CHICAGO — As much as he is enjoying this, Greg Simon cannot quite escape the thought that it might unravel in some cruel, freakish way.

He is, after all, a lifelong fan of the Chicago Cubs.

“It’s always in a small corner of your mind,” Simon, 29, said as he leaned against a wall near a concession stand at Wrigley Field, beer in hand. No sooner had those words left his mouth than Kris Bryant launched a two-run drive to left field that set a Cubs rookie record for home runs.

It was another well-timed shot in a season full of them for the most woebegone franchise in baseball.

After five consecutive losing seasons, the Cubs were nearing a playoff berth for the first time since they repeated as National League Central champions in 2008. And there is a real sense that this is the start of something big, not a short window of contention, as they try to bring home their first World Series championship since 1908 — a 107-year string of futility full of near misses, anguish and pitiful play that is the stuff of legend.