5 reasons the Winter Meetings will sizzle

Baseball’s Winter Meetings earned their reputation as a bartering bonanza back in those olden days when trades were allegedly constructed on bar napkins and colorful White Sox owner Bill Veeck posted an “Open for Business” sign in a hotel lobby. The Meetings became known for signing sprees when the legendary likes of Dave Winfield, Nolan Ryan and Barry Bonds signed their historic pacts at the annual gathering.

But with polished execs increasingly holed up in their private suites, away from prying eyes, and with so much Hot Stove business conducted over calls, texts and, now, Zooms, there have been quite a few years in which the Winter Meetings transaction wire was no more crowded than your average week of the offseason.

Thankfully, we’ve seen some major Meetings momentum that aligns with the expectations and reputation attached to this anticipated event. The last two Meetings (in 2019 and 2022, both in San Diego) were downright dramatic, with Aaron Judge, Gerrit Cole, Stephen Strasburg, Zack Wheeler, Trea Turner, Xander Bogaerts, Anthony Rendon and Brandon Nimmo all inking nine-figure deals and plenty of other big names coming off the big board.

• Here is one Winter Meetings goal for each team

The Winter Meetings, in other words, are fun again. And as the 2023 installment begins at Nashville’s Gaylord Opryland Resort & Convention Center, we have reason to believe the fun can keep going.

Here’s why:

1. A run of record-breaking signings could continue

It was just a bit before midnight ET (which means it was roughly beer-thirty in San Diego) when Cole and the Yankees agreed to a record-setting pitching pact on the penultimate night of the 2019 Winter Meetings. Cole’s nine-year, $324 million deal destroyed the previous pitching record of seven years, $245 million that had been set by the Nationals’ Strasburg … a day earlier, at the Winter Meetings!

Last year, it was Judge, fresh off the AL single-season home run record, breaking the bank at the Meetings with a nine-year, $360 million agreement with the Yankees that stands as the largest deal ever given to a free agent. (Actually, there had famously been word on social media earlier in the day that “Arson Judge” was close to signing with the Giants, only adding to the drama of the proceedings.)

Now, it might be Shohei Ohtani’s turn to turn the Winter Meetings inside out by setting a new free-agent standard. We don’t know when or where, exactly, the two-way superstar and reigning AL MVP will sign, but we’ve heard he does not intend to drag this important process out very long. If he has any sense of occasion and flair for the dramatic (this is a guy who has hit in the Home Run Derby one night and served as a starting pitcher in the All-Star Game the next, so we think he does), he’ll do so during this Nashville gathering.

• Ohtani rumors: Is a decision coming soon?

2. History could repeat itself in Nashville

A young slugger entering his age-25 season on a Hall of Fame trajectory was put on the trade block by a team paring payroll, and the resulting swap lit up the Winter Meetings.

It happened on Dec. 4, 2007, at -- you guessed it -- the Opryland.

That’s where the Tigers and Marlins agreed to the deal sending Miguel Cabrera to the Motor City, and that could be where the Padres put the finishing touches on a Juan Soto swap.

Soto is a year away from free agency, so he doesn’t come with the two years of contractual control that Cabrera did at the time of that Detroit deal. But Soto is no ordinary one-year rental, having amassed the fifth-highest OPS+ ever for a player through his age-24 season. There has been traction toward a trade, to the point where many executives see it as a foregone conclusion. Padres GM AJ Preller is not one to dilly dally, and the Padres need pitching and clarity on their direction.

If the deal happens, it would be the second Soto deal in the last year and a half. And if it happens at the Meetings, it would be the first blockbuster barter at the event since Giancarlo Stanton went from the Marlins to the Yankees in 2017. (The Yankees, by the way, are in on Soto, so history could potentially repeat itself in multiple ways.)

An Ohtani deal and Soto trade would kick the thin position player free-agent market into gear. The landing spots for Cody Bellinger, Matt Chapman, Jung-Hoo Lee, Teoscar Hernández and others could crystallize quickly once the whereabouts of Ohtani and/or Soto are known.

