Hillary Clinton and the Chicago Cubs: It's complicated

Hillary Clinton, a lifelong Cubs fan, celebrated Saturday night when Chicago's long-cursed baseball team won a spot in the World Series for the first time in 71 years.

But her relationship with the Cubbies -- well, it's complicated.

The former secretary of state may have gone to Cubs games with her father as a kid, but after leaving Illinois -- and around the same time she ran for Senate in New York -- the former first lady touted her love for the New York Yankees, too.

In 1999, Clinton donned a Yankees hat after the team visited the White House to be honored for their 1998 World Series win. Photos of Clinton, who was preparing her Senate run, were slammed as brazen political pandering.

One Yankees fan in particular -- former New York Mayor Rudy Giuliani -- knocked Clinton for her 1999 Yankees allegiance. In an ironic twist, however, Giuliani pledged his support for Yankee arch rivals the Boston Red Sox during the 2007 World Series.

Why? It might have been that Giuliani was running for president and all-important New Hampshire is in the heart of Red Sox nation. Or, perhaps it was as Giuliani said at the time, he just wanted to support the American League team. Maybe.

Clinton has explained her dual allegiance as the result of loving baseball, but needing to pull for a winner.

In a 1996 op-ed, Clinton wrote that her Cubs support was a "family affair," where her father and bothers would "act out plays that had just happened and yell and scream and imitate announcer Jack Brickhouse."

In 2003, Clinton wrote: "In our neighborhood, it was nearly sacrilegious to cheer for the rival White Sox of the American League, so I adopted the Yankees as my AL team, in part because I loved Mickey Mantle," Clinton said in her memoir "Living History." "My explanations of Chicago sports rivalries fell on deaf ears during my Senate campaign years later, when skeptical New Yorkers were incredulous that a Chicago native could claim youthful allegiance to a team from the Bronx."

But it was during a speech to the Economic Club of Chicago on October 8, 2014, where Clinton explained most clearly her dual fandom: A Cubs fan by birth and a Yankees fan because she likes winning.

"I am Cubs fan," Clinton said, arguing that being a fan of the often losing baseball team prepared her for life. "And when I was a little girl, I quickly caught on that being a Cubs fan was being more of a tenant of religious faith than any kind of passing fancy."

But she later in the question and answer, Clinton spoke about becoming a Yankees fan.

"I couldn't stay hitched with a losing team ... I had to search for a team that would counterbalance the experience of losing every single year, so -- I hate to say this, and I know you'll boo me -- I became a Yankees fan," she had said. "I alternated my affections because it was just too hard being a Cubs fan, only being a Cubs fan."

"Someday," Clinton said wistfully, "someday, it will happen."

But this time around, something finally clicked for the Cubs -- and Clinton has heard about it on the campaign trail. Even before the season began, she was signing Cubs jerseys, joking about this (finally) being "the year." She even headlined a fundraiser hosted by a co-owner of the team.

"Wouldn't it be wonderful? Unbelievable, but wonderful," Clinton said of the prospect of a World Series run a year ago in Iowa, after a Cubs fan asked her to sign his jersey.

Rooting for the Cubs makes you a "very patient person" and shows you "can't expect things to turn out as you wish them to be," she told the man.

"Thanks for wearing that," she said. "It gets my blood going."

A few weeks later a man wore a custom Cubs jersey that had Clinton and the Number 45 on the back, in honor of the prospect she would become the 45th president.

Clinton signed the jersey and told the supporter that 2016 was the year both she and the Cubs would win.

So when Connolly Keigher, Clinton's trip director presented her boss with her phone to stream the post-game celebrations from Wrigley field on Saturday night, the former Illinois native looked elated. Photos of her reaction show Clinton making a face of astonishment and reporters saw Clinton laughing and joking with aides as she watched.

Brian Fallon, Clinton spokesman, said Sunday that Clinton has already asked her staff to make time to watch the World Series.

As for if she will go, Fallon only offered a "We'll see."

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