Wrigley Fields

2008: Age 7 | Ross Dettman for ESPN

2016: Age 15 | Alyssa Schukar for ESPN

As Cubs catcher Miguel Montero rounded the bases after his pinch-hit grand slam in Game 1 of the NLCS, Wrigley Fields sat in his bedroom and played video games, somewhat annoyed at all the noise his parents were making in the living room as they watched the game. The boy was named after one of the most iconic stadiums in the world, but he's not that big of a baseball fan.

"It's just kind of slow and boring. I can't sit still that long," said Fields, a freshman at Lockport High School in Chicago's southwest suburbs. "I keep up with the team. I know if they've won or lost. With my name, I have no choice. But it's not like I'm some rabid fan who lives on every pitch. That's my dad. For me, school, diving and video games. That's my life."

Still, Fields loves his name. He chuckles when a substitute teacher stumbles during roll call or when his name is announced at a diving meet and parents look around in disbelief. Sure, kids might tease him occasionally, but with his laid-back personality, he couldn't care less.

"I've never had a day where I haven't liked it," he said. "People learning my name for the first time is honestly the best part of my day. It's the best ice breaker. And then people try to talk to me about the game, and I just play it off like I know what they're talking about."

Wrigley's mom, Kathy, who agreed to let her husband, Jerry, name their first boy after the stadium, has similarly grown to love it.

"He's just Wrigley," she said. "I don't even think of him associated with the stadium most of the time. It's a name that is as unique as he is."

As for the World Series, Wrigley says he'll be watching. Sort of. He did manage to come out of his room when the Cubs were two outs away from winning the pennant.

"I know how big of a deal this would be," he says. "I hope they do it."

Anna Patras

2008: Age 16 | Ross Dettman for ESPN

2016: Age 24 | Alyssa Schukar for ESPN

To say that Anna Patras is still as passionate about the Cubs as she was in high school would be an understatement. During the 2015 playoffs she nearly lost her administrative assistant job as she traveled back and forth from Minneapolis for as many games as she could, often taking 6 a.m., morning-after-the-game flights to be at her desk by 8. "Looking back on it now, probably not the wisest of decisions," she said. "But I can get blinded sometimes by all things Cubs."

The 2016 run has been far better for her career, considering she received a promotion and transferred this past summer to her company's Chicago office. Still, she has friends who don't always get it when she drops everything - and, if needed, anyone -- to be in Wrigley or at a Wrigley pub to watch the playoffs. "To me, it's about the game, and that doesn't always sit well with everyone," she says. "And if I have a ticket -- even a single -- well, I'm going to go."

Patras has also used her Cubs passion to raise more than $6,000 for esophageal cancer research at the Mayo Clinic. The disease took both her uncle and the father of her best friend. During last year's playoffs, she ran a half-marathon in a goat costume to raise donations, and this year, when she won the Cubs lottery for playoff tickets, she auctioned off a ticket to NLDS Game 2 with proceeds going to the Mayo Clinic. She plans to watch every game of the World Series in Wrigleyville, except one, which she will watch on the couch next to her grandmother, who is 81.

"Her and I are long overdue to watch the World Series together," she said. "I can't wait."

Kurt Evans

2008: Age 29 | Ross Dettman for ESPN

2016: Age 36 | Finn O'Hara for ESPN

Eight years ago, as the founder and writer for Cubs blog Goat Riders of the Apocalypse, Kurt Evans knew without question that the greatest moment of his life would come when the Cubs eventually won the World Series. But then in 2010 he left his high-pressure sales job to become a teacher. His creative energy for the blog dwindled as he focused on the classroom. Four years later, he and his wife welcomed their first son into the world. And now everything has changed.

"I was totally wrong," Evans said. "Becoming a dad will be the greatest thing that ever happened to me."

Evans still follows the team closely, especially since Tom Ricketts bought the team and in 2011 brought in Theo Epstein to run the baseball operations department.

"If you think about it, the real, true curse -- if there ever was a curse -- is the curse of bad ownership," Evans said. "It's pretty obvious that's what held this team back for so long."

The morning after the Cubs won the NLCS, the Toronto resident connected with old Cubs friends and devoured as many Cubs stories as he could find. And he thought about his son, who won't have much of a choice in choosing a favorite baseball team.

