CINCINNATI, OHIO – SEPTEMBER 14: Tarik Skubal #29 of the Los Angeles Dodgers gets set to throw a pitch in the first inning during a game against the Cincinnati Reds at Great American Ball Park on September 14, 2026, in Cincinnati, Ohio. (Photo by Brandon Sloter/Getty Images)
LAS VEGAS, NV—The first major event of the 2026-27 Major League Baseball offseason is set to take place later today in Las Vegas, Nevada, with the start of the annual General Manager Meetings.
However, unlike in past years, this year’s meetings will draw more attention as we sit just weeks away from the inevitable lockout between league owners and the MLB Players Association, meaning no trades. Signings and any offseason movement will be off the table until a new Collective Bargaining Agreement is put in place.
Still, we’ve been in this situation before: shortly after the 2021 season, the league went into a similar lockout, which in turn created a short free-agent frenzy just after that offseason GM Meeting.
For the Los Angeles Dodgers and their front office, it’s the start of planning for their 2027 roster, intending to rebound after an embarrassing NLCS loss to the eventual World Series Champion Milwaukee Brewers and hopefully returning to the Fall Classic.
So what major questions follow Los Angeles this time around as the first key date of the long winter? Let’s discuss.
This is a question many fanbases will wonder about their own teams over the final days of November and into the Thanksgiving holiday.
For the Dodgers, they’re currently the boogeyman in the latest labor negotiations, with opposing fanbases and other league owners pointing at Los Angeles as the reason for the league-wide disparity in chances to win.
Because of that, most of the talk during this year’s negotiation period will focus on implementing a salary cap in the sport, which would counter the Dodgers’ careless spending over the last several offseasons under owner Mark Walter.
Even if a cap is placed and many of the Dodgers’ contracts are grandfathered in, it will still cause an issue for the Dodgers’ financial outlook with so much uncertainty about whether it’s business as usual or having to keep an eye on every dollar spent.
That sentiment reportedly remains true, as many insiders suggest the Dodgers will likely fill their needs internally or via trade, as David Vassegh of Dodger Talk noted.
“It feels like the (Tarik) Skubal chip, once that moves, Freddy Peralta and Michael King may move as well. I think those three are the ones that are looking to sign the most before December 1. To me, outside of Skubal, I feel like the Dodgers are looking at trade partners before December 1 with the uncertainty of how a new CBA will look,” David Vassegh said on SportsNet LA.
“Shorter-term deals, ideally maybe a player that only has one year left on his contract, like the Houston Astros’ shortstop Jeremy Peña. There are reports that the Astros are listening to offers for Jeremy Peña, who becomes a free agent after one more year. That would be an ideal type of guy in a trade partner for the Dodgers.”
Still, the main player holding up the Dodgers’ offseason plans is left-hander Tarik Skubal, who is likely to sign before the December 1st lockout to cash in on the current financial system in place, where he’ll seek to top Yoshinobu Yamamoto’s 12-year, $325 million deal.
Let’s stay with Skubal now, shall we?
While Skubal was initially thought to be a true one-year rental for the Dodgers, the two-time American League Cy Young Award winner enjoyed his time in Los Angeles, and a potential reunion could be in place for the right deal.
Still, as Katie Woo of The Athletic pointed out multiple times last week on radio and in her recent newsletters, the Dodgers would only seriously entertain a Skubal reunion if it were on a deal similar to the one Kyle Tucker signed last winter: short-term, high-AAV.
That contract structure is also similar to what fellow MLB insider Buster Olney has heard through the grapevine, stating that a 6-year deal with around $60 million could be a very real possibility for the lefty this winter, which would give Skubal, 30, the highest AAV and contract value for a starting pitcher in MLB history.
If the Dodgers go that route, they’d likely try to deal away a starter earning top dollar in their rotation, such as Blake Snell or Tyler Glasnow, to create payroll flexibility while also monitoring the opt-out clause in Yamamoto’s contract.
Still, even on a 6-year contract worth over $60 million per year, it is a massive financial commitment for Los Angeles, and with the possibility of baseball’s economic landscape changing, they’re likely to hold off.
The Dodgers will enter the winter with one of the league’s best farm systems; however, with multiple players under contract for the foreseeable future, Brandon Gomes and Andrew Furedman will be tasked with injecting youth into the roster without a complete teardown.
A storyline that followed Los Angeles all season, and was apparent in October, was that the team has the oldest posting player roster in the league, and nealry all of those players will be back in 2027.
One name that has been connected in trade rumors in the past is outfielder Teoscar Hernández, who is entering the final year of his contract, along with a team option for 2028.
A move on Hernández would open the door for a full-time role for top prospect Josue De Paula, but the Dodgers remain hesitant to do so given De Paula’s limited defensive skill set.
Even after De Paula, another player, James Tibbs III, is arguably a more finished product, a first baseman/outfielder who had a fantastic season for the Triple-A Oklahoma City Comets but was never given the chance to be called up to the big-league level, as the team did not have to promote him to the 40-man roster until next winter.