We’re more than two weeks into MLB free agency, and not one major deal has been struck. That means the action is coming. 

There will be a ton of it, as several nine-figure contracts will be negotiated in the coming weeks. None will be bigger, of course, than Juan Soto’s. But how big will it be? And for how long? And with whom? 

Accordingly, FOX Sports MLB experts Rowan Kavner and Deesha Thosar weigh in on Soto, as well as a trio of aces and what teams will likely be the most active this winter in our latest roundtable.

1. There was a report that Alex Bregman is seeking a deal close to Manny Machado’s 11-year, $350 million extension. What is the max deal you’d offer Bregman if you were a GM, and what team should be most aggressive in signing him?

Thosar: Well, Bregman vying to get close to Machado’s extension is overshooting just a little bit. I think he lands a deal in the AAV range of $26-28 million, and if he wants a long-term deal that’s going to eclipse the $200 million mark, then a seven-year deal for $200 million should be achievable for the longtime Astros third baseman. That’s as high as I’d go because Bregman would be 37 by the end of that deal, he already has a lot of mileage underneath him since his 2016 MLB debut, and there was one big concern this year with his walk rate, which was slashed in half in a huge departure from his career norm. Though I can’t imagine Bregman in another uniform besides Houston, the Phillies would be significantly upgraded with the third baseman replacing Alec Bohm. The Phillies are desperate to win the World Series with their tight-knit group before some core players depart for free agency, and adding Bregman to the mix would immediately make them one of the favorites to win it all.

Kavner: Bregman might not be the MVP candidate he was five years ago, but he is still a consistently well-above-average hitter who brings elite defense, rarely whiffs or strikes out and is good for around 20-25 homers a year. His hard-hit rate was actually the highest of his career last season, though it has to be at least a little concerning that the 30-year-old’s walk rate suddenly plummeted, that he chased a bit more than usual, and that he outperformed his expected stats in 2024.

There would be a lot of factors determining the max I’d offer, including the team I’m managing and the payroll I’m working with. If I were making decisions, I’d love to possess the financial freedom to add and extend players that A.J. Preller had when he gave Machado that extension prior to Peter Seidler’s passing. The reality is few GMs (including Preller now) can run the bill up so freely. While Bregman should easily exceed the six-year, $151 million extension that Matt Chapman received in San Francisco, I’d be stunned if he got anything close to Machado’s $350 million extension. The max I’d go is around eight years in the $220-225 million range. The Astros are the obvious team to watch, but the Tigers and Mariners should also be aggressive here.

2. Would you rather have Corbin Burnes for seven years, $250M, Blake Snell for five years, $180M or Max Fried for five years, $150M?

Kavner: If they were all getting paid the same I’d go Burnes — there’s a reason he will get the biggest contract of the trio — but at these numbers, I’d take Snell. Burnes is coming off another terrific season, but his descending strikeout rate would frighten me some when I’m offering upwards of $250 million. What I’d choose, though, would depend a bit on my team/roster construction. If I were a team on the fringes of the playoff picture just trying to contend, I’d probably go Fried for his consistency. But his inability to miss bats could cause problems in October (he has a career 3.07 regular season ERA; 5.10 in the postseason), and I’d need more information about the forearm issue that limited him this year. If I’m already a playoff contender looking for a final piece that can help me win a World Series, I’m taking Snell, the two-time Cy Young Award winner who just posted the highest strikeout rate (34.7%) and lowest hard-hit rate (28.7%) of his career. If he’s healthy and looking right in October, there aren’t many people on Earth who can rival his stuff.

Thosar: Max Fried. He shouldn’t hesitate to sign that proposed deal, particularly since he was earning half that amount this year in his All-Star season. Alongside Snell, Fried is the only left-handed ace in this year’s starting pitching class. But executives shouldn’t let the glamour of Snell’s two Cy Young awards get in the way of their decision-making. Fried is a year younger than Snell and more consistent than him, too. Fried, a World Series champion, is the only pitcher in the past five seasons to log over 600 innings and an ERA+ over 150 in the regular season. In the end, I think some of his forearm issues (and his attachment to a qualifying offer, thus resulting in costing whoever signs him a draft pick) will put some ice on his market. He seems likelier to sign a deal with an AAV in the range of $26-28 million.

3. A few weeks back, both of you expected Juan Soto to ultimately re-sign with the Yankees this offseason. How confident are you in that prediction now and what is your best guess for the terms of his deal?

Thosar: I still think the Yankees will ultimately sign Soto, but it’s going to be a tight race between both New York teams. Even though Hal Steinbrenner’s comments at the owners’ meetings in Manhattan on Wednesday were pretty underwhelming and seemed to lack extreme confidence that Soto would end up back in the Bronx, the Yankees owner also indicated that his sole priority this offseason is making sure the slugger returns, and I think he just might do whatever it takes to make sure that it happens. I think Cohen is going to drive the price up, so something like $707 million over 15 years might get the deal done for Soto and the Yankees. But they just can’t let Soto slip away, particularly after he catapulted them to the World Series, and I continue to think they won’t make that mistake.