"He's going to have a completely different Cubs experience than the one I had," Evans said. "He's going to grow up with a Cubs team that is likely to be competitive and interesting every year. And could maybe even win multiple World Series. It's strange just to say that. But it couldn't make me any happier."

David Diaz

2008: Age 32 | Ross Dettman for ESPN

2016: Age 40 | Alyssa Schukar for ESPN

In the top of the ninth inning in Game 1 of the NLCS, former WBC world champion David Diaz crossed his arms and legs in his bed and refused to move, hoping to spark some sort of rally in a game in which the Cubs and Dodgers were tied 3-3. And when three Cubs reached base and Miguel Montero hit a grand slam, Diaz didn't budge until the game was over.

"My wife tried to take my hand, and I'm like, 'Leave me alone!'" Diaz said. "I didn't move or say anything else until the game was over. And then when the Cubs won I finally told her, 'I thought it was me. I was the one making all this happen.'

"It's crazy, I know. But that's me and the Cubs -- anything I feel I can do to help."

Diaz retired from boxing in 2011 and now works as a real estate agent in Chicago and trains youth fighters. He's as passionate -- and superstitious -- about the Cubs as ever. Just as he was in 2008 when he was asked to enter a prefight press conference with Manny Pacquiao alongside a goat. "I was like, 'no way,'" Diaz said. "I can't be associated with some goat."

Diaz, whose Realty of Chicago office is on the city's South Side, doesn't mince words about his goal for the 2016 Cubs team: "I want the World Series. We want that belt. I'm happy the Cubs are doing great, but the ultimate prize is to finish No. 1. And then when it is over, go out and do it again next year. Now that would be something to shut everybody up from the South Side."

Billy Corgan

2008: Age 41 | Ross Dettman for ESPN

2016: Age 49

Smashing Pumpkins frontman Billy Corgan politely declined a request to talk about his Cubs fandom, suggesting he did not want to grant any Cubs-related interviews until after the World Series. But Corgan has been seen during the playoffs at Harry Caray's restaurant and at Wrigley Field.

Dr. Jordan Grafman

2016: Age 65 | Alyssa Schukar for ESPN

It's been almost a decade since Dr. Jordan Grafman penned a chapter in the book "Your Brain on Cubs," and yet, despite his renowned work as the director of brain injury research at the Rehabilitation Institute of Chicago, his lifelong love for the Cubs is still one of the things that brings him nationwide notoriety. He's quoted regularly by George Will, and this October, the interest has come in the form of interview requests. Reporters from all over the country are eager to listen to Grafman explain how the brain of the Cubs fan is intellectually superior to that of any other team because of the mental gymnastics it takes to support a perennial loser.

"It's not like this is going to help my career or anything, but to be a fan about something since you were young and have all these people ask your advice is kind of fun," Grafman said.

Although Grafman's love for the Cubs hasn't waned, he's learned to no longer be driven by bottom-line results. He says he doesn't care if the team wins the World Series. And he isn't kidding.

"I know people are going to look twice at that, but this team is so much fun to watch. I take so much joy in watching Javy [Baez] and [Jorge] Soler and the younger guys. I just want to see them play longer and longer. Of course, if they play longer than anyone else, there's a good chance that means they will win it all. But to me that isn't everything."

Ronnie 'Woo-Woo' Wickers

2008: Age 67 | Ross Dettman for ESPN

2016: Age 75 | Alyssa Schukar for ESPN

There was a time when Ronnie Woo-Woo couldn't sit still at Wrigley Field. When the most polarizing Cubs fan would spend games scampering up and down the cement bleachers, "wooing" all along the way. But those days are long gone. Wickers fell at Wrigley on July 19, tearing the patellar tendon off of his kneecap, prompting surgery and a lengthy rehab that caused him to miss all but the last two games of the regular season. And even then, on subsequent trips to Wrigley, he's worn a bulky knee brace and needed a walker to get around.

"It was the first time I've ever seen him at Wrigley Field where you could see that sort of sadness on his face a bit," said his longtime friend Janet Tabit. "He used to be the one running up and down those stairs cheering all the time. And that day we had to move to a different part of the ballpark where he could be more comfortable. And you could tell it bothered him."

Just as frustrating in recent years has been the fading of Wickers' voice. Doctors have looked at his throat and vocal chords and determined nothing is wrong. But the wear and tear of a half-century of "wooing" for the Cubs has prompted his voice to come and go.

