Former Red Sox pitcher Curt Schilling might have to sell or give up the famed blood-stained sock he wore on the team's way to the 2004 World Series championship to cover millions of dollars in loans he guaranteed to his failed video game company.
The Red Sox lost another key member of their front office Monday, when vice-president of amateur and international scouting Amiel Sawdaye followed former general manager Mike Hazen to Arizona.
Sawdaye will be the Diamondbacks' assistant GM. As stated by Rotoworld, he had been instrumental in building up the Red Sox' young big league talent and farm system.
The Boston Globe reported today that the Red Sox may not fill the GM vacancy created when Hazen left, instead using "other staffers to take on Hazen’s administrative duties". President of baseball operations Dave Dombrowski handles many of the duties traditionally associated with the general manager's position, leaving the actual GM's job in Boston as "essentially an assistant [position] with a lofty title but little power".
The Red Sox have also lost two other front-office members this offseason: Senior baseball analyst Tom Tippett, who had been with the organization for eight years, and director of sports medicine services Dan Dyrek, who had been with the Sox for five years.
Sometime over the next 10 or so days, either the Chicago Cubs or Cleveland Indians will win the 2016 World Series.
Naturally, that will mean one of baseball's two longest-suffering franchises will end their championship drought. Either the Cubs will win their first title since 1908, or the Indians will win for the first time since 1948.
That alone should make for an epic World Series.
But there's another bit of history at stake, too - one of legacies.
In addition to the great discomfort felt by Red Sox ownership -- which fired the manager of one participating team and was seemingly happy to hold the door open for the exit of an executive now running the other - it will also almost certainly result, eventually, in either Terry Francona or Theo Epstein being enshrined into the Hall of Fame.
Epstein would go down as the architect who helped two star-crossed franchises win titles - the Red Sox in 2004, and the Cubs this fall.
The Red Sox went 86 years between championships; the Cubs would be ending a run of futility that stretched across 108 seasons.
That would provide Epstein with an unmatched resume when it comes to degree of difficulty. It's one thing to win it all; it's another altogether to do so with the Sox and Cubs, two clubs, until Epstein's arrival, linked in ignominy.
Epstein could become only the fourth GM in modern history win a World Series in both leagues. Frank Cashen (Orioles and Mets); John Schuerholz (Royals and Braves) and Pat Gillick (Blue Jays and Phillies).
He would also join a short list of executives who have won three rings, a list that includes contemporaries Brian Cashman and Brian Sabean.
Of course, Epstein can't claim to have constructed the entire Cubs roster, no more than he could have done when the Red Sox won in '04.
In Boston, Epstein inherited key players such as Manny Ramirez, Pedro Martinez, Derek Lowe and Jason Varitek. Similarly, Javier Baez and Willson Contreras pre-date Epstein's arrival on the North Side.
But Epstein is responsible for nearly the remainder of the roster, and hiring manager Joe Maddon, the coaching staff and most of the Baseball Operations staff, including GM Jed Hoyer and scouting director Jason McLeod.
Francona's influence on the Indians is just as obvious.
Hired in late 2012 after spending a year in the ESPN broadcast booth, he inherited a team which had suffered through four straight losing seasons. In the five previous years before Francona's hiring, the Indians averaged just over 72 wins per season.
Since his arrival, the Indians have posted four straight winning seasons, with two playoff appearances, while averaging 88 wins per season.
It hasn't seemed to matter to the Indians that they've been without two of their three best starters (Danny Salazar and Carlos Carrasco) this postseason or arguably, their best offensive player for all but 11 games this season (Michael Brantley).
The Indians don't make excuses for injuries, or bemoan their modest payroll. Under Francona, they just win.
This postseason, he's made up for the absences in the rotation by masterfully utilizing reliever Andrew Miller anywhere from the fifth to the ninth inning.
A third World Series would put Francona in similarly rare company. Only 10 managers have won three or more World Series and just six have done so since World War 2 - Walter Alston, Joe Torre, Tony La Russa, Bruce Bochy Sparky Anderson and Casey Stengel.
The individual accomplishments of Epstein and Francona won't take center stage this week and next -- that attention will, rightly, go to their respective beleaguered franchises.
But the subtext shouldn't be overlooked. Once the partying and the parades come to an end, a path to Cooperstown for either the winning manager or winning president of baseball operations can be cleared.