3. The pitching markets are percolating

We’re not going to see a contract for a full-time pitcher that rivals the Cole deal, of course. But a free-agent market high on both supply and demand has already been initiated by Aaron Nola re-signing with the Phillies and the Cardinals’ aggressive moves for Sonny Gray, Lance Lynn and Kyle Gibson. Even though the arm seen by many as the No. 1 available this winter -- Japanese right-hander Yoshinobu Yamamoto -- will not be meeting with teams until after these Meetings, the other dominoes figure to keep falling. Lefty Jordan Montgomery, fresh off a World Series run with the Rangers, has a lot of interest, and the markets for Eduardo Rodriguez, Lucas Giolito, Marcus Stroman and others don’t figure to be held up by the Yamamoto proceedings.

While signings are cool, trades are cooler (trades have at least twice as many teams involved, so the coolness math here is irrefutable).

Fortunately for us deal devotees, there are several big-name starters on, or potentially on, the block, including the Rays’ Tyler Glasnow, the Brewers’ Corbin Burnes, the Guardians’ Shane Bieber and the White Sox’s Dylan Cease. If any of those arms are dealt this week, it would arguably be the biggest pitching trade at the Winter Meetings since the Sox sent Chris Sale to the Red Sox in 2016.

And with ESPN’s Jeff Passan having reported Friday that the Guardians are open to trading All-Star closer Emmanuel Clase, a relief market fronted by free agent Josh Hader is getting interesting.

4. The Draft Lottery has created new intrigue

A fun new wrinkle of the Winter Meetings is the MLB Draft Lottery, which debuted last year and instantly demonstrated its appeal.

The No. 1 goal of the lottery is to discourage tanking, and already we’ve seen how teams that finish with poor records simply by defeat and not design can benefit from the altered arrangement. The Pirates tied for MLB’s worst record and, therefore, the highest odds of landing the No. 1 pick (which they did, using it to take LSU ace Paul Skenes). But the biggest winner might have been the Rangers, who were clearly trying very hard to win in 2022. They had doled out big dollars on Corey Seager and Marcus Semien going into the season, only to finish with MLB’s seventh-worst record. Thanks to the lottery, they moved up three spots in the Draft, to No. 4, and wound up landing Florida outfielder Wyatt Langford, who was seen by many scouts as worthy of going No. 1 overall in most Drafts.

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Oh, and then the Rangers won the World Series. Pretty good year.

We’ll see who the biggest risers and fallers in the Draft pecking order are when the second Draft Lottery takes place live from the Winter Meetings at 5:30 p.m. ET on Tuesday night on MLB Network.

5. The Rule 5 Draft is not to be ignored

Ever since the 2006 CBA change that reduced the pool of players eligible for the Rule 5 Draft, it’s harder to use this opportunity to go out and get yourself a Johan Santana, as the Twins famously did in 1999.

But two trends contribute to make the Rule 5 as important as ever.

For one, the game is getting younger. Baseball America published a piece last week that showed that the percentage of plate appearances by players aged 24-28 has increased substantially:

Share of PAs by players aged 24-28
1998 to 2002: 41.3%
2003 to 2007: 39.1%
2008 to 2012: 44.6%
2013 to 2017: 44.0%
2018 to 2023: 50.1%

Furthermore, the ever-climbing pitching injury rate -- a product of increasingly high-octane developmental approaches -- creates more opportunities for prospects.

In short, teams are more willing than ever to take chances on unseasoned talent. And the Rule 5 is one avenue to take a low-risk gamble on that kind of player.

Last year, Ryan Noda (A’s), Kevin Kelly (Rays) and Blake Sabol (Giants) joined new teams in the Rule 5 and wound up making what was, by Wins Above Replacement, a positive impact at the Major League level. This year’s crop of available players in Wednesday’s Rule 5 includes two right-handers – C.J. Van Eyk (Blue Jays) and Anthony Hoopii-Tuionetoa (Rangers) who performed well in the Arizona Fall League, and there’s never really any telling what might come out of this process.

Nor is there any telling what might come out of the Winter Meetings. But we’re on a roll. So let’s put up that “Open for Business” sign and have some fun.