Once it became clear that a third last place finish in four years was imminent, the club moved on from chief baseball officer Chaim Bloom and handed the keys to Craig Breslow. Since then the newly-minted baseball boss has mostly worked behind the scenes, enmeshing himself in the organizations and formulating a plan for how to build the Red Sox back into a contender.

That changes this week, and in the coming days we should see Breslow finally begin executing his vision.

Over the next four days the baseball world will gather in Nashville for the annual Winter Meetings, which have historically served as the offseason’s biggest hotbed of activity. Deals will get done, trades will be made, and by next week baseball’s new landscape should come into focus.

The Red Sox are expected to be active, but beyond addressing their own needs there will be other events with industry-wide implications that will affect the club as well, chief among them the MLB Draft Lottery and the Rule 5 Draft.

So what should fans expect in the coming days? Here’s everything you need to know about this year’s Winter Meetings.

Last offseason the free agent market was effectively frozen for the first month after the World Series, but once the Winter Meetings began in San Diego the dam broke and massive deals began breaking left and right.

Justin Verlander. Aaron Judge. Trea Turner. Xander Bogaerts. All came off the board in quick succession, and things only picked up from there.

The biggest fish in the pond this year is Shohei Ohtani, who is expected to land the largest contract in MLB history. The two-way superstar just won his second unanimous MVP award, and even though he won’t pitch in 2024 after undergoing elbow surgery, he’ll still be highly coveted.

Ohtani should be the first and largest domino to fall, and once he resets the market we’ll likely see the other big names start coming off the board.

For the Red Sox, starting pitching is the priority, and there are plenty of arms to be had. Yoshinobu Yamamoto, Jordan Montgomery and Blake Snell represent three of the top starters available and Boston is expected to be heavily involved with all of them.

Boston is also looking for a right-handed bat, an upgrade at second base and possibly another outfielder. The club also needs to make a decision on whether or not to re-sign Justin Turner or go in a different direction at designated hitter.

Where Ohtani looms as the biggest name on the free agent market, Juan Soto once again ranks as the big prize on the trade market.

One and a half seasons after landing the three-time All-Star at the trade deadline for a massive haul of prospects, the San Diego Padres are expected to move Soto and his projected $33 million salary in a bid to cut payroll. Because Soto is now only one year away from free agency he won’t command the incredible price San Diego originally paid, but the Padres can still reasonably expect at least two top 100 prospects in return.

In addition to Soto, several other standout pitchers are also believed to be on the trade block, including Chicago’s Dylan Cease, Milwaukee’s Corbin Burnes, Tampa Bay’s Tyler Glasnow and Cleveland’s Shane Bieber.

 

With a rejuvenated farm system and a surplus of young middle infield talent, the Red Sox are well positioned to swing some deals to bolster their big league roster, something they haven’t done much of over the past four or five years. The club could also explore a trade of starting right fielder Alex Verdugo, who is also one year away from free agency and faces an uncertain future with the club.

One of the first things on the agenda this week in Nashville will be the Hall of Fame’s Contemporary Era Committee election, during which eight longtime managers, executives and umpires will be considered for enshrinement in Cooperstown.

Though none of the candidates had direct ties to the Red Sox, all four managers were notable opponents at one point or another.

Davey Johnson and Jim Leyland managed against the Red Sox in memorable playoff series, with Johnson leading the New York Mets in the 1986 World Series and Leyland the Detroit Tigers in the 2013 American League Championship Series. Lou Piniella played for the New York Yankees during a high point in the Red Sox-Yankees rivalry in the late-1970s before managing against Boston in the AL East with the Yankees (1986-88) and Tampa Bay Rays (2003-05), and Cito Gaston managed the Toronto Blue Jays over two stints between 1989-97 and 2008-10.

The other candidates include umpires Joe West and Ed Montague, executive Hank Peters and National League president Bill White. The election will take place Sunday and the results will be announced on MLB Network at 7:30 p.m.

