If the roots of Jewish humor are anger and disappointment, then the Chicago Cubs may be the funniest, most Semitic team in sports history. This helps to explain why Judith Sherwin is such a big Cubs fan. The 71-year-old attorney’s Rogers Park apartment and her Loop office are filled with Cubs memorabilia: a baseball signed by Ernie Banks, a jersey autographed by Sammy Sosa, Cubs teddy bears and other charms intended to help the team win.

Of course, if you’re a Cubs fan, you’re not entirely overjoyed by the hype. The Cubs, after all, are the kings of choking under the strain of such lofty expectations. And few people know the pain wrought by the team more intimately than Sherwin. Having regularly attended Cubs games for nearly 60 years, she’s witnessed quite a few collapses.

Sherwin’s earliest baseball experience didn’t involve the Cubs. Her uncle Seymour, who lived with her family in Albany Park until she was six, was a baseball fan and took Sherwin to her first game in 1952, the White Sox at Comiskey Park.

Being a young girl who was into baseball wasn’t always easy. “Girls in those days did not play baseball,” Sherwin says. “But I played, you know, with kids in the neighborhood. And I always loved it.”

Books were Byron’s Cubs. He was a voracious reader and prolific writer. He had an enormous library, ranging from scholarly Jewish texts to 19th-century philosophy to Russian literature, and he wrote or edited more than two dozen books. In Byron’s only novel, The Cubs and the Kabbalist, published in 2006, the narrative is semi- autobiographical: Rabbi Jay Loeb is convinced that his wife, an attorney, is having an affair, when in fact her infatuation is with the Cubs. To win back her affections, Rabbi Loeb performs a Kabbalistic ritual on the pitchers’ mound at Wrigley Field to remove the Curse of the Billy Goat, inventing a golem that will help the Cubs win the World Series. Yet the story is really about how most people underestimate the powerful effect that miracles have on a religious follower’s devotion.

“Whenever the Cubs are doing well, it’s a wonderful thing—except it brings a lot of people into the ballpark who don’t really know how to behave. There is an open-bar kind of feeling sometimes in the ballpark,” she says, knocking the overconsumption of alcohol and the rowdiness that sometimes results.