The miracle of a modern-day Cubs fan: introducing Jimmy Greenfield

ChicagoNow community manager Jimmy Greenfield is a man of faith – in one of the most infamous teams in baseball. This commitment has dominated most of his 44-year existence, and has not been without its difficulties. The Chicago Cubs’ franchise has tried Greenfield’s patience, loyalty and enthusiasm for decades, and has produced a wealth of memories shared by friends, family and colleagues alike.

“During the 1984 Cubs’ season, the Cubs blew a lead and Jimmy got so angry he kicked the wall in our family room,” Jimmy’s brother, Bobby, said. “His foot went right through it.”

Greenfield’s love-hate relationship with the team recently culminated in a 256-page book published last month: “100 Things Cubs Fans Should Know and Do Before They Die.”

“Nothing compares to the book launch party,” Greenfield said. “When the first box of books came in, my sons were like, ‘Dad, did you write all those books?’ Having my parents, family, friends and colleagues all together – that was definitely my favorite part.”

Greenfield’s love of sports and writing has led him to a variety of positions in Chicago’s journalism market. After graduating from the University of Kansas with a journalism degree, Greenfield began his professional career answering phones at the Tribune’s high school sports desk. Before long, he found himself covering both Cubs and White Sox baseball for the Tribune with an opportunity to meet both Bill Murray and Sammy Sosa at Wrigley while covering a tiebreaker playoff game.

“Murray was in the press box to sing the 7th inning stretch and I said to him, ‘So, you’re singing the 7th inning stretch – what song have you selected to sing?’ and I got a laugh out of him,” Greenfield said. “I’ll never forget that – making him laugh for a split second.”

Moments later, the Cubs won the game and Greenfield found himself jogging on the field with Sammy Sosa.

“When the Cubs won, it was an explosion of excitement,” Greenfield said. “They let the reporters run onto the field and I ended up running next to Sammy Sosa carrying my microphone recording him. That was wild.”

Greenfield has gotten a chuckle out of more than Bill Murray. According to Chris Malcolm, Greenfield’s former colleague at Chicago RedEye, Greenfield’s innovative ideas have always been ‘refreshing’ in the newsroom.

“Jimmy comes up with some really fresh and original ideas,” Malcolm said. “He covered a Bears playoff game once with the task to ‘get something painted on him,’ and he came back with a photo of him having a Bears fan write ‘Go Bears’ on his cheek using a ketchup packet from the concession stand. Who thinks like that? Jimmy does.”

Sports have always been an anchor in Jimmy’s life, but brother Bobby insists there is more to Jimmy than baseballs and hockey pucks.

“Jimmy has always been thought of as a sports guy, but he’s not one dimensional,” Bobby said. “It’s true he is a sports nut, but he has friends who don’t care at all about sports – he gets along with everybody.  He’s an all-around guy’s guy. And he doesn’t seem to kick walls in anymore.”

In closing, there is one word of advice Jimmy would like to give to Cubs fans nationwide:


While you’re waiting, check out this epic video that Jimmy says is his “claim to fame:”

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