Castiglione up for Frick Award

Longtime Red Sox radio broadcaster Joe Castiglione is among 10 candidates for this year’s Ford C. Frick Award, which is presented annually by the Hall of Fame to a broadcaster for “major contributions to baseball.”

Castiglione recently completed his 41st season as the Red Sox lead radio voice, and he’s spent 44 years calling big league games overall. He began his career in Cleveland and Milwaukee before debuting in Boston in 1983, and since then he has called all four of the Red Sox modern championships, famously exclaiming “Can you believe it?” after the final out of the 2004 World Series.

Castiglione was also a finalist last winter, when the award went to longtime Chicago Cubs radio broadcaster Pat Hughes.

This year’s other finalists are Joe Buck, Gary Cohen, Jacques Doucet, Tom Hamilton, Ernie Johnson Sr., Ken Korach, Mike Krukow, Duane Kuiper and Dan Shulman. The winner will be announced Tuesday and honored as part of next July’s Hall of Fame Weekend in Cooperstown.

Not long ago Boston’s draft position would already be set in stone. Since the Red Sox finished with the 12th worst record in baseball, they’d be locked into the No. 12 overall pick.

But now thanks to the implementation of the new MLB Draft Lottery, the Red Sox have an outside chance of picking No. 1 overall.

The Red Sox go into the week with a 1.2% chance of winning the lottery and receiving the No. 1 overall pick, and the club has similar odds of moving into the No. 2-6 positions as well. If they don’t win the lottery, the Red Sox will most likely pick somewhere in the No. 11-13 range.

Boston could move up a spot if the New York Mets don’t win the lottery, since the Mets exceeded the second luxury tax threshold and would have their first-round pick moved 10 spots back in such an instance. They could also move back if other teams behind them win the lottery and jump into the top six.

The Oakland Athletics, Kansas City Royals and Colorado Rockies all have the best lottery odds at 18.3% each, and the Washington Nationals are ineligible for the lottery despite finishing with MLB’s fifth worst record since they are a revenue-sharing payor who won the lottery last year. The Draft Lottery is scheduled for Tuesday at 5:30 p.m.

Last year the Red Sox had three pitchers selected in the Rule 5 Draft, including right-hander Thad Ward with the No. 1 overall pick. This year the club has once again left several arms exposed who could be coveted by others.

Baseball America recently identified Red Sox left-handers Shane Drohan and Brendan Cellucci, and right-hander Ryan Fernandez as prospects to watch ahead of the Rule 5 Draft. Drohan in particular is expected to draw wide interest after he was left unprotected at the 40-man roster deadline.

Boston’s No. 18 prospect, according to MLB Pipeline, Drohan got off to a blistering start and was promoted from Double-A to Triple-A after posting a 1.32 ERA with 36 strikeouts in his first six starts with the Portland Sea Dogs. His production fell off dramatically upon his arrival in Worcester, however, and his command, velocity and underlying metrics all regressed as well. Still, that incredible start could prove tantalizing and Drohan’s changeup is regarded as a legitimate out pitch.

As for Cellucci and Fernandez, they’re both relievers who offer intriguing qualities to clubs looking to bolster their bullpen. Cellucci is a lefty whose slider and cutter both draw whiffs at a high rate despite fairly low velocity, and Fernandez is a flamethrower who’s 97 mph fastball ranks among the best of any prospect available in the Rule 5 Draft.

Even if the Red Sox do lose some prospects in the Rule 5 Draft, there is a chance they could still get them back. Though Ward spent all season with the Nationals after his selection last winter, fellow pitchers AJ Politi and Noah Song were eventually returned to Boston after failing to stick with the Orioles and Phillies, respectively.

The Red Sox last selected a player from another organization in the Rule 5 Draft in 2020 when they took Garrett Whitlock from the New York Yankees. That selection is regarded as one of the most impactful Rule 5 additions by any franchise in recent memory.