"I try to get past it," Wickers said. "People ask me to cheer, I give them a 'woo.' Sometimes it's still there. But I promise if they win the World Series, it will come back again. This team is in it to win it. And when they do, that's all the medicine I will need."

Bruce Ladd

2008: Age 72 | Phil Ellsworth for ESPN

2016: Age 80 | Justin Cook for ESPN

When told this October that he is the oldest living cast member from ESPN's original No Love Lost feature in 2008, Bruce Ladd responded with his typical honest, frank tone. "Hot damn," Ladd joked. "My mother always told me I should accomplish something respectable in my life."

The former Washington, D.C., lobbyist confessed earlier this year that his motivation in starting a Beltway-centric Cubs fan club, called the Emil Verban Society, was based not on his love for the team but rather his desire to grow his Rolodex and open some doors in Washington. "It did wonders for me," he said. By the time he stopped sending club newsletters and put the operation on a permanent hiatus in 2010, Hillary Clinton, Barack Obama, Dick Cheney and Antonin Scalia were all members.

Ladd, now 80 and retired in North Carolina, has battled 30 years of heart disease and multiple melanomas. Now he says his kidneys are giving him trouble. And he's learned over the years not to expect too much from his favorite baseball team. Not even this year.

"I know the answer should be, 'Oh yes, we are going to win the World Series.' But honestly, my expectations were lowered a long time ago," he said. "I'm not looking to win the World Series this year. Why would I possibly think that? There is 108 years of history saying that isn't going to happen.

"The number of times we have been in the playoffs the last 20 years? If you look at it, honestly, it's just more false hope. The Cubs love it. The fans love it. It's good for the bottom line. But honestly I don't have any expectations."

Betty Maute

2008: Age 84 | Ross Dettman for ESPN

2016: Family of Betty Maute | Alyssa Schukar for ESPN

On the night the Cubs won the National League pennant, all three of Betty Maute's children, six of her seven grandchildren and all six of her great-grandchildren gathered together to watch the game. Just the way she would have wanted it. Grandson Brian Maute, who attended a Cubs game with his grandma every summer from the time he was 4 years old until she died, wore the "Betty #7" jersey she used to wear all the time. And when the Cubs turned the final 6-4-3 double play to beat the Dodgers, it was understandably emotional.

"There were a few tears in the room, of course," Brian said. "The Cubs were such a big part of her life. She's the matriarch of why we all became big Cubs fans. And we just couldn't help but think how she would have been so super-excited. On absolute cloud nine."

Before Betty died in 2014, her grandson says she was excited about the hiring of Theo Epstein and the direction the club was headed.

"Of course, we'd love it for her to be here to see this - she would have adored this team and the way they play and carry themselves," Brian said. "But she had 90 years of Cubs fandom in her life. It was a great life. So it's hard to be too upset. We will just have to celebrate for her."

Helen Keiling

2008: Age 93 | Ross Dettman for ESPN

With each Cubs victory during the playoffs, Leslie Keiling hasn't found herself smiling. Her mother, Helen, died in 2010, but she was such a fanatical Cubs fan that when she was alive, Leslie would read her the Cubs articles in the newspaper each morning.

"We've said it so many times this year," Leslie said. "When they nailed the division, when they beat the Giants and then the Dodgers. If only Mom was here. If only Dad was here. We're far from the only ones. That's what this is about for so many people. We have a grandma or someone wishing they could see this team."

The 2016 Cubs, Leslie says, would have been one of her mother's favorites.
"She hated all the showboaters like Sammy Sosa," Leslie said. "But this team, they are such gentlemen. Everyone who knows my mom always says that -- she would have loved these guys. Like the way [Anthony] Rizzo apologized to the umpire in Los Angeles? She would have been so giddy about what they've done and the gentlemen they are."

Richard Savage

2008: Age 100 | Ross Dettman for ESPN

Richard Savage photographed in 2008 in Chicago, Ill. He died in 2013 at age 105.

Andrew Hancock

After 107 seasons and more than 15,000 games there is no fan base that has ever been more tortured. The question is whether or not this is the year it finally comes to an end. Far less for the hyper teenagers or always believing die-hards in their 20s and 30s and more so for their parents, grandparents and great parents. For loving the Cubs is something that is passed down from one generation to the next, with the promise to never give up. Because someday, it will happen.