Key Points
Bullet point summary by AI
- The MLB rumor mill hints at a pivotal offseason for one team facing a tight timeline and budget constraints.
- One player’s slow start hasn’t dampened expectations for a record-breaking contract that could redefine the free agency landscape.
- Upcoming negotiations between MLB and the players’ union could determine the fate of the 2027 season if a salary cap dispute escalates.
Outside of the Patrick Bailey trade that came out of nowhere, the MLB rumor mill is pretty quiet right now, which is to be expected given where we are in the calendar. While there isn't much going on regarding the trade deadline, some murmurs around the coming offseason have begun, specifically revolving around the Chicago Cubs, Jazz Chisholm Jr. and even MLB lockout talk.
With that in mind, let's dive into the latest MLB rumors.
Cubs face dilemma with Ian Happ and Seiya Suzuki approaching free agency

The Chicago Cubs have withstood their pitching injuries to lead MLB's best division to this point, thanks largely to two impending free agents in Ian Happ and Seiya Suzuki. Cubs fans aren't thinking much about those guys hitting the open market just yet, and understandably so. But it is something worth thinking about given how good they are and how this organization tends to operate.
"The Cubs have one of the best records in baseball, but they might have to replace three-fifths of their rotation and both starting corner outfield spots. They also might need to shore up the bullpen. That's a long list of things to do for a contending team going into a winter with a condensed timeline and unpredictable market -- especially for a club that historically hasn't given its executives unlimited payrolls," ESPN's Kiley McDaniel wrote this week.
As McDaniel noted, the Cubs have a lot of work to do this winter, even beyond their outfield, and that's not a great thing when considering that ownership has historically been unwilling to spend much. The ideal world would be Chicago finding a way to keep both Happ and Suzuki, but how likely is that just one offseason after the team already paid guys like Alex Bregman, Pete Crow-Armstrong and Nico Hoerner? And how likely is that when the Cubs have internal replacements like Matt Shaw and Kevin Alcantara in the mix?
This could have trade deadline implications, too. The Cubs probably won't trade one of those two vets given where they are in the standings, but would they hesitate more when teams call about Alcantara and Shaw? It'll be interesting to see how Jed Hoyer navigates this.
Slow start has not derailed Jazz Chisholm Jr.'s expected free agency market

Jazz Chisholm Jr.'s season is off to a nightmarish start, which is not good for a New York Yankees team in World Series contention — and for an infielder who is looking to earn a massive contract in free agency. He doesn't even have the cold-weather excuse anymore. He's slashing .201/.281/.322 with four home runs and 14 RBI this season, and his 73 wRC+ is good for 153rd out of 177 qualified position players. As bad as he's been, though, McDaniel does not believe Chisholm's market has been impacted much at all.
"There might not be another slam dunk nine-figure player, with Freddy Peralta and Jazz Chisholm Jr. having the strongest cases at the moment among the other pending free agents," McDaniel wrote.
McDaniel believes that outside of Tarik Skubal, Chisholm Jr. might have the best chance of anyone in the upcoming free agency class to secure a nine-figure deal. As weird as that might seem for a player who is struggling to hit above the Mendoza Line, it does make sense.
When right, Chisholm is a bona fide star. He can hit 30+ home runs, steal 30+ bases and play elite defense up the middle. He might be the most well-rounded second baseman in the game at his best, and he's just only 28 years old. Yes, he's struggling right now, but his track record suggests he'll turn it on sooner rather than later, and once he does, with the position he plays and his age in mind, it'll be surprising if Chisholm Jr. doesn't earn the biggest contract of any position player this offseason.
Everything you need to know about lockout negotiations

The MLB and MLBPA met on Tuesday for the first time ahead of what's widely expected to be a lockout when the Collective Bargaining Agreement expires at 11:59 p.m. ET on Dec. 1. Now, specific proposals have not begun yet, but The Athletic's Evan Drellich reported that the meeting was for the owners and the MLBPA to give opening presentations.
"The league is expected to propose a salary cap and salary floor, changes that owners will frame as a means of improving competitive balance. Players in the past have vehemently fought against a cap-and-floor system for a variety of reasons, many of them economic. If both sides now dig in, the ensuing fight could threaten the 2027 season," Drellich wrote.
The center of these conversations will certainly revolve around a salary cap, which is something owners are insisting on implementing and something that players have always been vehemently against. If they cannot come to a resolution on this, a lockout is a near certainty, and that could put the 2027 season at risk. Here are other things to know.
- A baseball CBA typically covers five seasons of play.
- Movement on proposals might not be significant until the winter.
- If a deal can't be reached by March, schedule adjustments will likely have to be made.
- A lockout puts an end to all transactions, including signings and trades.
It'll be interesting to see what happens. The last thing this sport needs right now, when it's seemingly as popular and growing as rapidly as ever, is a lockout. Hopefully, the two sides can work something out to avoid any work stoppages.
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