The Red Sox, who failed to qualify for the 2019 playoffs after winning the 2018 World Series, had the highest payroll in the league this season at $229.1 million, according to Spotrac. They must fall below $208 million to avoid next year's luxury tax.
"We need to be under the CBT," Henry said, per Kyle Hightower of the Associated Press. "That was something we've known for more than a year now."
Since Boston exceeded the threshold for two consecutive seasons, it faces a potential 50 percent tax for going over $208 million in 2020, per Hightower. The tax would increase to 62 percent at $228 million or a staggering 95 percent at $248 million.
Henry said a fracture began to develop between ownership, which includes chairman Tom Werner, and former president of baseball operations Dave Dombrowski after the World Series triumph over the Los Angeles Dodgers because of differences in planning for the future.
"I was hopeful throughout the year that maybe that perception would change," he said. "It didn't."
Dombrowski was fired in early September amid the club's disappointing title defense.
Ken Rosenthal of The Athletic reported Thursday the Red Sox are "aiming for the biggest names," but the search will be complicated by several factors, highlighted by difficult roster decisions forced by the franchise's salary issues and the impending free agency of superstar outfielder Mookie Betts after 2020.
"One rival executive made a radical suggestion for the Red Sox, saying they should reboot not only by trading right fielder Mookie Betts but also shortstop Xander Bogaerts and left fielder Andrew Benintendi," Rosenthal wrote.
Though it's unclear whether Boston would consider such a massive overhaul, Werner said Friday the club wants to add prospects, per Hightower.
"In the end we take full responsibility for the overall direction of the club," he said. "But one of the things that we've talked about and I think is apparent is that we need to have more depth in our minor league system."
A substantial reduction in payroll and a desire to build the prospect base are usually the hallmarks of a complete rebuild. Whether the Red Sox will go down that path is becoming one of the top storylines heading into the offseason.