We’re about a quarter of the way through the 2026 Major League Baseball season, and while storylines for the rest of the year are coming together, let’s skip ahead to the offseason.
There are many elements to consider already: Tarik Skubal‘s elbow surgery, labor negotiations getting underway, a potentially expedited pre-lockout free agency, big market clubs such as the New York Mets and Philadelphia Phillies swooning early, and a muddy free agent class beyond Skubal add to the intrigue around the upcoming winter.
Here are the topics that come up most often with MLB executives, scouts and agents surrounding 2026-27 free agency.
1. What will Skubal’s market look like following his third elbow procedure?
Skubal had Tommy John surgery in college in 2016, had flexor tendon surgery in August 2022 and just underwent surgery to remove loose bodies in his left elbow earlier this month. The first two procedures had already come up when I asked executives, scouts and agents to project Skubal’s potential payday over the past six months, but now there’s another procedure on the 29-year-old’s résumé.
The morning the latest surgery was announced, I was texting those same people as part of an industry straw poll on what Skubal’s contract would be. Seven of them got back to me before the news broke. The average of those projections was 7.7 years for $357 million, or just over $46 million per year. Among pitchers, that would beat Max Scherzer‘s average annual value record of $43.3 million and Yoshinobu Yamamoto‘s guaranteed money mark of $325 million (over 12 years). I’m confident the results would have looked similar if I had gotten the 20 or so responses I normally collect for straw polls.
The assumption is that Skubal will return this season looking close to the same pitcher he has been recently, and his agent has stated it could be a relatively short absence, but he could land a lower price in free agency due to the renewed durability questions after this surgery. It’s impossible to predict exactly how he’ll appear on the mound after returning, what his market will look like at that point and whether the MLB labor situation will affect his negotiations. Sources agreed, though, that the chances that Skubal will go back to the Detroit Tigers on a shorter-term deal with opt-outs is much higher than it was before this injury.
2. How will the potential work stoppage affect free agency?
Though we don’t know for sure, we can use the last collective bargaining agreement negotiations and subsequent lockout as a guide. Teams looking to devote big money to making upgrades generally want to do so before the current CBA expires Dec. 1, both to avoid waiting for key additions and as a pre-negotiation signal of healthy spending on players. (The Texas Rangers splurging on Corey Seager and Marcus Semien for a combined $500 million hours before the Dec. 1, 2021, deadline was notable from that pre-lockout period.)
The assumption is that a lockout will happen again. That naturally leads to two questions: Which teams are eager enough to spend to sign big-ticket players before Dec. 1? And which players are important enough to get the offers they’d want to sign before the CBA expires? Prior to his injury, Skubal was the top free agent, but now his market might be muddier, which could lead to his camp opting to wait a bit. 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.
3. Who is the top position player?
There are a number of solid candidates to consider, but no clear top dog.
In the infield, Chisholm is the leading choice, with J.P. Crawford, Brandon Lowe, Isaac Paredes, Luis Arraez and Yandy Diaz among the other options. I don’t think Bo Bichette is on track to opt out of his deal, but he’ll be on that list of players if he decides to forgo the two remaining years of his contract at $42 million per season.
In the outfield, a number of roughly similar players will sort themselves out during the season: Daulton Varsho, Seiya Suzuki, Randy Arozarena, Ian Happ, Taylor Ward, Trent Grisham and, likely looking for a shorter-term deal, George Springer.
For a team such as the Boston Red Sox that would like to add power next winter, there are solid options but not necessarily the exciting group of names fans hope to see. Given the lack of high-end position players, there’s a belief that the trade market will be more active than usual this offseason, but probably after the expected lockout rather than before.
The depth of the 2026-27 free agent market is starting pitching. The leading names behind Skubal and Peralta are: Trevor Rogers, Michael King (opt-out), Kevin Gausman, Tatsuya Imai (opt-out), Kris Bubic, Jack Flaherty, Joe Ryan (mutual option), Zac Gallen, Shota Imanaga, Casey Mize, Nick Pivetta, Brady Singer, Shane Bieber, Brandon Woodruff, Nick Martinez (mutual option), Matthew Boyd (mutual option) and Clay Holmes (opt-out).
4. What effect would a lockout have on the posting market?
With a 45-day window needed to go through the posting process, the potential lockout date constricts the options of Korean and Japanese clubs. They could either jump in at the first possible posting date or basically miss the whole offseason because of the potential for a rush at the end, which could come after new seasons start in Korea and Japan.
MLB team executives think a lockout would speed up the process for fringe players who don’t know whether they have a market with MLB teams, so they’d go for that early window to get the necessary feedback. Players who know they’re in for a big payday should be fine waiting until after the CBA is resolved, or even until the next offseason. Because of the potential complications and tightened windows for lower-end free agents who often end up in NPB anyway, Japan might be a more attractive option next season for a number of players.
In addition, the crop of potential posting candidates isn’t as strong as it has been in past years. At this time last year, for example, we knew Munetaka Murakami would be a big name in the winter. There are still a handful of NPB pitchers worth monitoring, but they’ve largely been struggling or hurt of late.
5. What will the Mets and Chicago Cubs do?
The Mets have the worst record in baseball — and the sport’s second-highest payroll. The roster overhaul from the winter isn’t working right now, but they have a little over $71 million likely to come off the books, with Bichette’s potential opt-out of a $42 million salary a big variable not included in that figure.
The $71 million includes Peralta, Holmes, David Peterson, Brooks Raley and Luis Robert Jr., though prospects Jonah Tong, Jack Wenninger and A.J. Ewing could fill some of those spots — potentially giving the Mets an opportunity to re-sign one or two from the veteran group, then use the additional money for an upgrade or depth at another position.
Chicago has more than $100 million in potentially expiring contracts (depending on option decisions), which is just under half of its payroll. 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.
