CLEVELAND — Baseball connects people, moments, and generations. Fathers and daughters. Mothers and sons. If you are a true seamhead, baseball events parallel your own experiences, creating a timeline of your life. This is what’s happening as the Cleveland Indians and Chicago Cubs play out this 2016 World Series. The Tribe lead the Cubs, three games to two.

There is great anticipation over what might transpire in both cities over the next two days. As the Series resumes with Game 6 at Progressive Field Tuesday, folks in Cleveland are bracing for the possibility they’ll be celebrating the city’s first baseball championship since 1948. Meanwhile, back in Chicago, the long-suffering legions of Wrigleyville want to extend the Series to a seventh game and see the Cubs win their first championship since 1908.

It’s going to be history for one city and more heartbreak for the other.

I thought about all of this while boarding United Flight 1850 from Chicago to Cleveland on Monday. Pete Rose was sitting directly behind Aaron Boone in the first two rows of first class. As I passed Rose on the walk back to steerage, I asked him how many folks remembered his famous backup play from the 1980 World Series when they saw Anthony Rizzo save David Ross in Game 5 at Wrigley.

“Been hearing a lot about it,’’ Pete said with a grin.

Say what you want about Rose’s addiction to gambling, we all loved him as a player and he forever will be associated with big moments in the World Series. When Rose stepped to the plate in the 10th inning of the epic Game 6 at Fenway in 1975, the Reds captain turned to Red Sox catcher Carlton Fisk and said, “This is some game, isn’t it?’’ Later that night, Fisk would thrust himself into baseball folklore (and “Good Will Hunting’’) with the midnight moonshot off the foul pole, but it always stayed with Fisk that Rose had the presence to enjoy the game at its competitive zenith. The Reds ultimately prevailed in Game 7, of course, and Rose was named Series MVP, but the takeaway across the land was that Major League Baseball had won the 1975 World Series.

Baseball is winning this World Series, too. Interest is high and TV ratings are up. The Cubs and Indians managed to thrash vaunted “Sunday Night Football’’ during Game 5 at Wrigley. Having the trendy, long-suffering Cubs in the Series provides an enticing hook for casual fans, and by now it’s also clear that the Indians are worthy of the love of a sports-obsessed nation.

Which gets us back to Flight 1850 from Chicago to Cleveland. It occurred to me as I spoke to Rose that he was sitting behind the son of the man he bailed out in the 1980 World Series. That’s right. Rose was playing first base for the Phillies when Philadelphia catcher Bob Boone (dad of the man who ruined the Red Sox in 2003) camped under a popup hit by Frank White of the Kansas City Royals. When the ball bounced off Boone’s mitt, Rose snatched it up before it hit the ground. And that’s exactly what Rizzo did to save Ross in the second inning Sunday night at Wrigley.

Back in the “everyman’’ section of our flight, I encountered Stephen Murphy, longtime home clubhouse assistant at Fenway. What was Murph doing at the World Series, I wondered.

“Tito,’’ he said. “He got tickets for Pookie and me.’’

“Pookie’’ is Edward “Pookie’’ Jackson, the veteran Red Sox equipment manager. Terry Francona made a lot of friends while winning two championships for the Red Sox during his eight years at Fenway, but he was closest to the guys who do the laundry and claw the dirt out of the players’ cleats: the clubbies. Tito roadtripped with them to Mohegan Sun (picking up every tab) and five years after leaving Boston he is taking care of them now with World Series tickets that have a face value that would support a college education.

Francona knows what it’s like to break a curse. He did the job in Boston and has spent his middle-aged years receiving thanks from Red Sox fans who visited loved ones in cemeteries after the Red Sox finally won it all in 2004. Through the sheer power of his humility and humanity — coupled with some of the best-decision making in hardball history — Francona has emerged as everybody’s favorite in a World Series littered with history, droughts, and emotional rescues.

The son of longtime Tribe outfielder (the original) Tito Francona, Tito-the-manager game-planned for Game 5 in Chicago by blasting through $44 worth of room service ice cream (“They asked, ‘How many people is this order for?’ and I said, ‘One.’ ’’) When queried about carrying the burden of history for Cleveland this week, Francona answered, “I don’t feel responsible for the fact that my dad wasn’t good enough to win when he played here. Winning is hard enough . . . It’s unfair to ask this group to win for other people.’’

Good answer. But Francona knows the reality. Fair or unfair, today’s players are always playing for players and fans of past failed summers. That’s why this is such a compelling World Series. It’s a collision of historic droughts, and there’s going to be a resolution between now and Wednesday night.

Dan Shaughnessy can be reached at dshaughnessy@globe.com