Rangers are perhaps one of the teams still in the running for Shohei Ohtani, but that one is a longshot.

It's much more likely they'll either re-sign Jordan Montgomery for somewhere around $150 million or make Josh Hader the highest-paid reliever in the majors at something in the vicinity of $110 million.

Of the two, Hader would solve the much bigger problem. Bringing back Montgomery would be swell, given what a massive role he played in that World Series run. However, they already have Max Scherzer, Nathan Eovaldi, Jon Gray, Andrew Heaney, Dane Dunning, possibly deGrom by the end of the year and several intriguing, probably MLB-ready prospects waiting for their chance to shine. They don't need another starter.

Texas' bullpen is in considerably less great shape, though, even if both Jose Leclerc and Josh Sborz can continue to pitch as well as they did in October. Signing Hader would emphatically address what is frankly the only real concern about the Rangers in their title defense.

They'll get one of the two, though, because they aren't going to rest on their laurels after winning the first World Series in franchise history.

It won't quite rival the "Arson Judge" calamity from last offseason, but the Juan Soto trade rumors have already been a monthlong, slow-burning fire, waiting to erupt like a volcano.

And when "Childish Bambino" ends up on the move during the winter meetings—most likely to the New York Yankees, though he does have plenty of other motivated suitors—it will be a seismic moment.

The dream, internet-breaking scenario here would be, of course, a three-team swap.

What exactly that would look like, who knows?

Maybe the Mariners swoop in on talks with the Padres and Yankees, resulting in (among other moving parts) Soto going to the Bronx Bombers, Seattle shipping a young pitcher to the Padres and the M's getting Jasson Domínguez?

Or perhaps a three-teamer could be where we finally see Gleyber Torres on the move after more than a year of him being in trade rumors? It's hard to imagine the Red Sox working out a trade with the Yankees or the Dodgers and Padres partaking in civil trade conversations, but Torres would fit well with either Boston or Los Angeles in 2024. (Seattle certainly could also use a Torres-sized upgrade at second base.)

Even if it's a much less complicated two-team trade, though, it's going to be a huge domino.

As previously mentioned, a Soto trade could have a major impact on the Cody Bellinger market if the swap happens before the signing. Same goes for corner outfielders Lourdes Gurriel Jr. and Teoscar Hernández, who are arguably top-five bats in this year's free-agency cycle lacking for quality hitters.