MLB Insider: Juan Soto, Alex Bregman and 5 bold predictions for the Winter Meetings

The Major League Baseball offseason is a few weeks old, and there has been some movement. Jorge Soler, Travis d’Arnaud, Yusei Kikuchi and Kyle Hendricks are Los Angeles Angels while Brady Singer was traded to the Cincinnati Reds in a deal that sent Jonathan India and Joey Wiemer to the Kansas City Royals.

But the bulk of the offseason activity remains and the Winter Meetings in Dallas, Texas from Dec. 8-12 should lead to a flurry of activity with Juan Soto, Alex Bregman, Corbin Burnes, Willy Adames, Max Fried and Blake Snell looming on the market.

Here’s a few bold predictions for the Winter Meetings.

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Juan Soto signs at the Winter Meetings

The feeling around baseball is that Soto’s agent, Scott Boras, will sign just before or at the Winter Meetings.

Soto and Boras have met with the leadership groups of the New York Yankees, New York Mets, Toronto Blue Jays, Boston Red Sox, Philadelphia Phillies and Los Angeles Dodgers. The meetings were a “get to know each other” type setting that led to no offers. But offers are expected to be extended starting this week, according to ESPN, which lends credence to the thought that Soto could sign during the Winter Meetings from December 8-12.

And if Soto does indeed sign during the Winter Meetings, one thing is certain: all hell would begin to break loose.

The Winter Meetings will be extremely active

Last year’s Winter Meetings were dull and what made everyone in baseball realize we were in for a very, very slow offseason.

This year, I expect the Winter Meetings to be very active. I expect Soto to come off the board and perhaps multiple other top players to find new homes. I also expect the mid and lower-tier markets to see some action as well. I think, based on the seriousness that teams are indicating early this winter, this will end up being one of the most active Winter Meetings in recent memory.

The Boston Red Sox make a big splash

I don’t know what it will be, but I expect the Red Sox to make a big splash.

This could very well be an offseason prediction – I’m not sure when the Red Sox’s splash will ultimately come – but I expect them to make a splash. There’s just too much smoke to ignore and, quite frankly, with how the Red Sox have indicated that they’ll spend, anything less than adding a star or two will seem like a failure to the fanbase.

The Red Sox have been connected to Juan Soto, but signing the superstar outfielder away from the Mets or Yankees could prove very difficult. The Red Sox have been connected to the upper level free-agent starting pitchers and could sign one while trading for a player like Garrett Crochet. Willy Adames, the Milwaukee Brewers’ star shortstop, is another possibility.

The options are endless for the Red Sox and I expect their roster to be significantly improved this offseason, perhaps as early as the Winter Meetings.

Jack Flaherty signs a $100+ million contract

In polling different executives and agents around baseball, the feeling I get is that it’s entirely possible that Jack Flaherty signs a contract worth over $100 million.

It’s unclear what team will give Flaherty that contract – it’s unlikely that the Dodgers would do that – but the right-hander is in position to cash in this offseason. After all, he was much improved with the Detroit Tigers, and continued that surge with the Dodgers and finished the season with a 3.17 ERA and 194 strikeouts in 28 starts.

Flaherty is in position to sign the fourth largest contract for a free-agent starter this offseason behind Max Fried, Blake Snell and Corbin Burnes.

Alex Bregman goes to Tigers and reunites with AJ Hinch

I want to make it clear that I have no information to back this up. This is strictly a guess based on pure vibes.

But it makes sense. The Detroit Tigers are much improved under manager AJ Hinch and appear primed to be a consistent contender in the American League Central. They have a young roster and the financial flexibility to sign a star, and considering Alex Bregman’s connection to Hinch – the two were together with the Houston Astros – a Bregman-to-Detroit signing makes plenty of sense.

The Astros, however, have made it clear that Bregman is their top priority. They have had “productive” conversations with his agent, Scott Boras, and feel good about their chances of retaining the star infielder. But if the two sides fail to agree to terms, it wouldn’t be a surprise if the Tigers swooped in to sign Bregman.