MLB Rumors: Sasaki sets meetings, new Red Sox target, Jackson Holliday uncertainty

The Winter Meetings are in full swing and MLB rumors are flying. Today, Roki Sasaki, the Red Sox and Jackson Holliday are in the center of everything.
World Baseball Classic Semifinals: Mexico v Japan
World Baseball Classic Semifinals: Mexico v Japan / Eric Espada/GettyImages
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We are now in the heart of the MLB winter meetings, and we've seen a ton of movement thus far. Today, we have some more news and rumors of the latest going around MLB, including Roki Sasaki news, the Boston Red Sox looking to land ace Dylan Cease, who was surprisingly made available, and a tidbit on Jackson Holliday entering his second full season with the Orioles. Let's dive in.

3. Roki Sasaki setting meetings

One of the biggest stories to watch from here on out will be the Roki Sasaki Sweepstakes. With seemingly all teams interested, rumors will persist until the day he signs, likely just after Jan. 15, when the new international amateur free-agent period begins. Meanwhile, Sasaki is set to start meeting with teams, perhaps as soon as next week, return to Japan for the holidays, and then come back at some point after that to make his decision.

Sasaki has ace potential at just 23 years old and will cost the bare minimum to a contract on a minor league deal, where he will, without a doubt, break camp with whichever roster he is on and be utilized as a frontline starter the first year he is in MLB. Many factors will influence his decision, including what his Japanese counterparts have done, and he has strongly emphasized player development and a team's willingness to compete.

For more news and rumors, check out MLB Insider Robert Murray’s work on The Baseball Insiders podcast, subscribe to The Moonshot, our weekly MLB newsletter, and join the discord to get the inside scoop during the MLB offseason.

2. Red Sox pursuing Dylan Cease

Interestingly enough, the San Diego Padres may be looking to shop Dylan Cease, which may be a monumental mistake, given that they are an early favorite to land Sasaki, who values a team that is looking to be competitive. If that's the case, now is not the time to trade away an ace who the Boston Red Sox are now in hot pursuit of, according to MLB insider Jon Morosi.

After playing the waiting game with Juan Soto, the Red Sox missed on Blake Snell, Tyler O'Neill, and how now missed on Max Fried and Nathan Eovaldi. Of the big free-agent pitchers, Corbin Burnes remains, who Boston will likely have to face stiff competition to land. The best route for the Red Sox, who need to make a serious splash this winter, to acquire a top-tier starting pitcher is trade. Garrett Crochet and Cease should be a high priority for the team, so it's no surprise to see them involved here. More to come.

1. Jackson Holliday not penciled to Opening Day plans

When Brandon Hyde was asked if former top prospect Jackson Holliday was a lock for the starting lineup, Hyde responded with, "I'm not writing it in. I'm definitely keeping the options open. ... He's going to get every opportunity to get as many at-bats as possible." Holliday, who received 190 at-bats last season, slashed just .189/.255/.311 in his first major league season. Still just 21 years old, Holliday's ceiling is sky-high, and he must develop at the highest level to reach his full potential.

He has adjusted at every level, slashing .304/.443/.486 in the minors, including batting .271 for Triple-A Norfolk in 2024, but the jump to the majors is a big one, and it's not surprising that somebody his age struggled. Most players his age are getting drafted out of college and heading to Single-A, where Jackson is already set to make a name for himself on the grandest stage. It's not far-fetched to believe he'll have a much better season in year two.

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