Judith Sherwin throws up a ball signed by the baseball players she coached when they won the Warren Park Championship; her son, Jason, was 13 at the time. Credit: Stephanie Bassos

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.

I met Sherwin when I was five years old, after her only son, Jason, kicked me in the face. It was an accident, but his foot to my kisser knocked out the first tooth I ever lost. Jason and I became fast friends. There were many weekends when I’d sleep over at the Sherwins’ place, and it was there and on frequent car rides to sports games and birthday parties and McDonald’s that I learned about the Cubs. The words coming out of Sherwin’s mouth were fascinating: “Bullshit!” “Are you fucking blind?!” and of course, “Fucking moron!” Sherwin says “fucking moron” often, especially when she’s watching the Cubs. On some level, the Cubs taught me how to swear.

In the summertime she’d take Jason and me to Wrigley Field, where she’s been a season- ticket holder since 1985. We’d go early, right when the park opened, and try to get autographs from the players. It was the first time I’d ever had mustard on a hot dog. I learned about Harry Caray, Gary “Fatty” Gaetti, the gloriously named Paul Assenmacher. In January or February, Sherwin would let me tag along for the Cubs conventions, where Jason and I would buy baseball cards or get autographs from Ron Santo. I quickly understood, via Sherwin, that the Cubs were bad, had always been bad, and would probably always be bad. I’d been told that the Cubs winning the World Series was so unlikely Chicago would probably burn to the ground if it ever happened.

Yet here we are: 2016. The Cubs more than ever appear to be on their way to breaking their title drought, now 108 years running. They aren’t just in first place in their division, or in the National League—at the time of this writing, they have the best record in baseball. Over at FiveThirtyEight, writer Rob Arthur crunched the numbers and proclaimed, “This Year’s Cubs Might Be Better Than the Incredible ’27 Yankees,” often referred to as the best team in baseball history.

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 has an astonishing recall of Cubs history. She remembers virtually all the players and managers, even the details of many regular-season games. And don’t get her started on the 1969 Cubs.

“I mean, I can’t even tell you,” Sherwin says, sounding newly traumatized. She has shoulder-length sandy blond hair that’s often covered by a blue Cubs cap, on the back of which is embroidered season ticket holder 20+ years. “It was . . . It was unbelievable,” she says of the ’69 season. She leans in and her voice drops. “They had an infield that had been together for a few years. Santo, Kessinger, Glenn Beckert, and Ernie Banks, if you were to go from third to first. And everything was just gorgeous. And I think it was, like, on the fifth of August they had an eight-game lead over whoever was in second place. Oh, it was awful. I mean, I can’t tell you how miserable that was, because it was like a slow drip. It was torture. And it went on for like a month and a half. And you kept thinking, they’re not really gonna blow this, are they? And they were doing it! And it was like they just died. It was just the worst.”

Taken together, her memories of Cubs baseball constitute a monumental archive of dejection. But with the team playing at such a historically high level, this could be the year, the year they turn it all around, the year Judith Sherwin finally gets to see the Cubs play in—hell, maybe even win—the World Series.

I asked her if she’s concerned about a repeat of the agony of 1969, worried that they might blow it once again. “I don’t know if ‘blow it’ is the right way to look at it,” she says. “I would like to see them in the World Series. I’d love to see them win the World Series. But the truth is I won’t love them any more if they do.”

Sherwin surrounded by other Chicago sports memorabilia
Sherwin surrounded by other Chicago sports memorabiliaCredit: Stephanie Bassos

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.

“They played the Cleveland Indians and they lost,” Sherwin says. “I don’t remember the score. My memories of it were the vendors and how green the field was.”

In those days, WGN carried all the local baseball games. “In black and white, obviously,” Sherwin points out. She’d watch both the White Sox and Cubs whenever they were on, but pinpoints her preference for the north- siders to a game against Hank Aaron and the Milwaukee Braves in 1958.

“I had started watching the first inning. I left the house, I went to the library. I came back and the Cubs were losing seven to nothing. And it was the sixth inning. And then the Cubs scored seven runs and eventually won that ballgame eight to seven,” she says. “So if I wasn’t hooked on the Cubs before, I was definitely hooked on the Cubs by then.”

Sherwin lived with her mother, a legal secretary, and her grandmother, who was on social security. When she was 11 the family moved to Lakeview, and in the summertime her grandmother would give her money to ride the streetcars. Sherwin would invariably go to Wrigley Field whenever the Cubs were in town. She was able to take advantage of a policy that Wrigley Field promoted at the time. “They would let kids into the ballpark after the sixth inning, for free,” she says. “If you came to the game, you got in for free if you picked up a few rows of seats.”

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.”

At Lake View High School, she befriended a girl who would often join her at Wrigley Field for Ladies’ Day, the Cubs organization’s attempt to market baseball to women. Sherwin and her friend would go “after the games and get autographs and hang around and do all that sort of stuff,” she says. “I was madly in love with a player named Richie Ashburn who was on the Phillies. And he got traded to the Cubs. That was like heaven.”

