Tuesday night, Roberts, now a manager, brings his Los Angeles Dodgers, seeking the franchise's first title since 1988, into Fenway for the 2018 World Series.
The Red Sox, winners of a franchise-record 108 games during the regular series, cruised to their fourth Series in 15 years (they won the first three, the last in 2013). They needed just nine games to dispose of the New York Yankees and the champion Houston Astros to continue what has been a yellow brick road.
The Dodgers, on the other hand, have survived what has been a gauntlet that started when they were 16-26 back in May. They were in third place in the National League West in September, won a 163rd game to advance to the playoffs and then beat the winners of the East (Atlanta) and Central (Milwaukee) winners to reach the promised land.
They won Game 7 on the road at Milwaukee Saturday night and will again be without home field advantage for their second straight World Series.
This is a matchup of the first- (Boston) and third-highest payrolls in baseball.
Both are deep teams and Roberts has gotten it done by playing his entire roster -- even sitting veterans like Matt Kemp, who made the All-Star team by carrying the team in the first half.
"Honestly, we have no choice but to buy into it," Matt Kemp said with a laugh during the NLDS. "We got guys on the bench that could go somewhere and play every single day and make an impact. But we're trying to win a championship, and every guy is on the same page."
"We just got so many dangerous guys in our lineup and even on the bench. So it's pretty cool to see that."
Cody Bellinger and Yasiel Puig homered and Kershaw closed out the deciding game in Milwaukee.
The Red Sox, who have won four in a row and gone 7-2 in the postseason, haven't played since last Thursday after completing a three-game sweep in Houston.
They won those three games without Sale, who started Game 1 (four innings, too many pitches) but missed his Game 5 start due to a stay in the hospital with a stomach ailment he joked (we think) was the result of a belly button ring infection. He was to have started Game 6.
"Just had a stomach thing," said Sale, who earned his first postseason win in the ALDS. "It's not fun. It's definitely not fun watching your team. Got to do what you got to do, though. It happened, we dealt with it, and we're here now. We keep rolling."
While Kershaw has never faced the Red Sox, Sale does own two career appearances -- one start -- against the Dodgers, but they were back in 2011 and '12. He allowed nine hits and seven runs and walked five in six innings.
Kershaw, who has had his postseason struggles (9-8, 4.09 ERA, lifetime), will be working on short rest but only pitched one inning (15 pitches) Saturday on his throw day. There was some speculation former Red Sox left-hander Rich Hill would start Game 1, but Kershaw makes his first Fenway start.
"I don't really think about that stuff," Kershaw said. "I appreciate the history and everything that goes along with Fenway Park. But I came here, I don't know how long ago, 2000-something, and got to at least see it, got to be here, got to appreciate the stadium and things like that."
As far as his team's journey, the left-hander said, "It doesn't matter how you get there. But to get to go back after last year is unbelievable. Where we came from this year, it's a testament to these guys, man. It's a great group. We're excited, we're gonna celebrate tonight, but we don't want to lose again, so we'll be ready to go."
Manny Machado, who quickly became a villain in the NLCS with a questionable slide at second and then a kick at the ankle of Jesus Aguilar, has also had his moments against Boston -- his 2017 slide on Dustin Pedroia injuring the second baseman's knee. It's an injury that's not fully healed as Pedroia missed all but three games this season.
Machado played nine games against the Red Sox this season before being traded to the Dodgers, batting .278 with a homer and seven RBIs. Seven of those games were at Fenway, where he hit .310 with the homer and RBIs in seven games.
In his career, he has played 95 games against Boston, batting .277 with 16 homers, 52 RBIs and a .796 OPS -- .278 with 8/32/.783 in 49 games at Fenway.
Machado is 6-for-19 (.316) with a homer against Sale, while former Minnesota Twin is 12-for-47 (.255) with three home runs against the skinny left-hander.
J.D. Martinez is 3-for-8 (.375) with a homer against Kershaw, but Eduardo Nunez is 2-for-12 (.167).
When the series shifts to Los Angles for Games 3, 4 and 5, the Red Sox will add Martinez, their DH, to the lineup in right field. That will move Betts to either centerfield -- or second base. The latter is the spot he was playing as a prospect and he has been working out there in recent days and is ready to go when called.
The Series features the first matchup of minority managers -- and Cora and Roberts are also the first managers in MLB history who both played for both World Series teams.
Red Sox knuckleballer Steven Wright, who has been out with knee surgery, could be activated for the Series.
This is the second World Series matchup between these two old franchises -- the Red Sox defeating the Brooklyn Robins 102 years ago.