When will the 'Big Four' sign? Insiders answer lingering Hot Stove questions

By next Thursday, all 30 teams’ pitchers and catchers will have reported to Spring Training, and we are less than six weeks away from the season-opening Seoul Series between the Dodgers and Padres in South Korea.

But while the clock is very much ticking on the offseason, a number of notable free agents remain on the open market. To find out how that situation may play out over the coming week -- and perhaps beyond -- we asked insiders Mark Feinsand and Jon Paul Morosi to address some lingering Hot Stove questions.

1) Do you think any of the “Big Four” free agents remaining (Cody Bellinger, Matt Chapman, Jordan Montgomery and Blake Snell) will sign by next Thursday? Which one seems most likely to do so?

Feinsand: As we have discussed for weeks, all four players are represented by agent Scott Boras, who has never been afraid to wait for the right deal. The one that seems most likely by next week is Montgomery, who seems destined for a reunion with the Rangers if the two sides can agree on a number.

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Morosi: I believe Montgomery will sign by Thursday. There is greater incentive for pitchers to sign than position players, because they generally need more time in camp to prepare for the regular season. The Rangers are the favorites to sign him, but I wonder if the Red Sox could make a late push by clearing salary with a Kenley Jansen trade.

2) Is there a chance that any of those players sees his free agency drag past Opening Day?

Feinsand: As I mentioned before, Boras has never been one to panic as the season approaches. It would be unusual for players of this magnitude to remain unsigned when the season opens, but it wouldn’t be unprecedented. In 2019, Dallas Keuchel didn’t sign until June, while Kendrys Morales and Stephen Drew did the same in '14. Those situations were largely brought about as a result of the qualifying offer, which operated under different rules back then. But to think that none of these four players might find themselves without new deals come Opening Day isn’t crazy by any means. A Spring Training injury could also impact a club’s desire/need to sign one of the four free agents.

Morosi: There is certainly a chance, but I do not see those odds as likely, especially for Montgomery and Snell. Clearly, the market has not unfolded the way they expected, but both are young enough that they can have a more successful experience on the open market during the 2024-25 offseason. Of course, the only way that happens is with a strong performance in ‘24; the chances of that improve by signing early enough to have a steady competitive progression into the regular season.

3) Picking from that Big Four, which player-team pairing do you think is most likely to come to fruition, whether it’s before or after the start of Spring Training?

Feinsand: I would have to go with Montgomery and the Rangers, though a reunion between Bellinger and the Cubs feels just as likely. Chicago hasn’t replaced Bellinger’s bat in its lineup this winter, and unless the Cubs pivot to Chapman, the need to bring back Bellinger continues. It feels like the Giants will be in play for Snell, Bellinger and/or Chapman, so I wouldn't be shocked if San Francisco winds up with at least one of them.

Morosi: I don’t see a better fit than a reunion for Bellinger and the North Siders. The Cubs have flexibility at his two positions -- first base and center field -- and Bellinger found a home in Chicago after struggling mightily near the end of his tenure as a Dodger. And though he’s not listed as one of the Big Four, I see Jorge Soler and the Giants as a strong possibility, as Susan Slusser indicated recently in the San Francisco Chronicle.

4) Is there a team that did not originally seem to be a likely destination for one of those players that could sneak in and make a serious play now that their situations remain unresolved at this late date?

Feinsand: There has been some buzz about the Phillies jumping in for either Snell or Montgomery, and while Dave Dombrowski has said that he doesn’t expect any major moves from this point forward, he did leave the door open during a recent radio interview on 94 WIP-FM, saying, “I can’t tell you that somebody doesn’t fall into your lap at some point where you say, 'Gee, that’s an opportunity we can’t turn down.'”

Morosi: I agree with Mark that the Phillies are a prime candidate. They’ve had a quiet offseason, and Dombrowski once signed Prince Fielder to a $214 million contract in late January. The Red Sox could fit this description, too, but only if they’re able to clear payroll by moving Jansen’s contract.

5) The two biggest names outside that quartet are probably Soler and J.D. Martinez. How do their markets overlap, or contrast, now that a number of other big bats have come off the board in recent weeks?

Feinsand: Martinez and Soler are the two best designated hitters left on the market, though Soler can also play a corner-outfield spot, giving him more versatility to potential suitors. The Giants have been connected to Soler in recent days, while the Mets have been reported as a potential landing spot for Martinez. It’s hard to think that their markets don’t overlap, though, as they are the two premier power bats still available in free agency.

Morosi: Their markets are different, in that I believe Soler will sign a two-year contract while Martinez is probably looking at a one-year deal. The Blue Jays and Soler had substantive talks earlier in the offseason, before the Jays ultimately signed Justin Turner to a one-year, $13 million deal.

6) In the wake of Corbin Burnes heading from Milwaukee to Baltimore, do you expect any other major trades prior to Opening Day? Who is one notable player who still could be moved?

Feinsand: The Brewers are still the team to watch on the trade front, especially after they traded Burnes. Devin Williams and Willy Adames are the two notable players in Milwaukee who could still be dealt, with Adames -- who is slated to become a free agent at the end of the season -- the more likely of the two. Williams, who won the 2023 Trevor Hoffman Award as the NL’s top reliever, is under club control through the end of 2025, but with young fireballer Abner Uribe waiting in the wings to take over the closer’s job, the Brewers could trade Williams to address other areas of need on the roster.

Morosi: My bold prediction is that the Marlins will make a significant trade before Opening Day. Peter Bendix has had a quiet first offseason with the team, meaning this camp in Jupiter, Fla., is a crucial evaluation period for him. After seeing his personnel up close, perhaps he’ll be more comfortable moving one of his young starting pitchers for a position player-focused package of young talent.