And not unlike the speaking docket, the crowd also contained an established team of developed thinkers. In attendance sat club data scientists, veteran media members and sabermetric luminaries such as Bill James, who is oft-regarded as the face of the advanced-stats movement.
All event proceeds will go to support the Jimmy Fund, an organization doing immense good, said Red Sox utilityman Brock Holt. A 2015 All-Star both on and off the field, Holt serves alongside third baseman Pablo Sandoval as the team's Jimmy Fund co-captain.
"The Jimmy Fund is a real important place for everyone in Boston, especially the Red Sox," Holt said. "A charity that is so close to us. We do a lot of stuff with the Jimmy Fund. I enjoy going over there and hanging out with the kids."
Here's a recap of the weekend's events:
Star power: Schilling took the stage for a lengthy Q&A, during which he conveyed unequivocally his career-long reliance on data.
"I got treated by my teammates [for watching video] like you guys get treated by athletes," Schilling joked.
A 6-foot-5 presence with more than 3,100 career strikeouts, Schilling indicated that he kept a book on more than just the opposing lineups. The 216-game-winner compiled data on each umpire's strike-calling tendencies.
Franchise architects: In a move that surprised no one, Cherington took the stage for the charity event despite his departure from the Red Sox just several days prior.
Though he touched on some of the unmet expectations from his tenure, Cherington nonetheless left Boston with a handful of highlights and reasons for hope. Under him, the Red Sox won the 2013 World Series and developed baseball's top-ranked farm system (per MLB.com).
Still, Cherington was candid about some of the moves -- such as the decision to sign Hanley Ramirez to play left field -- that have so far gone awry.
"We didn't know what he would be defensively in left field, he'd never done it," Cherington said of Ramirez's struggles in the outfield. "So it's impossible to know. We made a bet based on history of what players look like moving from a middle-infield position to another position, and there's data that can help us make an educated guess. He wanted to and seemed committed to doing it. ... It hasn't gone well."
Cherington did caution against grading personnel moves shortly after their consummation, stressing that history cannot be judged until it's played out. One example provided by the former GM: Right-hander John Lackey for righty Joe Kelly and OF/1B Allen Craig, a deal that went down on Trade Deadline Day 2014. Although the move has so far benefited the Cardinals to a much greater degree than the Sox, Boston's Kelly is a hard-throwing hurler with several more seasons of club control. Lackey, meanwhile, is signed only through 2015.
During his time with the mic, Tippett discussed the club's process for prognosticating its own win total. Such analysis, of course, helps guide internal decision-making; teams tend to show greater inclination to add talent and increase payroll when postseason contention is comfortably on the spectrum of possibility.
Late Sunday evening, the Saber Conference came to a close with an auditorium replete with satisfied and more edified attendees. But of course, the greatest winners are those who will benefit from the money raised.
"Our job is to go over there and put a smile on [the kids' faces] and impact their lives," Holt said. "But when we go over there, they do the same for us."