Sherwin attended Roosevelt University on a scholarship and majored in psychology, though she was equally involved with the local theater and improv communities. “A lot of the Chicago theater people are big Cub fans,” she says. “It’s because they work all night and they sit in the ballpark all day. I used to do that too. You know, I’ve spent a lot of time at Wrigley Field.”

In 1972, Sherwin married Byron L. Sherwin, a rabbi she’d known since the previous year, when they were set up by another rabbi. “Byron was never a big one for the ballpark,” she’s quick to point out. The rabbi, in general, wasn’t the athletic type. My memory is of him sitting in a chair, smoking Schimmelpenninck cigarillos, reading or writing or cracking jokes. But Byron was hardly idle—in fact, he was brilliant. He had a PhD from the University of Chicago, was a protege of Jewish scholar Abraham Joshua Heschel, and was a member of the faculty of the Spertus Institute, where he was also the dean and vice president for nearly 30 years. Byron, a native New Yorker, referred to the Cubs as “Little League.” They weren’t the Yankees. On the few occasions when he would indulge his wife and accompany her to the ballpark, he’d bring a book to read.

“The Cubs were down two to nothing, the bases loaded, and Dave Rader came up and hit a double, and the Cubs won the ballgame,” Sherwin recalls. “And Byron read his book all the way through the whole thing. I was losing my mind, and he’s, you know, sitting there, reading a book about something or other.”

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.

A clipping from a <i>Tribune</i> article about <i>The Cubs and the Kabbalist</i>
A clipping from a Tribune article about The Cubs and the KabbalistCredit: Stephanie Bassos

Though Byron’s fascination with the Kabbalah and Jewish mysticism is evident in The Cubs and the Kabbalist, I wonder if he was dubious of the existence of miracles. Judith Sherwin is undoubtedly a skeptic, especially when it comes to the Cubs. “The [Curse of the] Billy Goat—it’s all a bunch of bullshit,” she says. “I mean, you either play the games or you don’t play the games, you either know what you’re doing or you don’t. This is madness. Forget all the crap, focus on what you’re doing right now: right now what you’re doing is you’re playing a baseball game.”

Last May, Rabbi Sherwin died at the age of 69 after a long illness. In remarks made during a memorial lecture this past spring, Rabbi Elliot Cosgrove paid tribute to his former teacher, saying that “The depth and range of Byron’s knowledge reflects a set of circumstances that would be difficult, if not impossible to replicate. The tensions that came to be crystallized in him, those still resonating are, on some level, representative of a bygone era.”

And in a sense, Judith Sherwin is also representative of a bygone era, a more pure period that existed before baseball at Wrigley Field became “a business,” as she often says, derisively.

“Wrigleyville has changed a lot,” she says. “Santo was broadcasting the game and there was some craziness going on in the stands, and he said, ‘You know, there are a lot of new Cubs fans, and they don’t really know how to behave.’ 

“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.

Sherwin has had the same seats since 1990, in the grandstand directly behind home plate, in the middle of a row so she doesn’t have to get up when people go to the bathroom. She got her tickets after writing a letter to Frank Maloney, the former ticket operations manager for the Cubs, in which she described the view from her prior location, conveniently positioned behind a giant metal beam. He was so amused by the letter that the following January, he welcomed her to an empty Wrigley Field and invited her to pick any seats she wanted in the park.

“The place I sit, those people, we’ve all been sitting there together for 25 years,” she says. “And it’s nice to come every year and see people that are still here. One lady died a couple years ago; her husband is now remarried. The guy who sits behind me, I think he’s retired now, he’s a math professor at U. of I. So you see people you know. They’ve seen Jason grow up. I like that.”

Last fall, when the Cubs were down two games to none in the National League Championship Series against the Mets, Sherwin didn’t appear worried. She was relaxed, eating a bagel and cream cheese at a River North cafe before heading home to change into Cubs gear. That night she’d be at Wrigley Field for game three, in which the Mets beat her team 5-2. I asked if all the decades of Cubs baseball had made her accustomed to failure, desensitized to disappointment. But that wasn’t it. She was delighted by the team. She said it felt like a tide had turned, that eventually this squad would find a way to get it done.

“Some people feel it would be terrible if the Cubs win the World Series,” she said, referring to a peculiar subset of longtime fans who think that a championship would sour the storied tradition of the “Lovable Losers.” “I don’t think it’d be terrible. But I don’t necessarily care. If they don’t, I still love them—they’re my team. I really hope they do it. But the sun will rise again afterwards, and that’s the great thing about baseball, you know? I start counting again. When the season is finally over, I sit down and I figure out how many days there are until opening day. And opening day comes again and the world begins again.”  v

Sherwin demonstrates the grip for a two-seam fastball with a baseball from the final Little League team she coached. "Depending on where your thumb is on the bottom will control how it breaks," she says.
Sherwin demonstrates the grip for a two-seam fastball with a baseball from the final Little League team she coached. “Depending on where your thumb is on the bottom will control how it breaks,” she says.Credit: Stephanie Bassos