MLB Offseason Mailbag: Peralta’s future, Skubal buzz, Red Sox moves and more

The MLB offseason is already a couple weeks old, and I just got back from the GM Meetings in Las Vegas. So what better time for a Q&A? I asked folks on X to send me their best questions as it pertains to the Hot Stove. Could Milwaukee Brewers ace Freddy Peralta be traded? What could the Boston Red Sox do to upgrade their pitching staff? Is Tarik Skubal going to get moved? Answers to all that and much more are below.

Brewers: Will Milwaukee trade Freddy Peralta?

I don’t like doing percentages. But I do think the chances of a Peralta trade went up after Brandon Woodruff accepted the qualifying offer on Tuesday afternoon.

At the GM Meetings, president Matt Arnold said that he “anticipates [Peralta] being part of our team moving forward.” He added that almost every team is interested in Peralta, and that he’ll listen because “we’re the smallest market in the league.”

But executives around the league wonder if the Brewers will be more open to moving Peralta now that Woodruff is signed for 2026. After all, Woodruff is earning $22.025 million and Peralta is earning $8 million; $30 million for two pitchers, to a small-market franchise, is a lot. It’s possible, of course, that Woodruff could sign a multi-year contract to lessen the money due next season. But even then, team owner Mark Attanasio told The Athletic that he doesn’t see Woodruff returning as a “prelude” to trading Peralta, saying: “Independent decisions Matt and his group will make. We’re certainly excited about our rotation now.”

The Brewers prefer to keep Peralta and value him immensely, both on and off the field having watched him practically grow up with the organization. But Arnold and Attanasio have not ruled out a trade. And I could see the interest being so strong that it leads to a Peralta trade being a real possibility.

White Sox: Is Chicago's interest in Ryan O'Hearn for real?

They’re interested. To what extent, I’m not sure. But O’Hearn, 32, is coming off a season in which he hit .281/.366/.437 with 17 home runs and 63 RBI. He hits left-handed pitching well for a lefty and is widely praised for being a high-character presence in the clubhouse. He’d be a really good fit in a young White Sox roster. That said, he’s drawing plenty of other interest.

Blue Jays: Is a Bo Bichette–Kyle Tucker combo a pipe dream?

My guess is that it would be one or the other because of the overall contracts that each will command. But I’ve consistently heard from people around baseball that players love playing in Toronto. It’s a desirable place to be, and we’ve seen that reflected in Shane Bieber’s decision to stay with the Blue Jays for $16 million next season. Coming as close as they did to winning a World Series … other players are going to want to be part of that.

Mets: Can New York pull off a Tarik Skubal trade?

I don’t believe any team trades for Skubal. The Tigers really value him and he loves being in Detroit. With the reported gap in extension talks, I can’t see a long-term contract being reached this offseason. So my feeling is that the Tigers keep Skubal, he plays out the season in Detroit and then he tests free agency next offseason.

Eggs scrambled or over easy?

Neither. Eggs are trash.

Padres: Assessing San Diego's chances of a free agency splash

You can never rule out anything with the Padres, especially with AJ Preller running the show. But a major signing would surprise me.

The Padres’ biggest need is starting pitching. Yu Darvish is out for the 2026 season after undergoing surgery to repair his ulnar collateral ligament. The current rotation has Nick Pivetta, Joe Musgrove, Randy Vasquez and a lot of uncertainty behind them. San Diego also needs a first baseman, too, and there are question marks in the bullpen with Robert Suarez a free agent and Jason Adam returning from a ruptured quad tendon (although word is his recovery is going very well).

That's a lot of holes to fill, and the team's uncertain financial future clouds things even further.

Yankees: Does New York extend Jazz Chisholm this offseason?

The Yankees typically do not offer contract extensions, as they prefer to allow players to establish their values on the open market. There have been exceptions, of course, most notably when they tried extending Aaron Judge in 2022. And Chisholm could be another one, as general manager Brian Cashman did not dismiss the idea outright when asked last week.

“I guess that remains to be seen,” Cashman told reporters at the GM Meetings.

He added: “Not sure how that would play out. But we have not had any conversations outside of he’s looking forward to playing next year, he loves playing here, and if we’re open to, if you want to have a legitimate conversation about value, (he’s) open to a longer-term conversation as well.”

Chisholm, 27, is coming off a terrific season in the Bronx, hitting .242/.332/.481 with an .813 OPS, 31 home runs and 80 RBI. He also made his second All-Star appearance. His value entering the final season of his contract is enormous, and it would take quite an offer to entice him to forego free agency. My best guess is that he plays out the year on his current deal and enters the market after the 2026 season.

Red Sox: How many pitchers will Boston add?

At the GM Meetings, Breslow told me that the team will pursue a middle-of-the-order bat and a meaningful addition to the rotation. He wants someone who can slot in alongside or behind Garrett Crochet and start playoff games. He also told MLB.com that he feels “pretty good about overall starting pitching and Nos. 3-ish through 10-ish.”

My read: multiple starters would appear unlikely.

For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop during the MLB season.