Kavner: Less! If I were a Yankees fan, I would feel a little queasy after hearing Hal Steinbrenner say “no idea” and “we’ll be in the mix” when asked about his confidence in retaining Soto following their meeting with the soon-to-be-very-rich free agent. I do still expect one of the two New York teams is the ultimate destination, but it feels at least a little more likely now that Steve Cohen’s Mets or another AL East club outbids the Yankees. I think Soto surpasses the $600 million mark but doesn’t get to $700M. Let’s say 14 years, $644 million.

4. Would the Yankees be better off landing Soto on a megadeal, or adding a frontline starter plus two other All-Star bats?

Kavner: Soto. He’s in a different stratosphere from anyone else on the market, and what he provides to the Yankees lineup can’t be overstated. Just look at 2023, when they didn’t have Soto and were an 82-win team with a bottom-10 offense. In 2024 with Soto, they reached the World Series as a 94-win team with a top-three offense. Sure, there were other factors involved, but none bigger than Soto, who gave the Yankees the best 1-2 punch in the sport. He completely transformed the group, and there’s no way to replicate that kind of production.

Thosar: I don’t see why the Yankees, the most lucrative franchise in MLB, should be limited after signing Soto to staying put and putting a cap on their spending. Based on Steinbrenner expressing this week that Soto had questions about the Yankees’ player development system and long-term commitment to winning, the team knows it has work to do this winter to make sure their holes are filled with elite talent. Aaron Judge, before signing his long-term contract two years ago, also wanted confirmation from Steinbrenner that the club’s annual initiative is to win the World Series. So, it’s ultimately in their best interests to land Soto, and then add at least another mid-level starter and an All-Star bat to, at the very least, replace Anthony Rizzo at first.

5. Which playoff team from each league do you project will make the biggest upgrades to their current rosters this offseason? Which non-playoff teams will do the same?

Thosar: The Orioles are on the verge of losing their ace (Corbin Burnes) and home-run leader (Anthony Santander) if they don’t spend the big bucks and keep their top players in Baltimore, so I’m expecting them to make big upgrades not only to fill those holes, but also because this is the first full offseason they can flex their financial might under the new ownership group led by billionaire David Rubenstein. The Mets also have a lot of work to do this winter just to build a starting rotation, and they’re, of course, at the center of conversation with Soto. I’m expecting the Mets, in classic Steve Cohen style, to make at least one big splash this offseason, if not multiple. 

As for non-playoff teams, the Giants have expressed that they want to spend big for multiple offseasons now, only for major deals to fall through or go haywire. Perhaps this is the year, under new president of baseball operations Buster Posey, they are really, truly aggressive and make big upgrades that pay immediate dividends. In the AL, I think this is the winter the Red Sox return to dominance in some way, shape or form. Whether that means landing Soto or a top starting pitcher, Boston has to go for it with a strong offseason after missing the postseason three years straight.

Kavner: The Mets — for obvious reasons, with Cohen’s checkbook backing a team on the rise — and the Tigers, who currently project to have an $80 million payroll. A couple of years ago, this was a team that operated $50 million higher. Even if Detroit doesn’t go crazy this winter, there should be some leeway to spend here, and the Tigers need to add more pop in the infield and starting pitching if they want to build on last year’s surprise run. Could they get involved in the Alex Bregman sweepstakes? At the least, I could see a situation similar to what the Royals did last winter where they give themselves a more viable path toward sustained success.

For the non-playoff teams, I’ll go with two AL East clubs who have already reportedly had meetings with Soto: the Blue Jays and the Red Sox. There’s little point in taking that meeting if you’re not at least considering spending big for difference-making talent. After failing to reel in Shohei Ohtani last winter and then going through the abomination of the 2024 season, the Blue Jays might be tempted to make some considerable overhauls. And for the Red Sox, another false “full-throttle” offseason can’t happen. It’s time to do what it takes to escape the throes of mediocrity. If we want to add a couple of non-playoff NL teams, I’m looking at the Giants and the Nationals.

Rowan Kavner is an MLB writer for FOX Sports. He previously covered the L.A. Dodgers, LA Clippers and Dallas Cowboys. An LSU grad, Rowan was born in California, grew up in Texas, then moved back to the West Coast in 2014. Follow him on Twitter at @RowanKavner.

Deesha Thosar is an MLB reporter for FOX Sports. She previously covered the Mets as a beat reporter for the New York Daily News. The daughter of Indian immigrants, Deesha grew up on Long Island and now lives in Queens. Follow her on Twitter at @DeeshaThosar.

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