With the 2026 MLB season roughly one-quarter complete, current narratives are taking shape, but it's worth fast-forwarding to the winter period ahead.

Several factors are already in play: Tarik Skubal's recent elbow operation, emerging labor talks, possible rushed free agency before a lockout, struggles from high-payroll teams like the New York Mets and Philadelphia Phillies, and a unclear free agent pool outside of Skubal all heighten the interest in the coming months.

These are the issues most frequently raised by MLB executives, scouts, and agents when discussing 2026-27 free agency.

1. How will Skubal's market shape up after his third elbow surgery?

Skubal underwent Tommy John surgery during his college days in 2016, flexor tendon repair in August 2022, and most recently had loose bodies removed from his left elbow this month. Executives, scouts, and agents had already noted the prior surgeries when estimating his contract value over the last half-year, but this latest one adds to the 29-year-old's medical history.

On the day his newest procedure was revealed, I surveyed contacts in the industry via text about Skubal's potential deal. Seven responded before the announcement, averaging 7.7 years and $357 million - more than $46 million annually. That would surpass Max Scherzer's $43.3 million AAV record among pitchers and Yoshinobu Yamamoto's $325 million guarantee over 12 years. I expect similar outcomes from a full poll of 20-plus sources.

Expectations hold that Skubal returns this year performing near his recent form, with his representative indicating a brief recovery. Still, free agency value could dip amid fresh concerns over his long-term reliability post-surgery. It's tough to forecast his on-field results upon comeback, market dynamics then, or labor impacts on talks. Insiders concur that odds of a shorter pact with opt-outs back to Detroit Tigers have risen significantly since the injury.

2. In what ways might a work stoppage influence free agency?

Drawing from prior CBA discussions and the ensuing lockout, teams aiming for major investments typically act before the current agreement ends on Dec. 1 - sidestepping delays for key pieces and signaling robust player spending. (Recall the Texas Rangers' $500 million outlay on Corey Seager and Marcus Semien right before the 2021 deadline.)

A repeat lockout seems probable, prompting queries: Which clubs will pursue premium talent pre-Dec. 1? Which free agents command deals worth jumping early? Pre-injury, Skubal led the class, but uncertainty now might prompt his side to hold off. Lacking another obvious $100 million-plus star, Freddy Peralta and Jazz Chisholm Jr. stand out most among remaining free agents.

3. Which position player emerges as the best available?

Several viable options exist, yet none dominates clearly.

Among infielders, Chisholm leads, followed by J.P. Crawford, Brandon Lowe, Luis Arraez, and Yandy Diaz. Bo Bichette might test free agency via opt-out, despite two years left at $42 million yearly.

Outfielders feature comparable talents like Daulton Varsho, Seiya Suzuki, Randy Arozarena, Ian Happ, Taylor Ward, Trent Grisham, and George Springer seeking shorter terms.

For power-needy squads like the Boston Red Sox, choices abound but lack star power fans crave. With thin elite position player ranks, trades could heat up unusually - likely post-lockout.

Starting pitching offers the deepest free agent group. After Skubal and Peralta: Trevor Rogers, Michael King (opt-out), Kevin Gausman, Tatsuya Imai (opt-out), Kris Bubic, Jack Flaherty, 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. How would a lockout impact the international posting system?

The 45-day posting timeline clashes with a potential lockout, limiting choices for Korean and Japanese teams. They might post early or risk missing out amid end-of-offseason chaos, possibly overlapping new domestic seasons.

Executives anticipate acceleration for borderline players needing MLB interest signals, targeting the initial window. Proven high-value talents can afford to wait post-CBA or into 2027. Tightened schedules may steer lesser free agents toward Nippon Professional Baseball.

Moreover, this year's posting prospects pale versus recent vintages - no standout like last year's Munetaka Murakami. A few NPB arms merit watching, though recent form has faltered amid injuries.

5. What's next for the Mets and Cubs?

The Mets own MLB's worst mark alongside the league's No. 2 payroll. Their offseason rebuild falters currently, but over $71 million sheds soon - excluding Bo Bichette's possible $42 million opt-out.

That sum covers Peralta, Holmes, David Peterson, Brooks Raley, and Luis Robert Jr., with prospects Jonah Tong, Jack Wenninger, and A.J. Ewing possibly stepping in. This frees cash to retain select veterans or bolster elsewhere.

The Cubs face over $100 million in expiring deals (options pending), nearly half their payroll. Despite a top record, they risk losing three-fifths of the rotation and corner outfield starters, plus bullpen needs. Contenders rarely juggle such lists amid squeezed timelines and volatile markets - particularly for a franchise not known for blank-check budgets.