Starr’s 7 Questions: Will Yankees’ first World Series appearance since 2009 motivate Red Sox to go big this offseason?

Seven questions to ponder before the Los Angeles Dodgers and New York Yankees face off in the World Series later this week, the only thing standing between the Red Sox and a pivotal offseason:

1. Will the Yankees’ first trip to the World Series since 2009 motivate the Red Sox this offseason?

Boston has been rebuilding since the end of 2019. In that span, they’ve finished last three times in five years, and only made the postseason in 2021. While Fenway’s attendance plummeted to lows not seen since the previous ownership’s final years, the Red Sox have eschewed extravagant free agent signings, held fast to their top prospects, and fielded embarrassingly low payrolls for a big-market team.

This October needs to be different. Sox brass can talk about not making spending and roster decisions based on rival clubs until the cows come home, but the Red Sox were done by regular-season game No. 162 for the third year in a row, and the Yankees are in the World Series.

At the end-of-year press conference earlier this month, Craig Breslow and team president and CEO Sam Kennedy each said that Red Sox fans had waited long enough. Regarding possible trades, Breslow said everything had to be on the table.

The public, of course, has heard variations of these proclamations before. (It’s almost the one-year anniversary of chairman Tom Werner promising a “full-throttle” offseason.)

Perhaps watching their greatest rivals head back to the Fall Classic will be the straw that breaks the camel’s back.

2. When will the William Felton ‘Bill’ Russell Bridge be complete?

A significant piece of Boston will soon bear the name of its greatest champion. On Monday city officials and members of the Celtics organization gathered to announce that the North Washington Street bridge, which connects Charlestown to Boston’s North End will be renamed the ‘William Felton ‘Bill’ Russell Bridge’ upon completion.

It’s a fitting honor for Russell, the legendary Celtics star, Hall of Famer, the NBA’s first Black coach, and civil rights icon, who passed away in July 2022. The bridge is mere blocks away from TD Garden, and is part of Boston’s Freedom Trail.

However, the bridge isn’t done yet. It’s been an especially arduous process – over six years – given that a temporary bridge had to be constructed to enable vehicles and pedestrians to continue traveling while the rusted old truss bridge was being demolished. According to city officials, the Russell bridge is nearing completion at long last, and will be ‘full open’ by April 2025.

3. How many assistant general managers does one team need?

Breslow spent his first calendar year as Red Sox chief baseball officer without a general manager, but the expected hiring of Taylor Scott to a high-ranking analytics-focused position in the front office could be the ripple effect that finally fills the GM position.

Boston currently has four assistant GMs: Raquel Ferreira, Mike Groopman, Eddie Romero, and Paul Toboni. Scott, whom the Red Sox are poaching from the Tampa Bay Rays, will likely be named a vice president or AGM as well.

Toboni is considered a strong GM candidate, though not necessarily in Boston; the San Francisco Giants recently named their former catcher Buster Posey – who spent his entire professional career with the organization – president of baseball operations, but are also in search of a GM. Toboni, a rapidly rising star in the Red Sox organization, hails from the Bay Area.

4. When did Mookie Betts turn into a postseason supernova?

Some players get their team to the postseason. Others get their team through it. David Ortiz was the rare example of someone who did both.

But for all his greatness during his six Red Sox seasons, Mookie Betts didn’t do much during the three consecutive playoff runs between ‘16-18. Over 21 total postseason games, he hit .227 with a .654 OPS, 20 hits, 17 strikeouts, 10 walks, one home run, and four RBI. He didn’t drive in a single run until his third and final October in Boston, and didn’t homer until the 6th inning of their final World Series game; by then the corks were practically popping out of the champagne in their clubhouse.

Who got the Red Sox into the ‘18 World Series? Jackie Bradley Jr., who took home ALCS MVP honors by driving in nine runs with three extremely clutch hits: a bases-clearing go-ahead RBI double in Game 2, grand slam in Game 3, and go-ahead 2-run homer that made the difference in an 8-6 Red Sox win in Game 4.

Over 48 career postseason games with the Dodgers thus far, Betts has hit .273 with a .819 OPS, 51 hits, 35 strikeouts, 27 walks, seven homers, and 26 RBI. He won his second career World Series ring in his first year in Los Angeles, and gets to vie for another when the Dodgers take on the Yankees later this week.

In no way is this a knock on Betts. He was 23 during that first, brief playoff run in ‘16, and turned 32 earlier this month. He was a star back then, he’s simply shining even brighter now, more accustomed to baseball’s biggest stage.

Yet another reason the trade will go down as one of the biggest blunders in Red Sox history.

5. How many times have the Dodgers and Yankees met in the World Series?

This will be the 12th time the former New York rivals face off in the Fall Classic, but the first time in 43 years. To put that in context, several MLB franchises aren’t even close to 43 years old yet. Five clubs are still without a single championship, including the Seattle Mariners, who were founded in 1977 and are the only Major League team without a single World Series appearance.

The success enjoyed by these two franchises over their respective histories is staggering. The Dodgers, formerly of Brooklyn, won their 25th National League pennant over the weekend and have seven World Series titles to their name. The Yankees have 41 American League pennants and 27 championships (all between 1932-2009); no other team has won more than the St. Louis Cardinals’ 11.

The Yankees have dominated their previous October meetings, 8-3, but it’s an even 2-2 since the Dodgers headed west after the 1957 season.

6. Will Wilyer Abreu be an American League Rookie of the Year finalist?

Wilyer Abreu is already on MLB Pipeline’s 2024 All-Rookie Team last week, and he’s a finalist for AL Outstanding Rookie Award, the Players’ Association announced Monday.

BBWAA’s Rookie of the Year finalists will be announced next month.

7. Did the Yankees try to cheat during the 2004 ALCS?

Netflix’s new ‘03-’04 Red Sox miniseries, ‘The Comeback,’ drops a very interesting little nugget…