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The annual Cubs Convention is always an interesting weekend. It’s usually good for a bit of news and always worth a chuckle or two. The attendees range from the first-timer with no clue what to expect to the convention vet who perfectly sets his schedule to get every autograph and ask a question at every panel. For obvious reasons, Cubs fans are a rare breed; when the team you root for is often the butt of jokes all around the baseball world, it will naturally do some damage. But in general, the fans aren’t much different than any other team’s—some perfectly level-headed, others not so much.

I’ve attended the past four conventions, all as a member of the media, and it’s a rather exhausting three days of Cubs madness. At every convention I’ve attended, the main news has centered around the renovation of Wrigley: Introducing plans, then promising to finally start the process, and this year, with ground finally broken, explaining the contingency plan now that the bleachers won’t be open until a month-plus into the season.

But really, it’s not the news or the artists renderings that I look forward to when this weekend comes around each January. It’s the fan questions (and this year, how one person handled them so well). That’s what these three days are about—we in the media get to stick recorders in the face of managers, players, and front office members all year long, but for one day, the paying customer actually gets a chance to come up to the mic and share his deepest and darkest concerns to whoever is manning the panel (and a few hundred other Cubs Faithful in a packed convention hall). It’s a delight.

There are all sorts of questions (or comments, or rambling statements, whatever said fan feels is necessary) and below is a sampling of the best (or worst, depending on your perspective) moments. I love each equally and for different reasons, like my children. Sometimes they’re brilliant in their simplicity, and other times I have no clue what is going on and I just want to drink a beer and take a nap.

The Optimists
The first panel I attended kicked off with three comments, no questions, and quite a bit of praise for the Ricketts family and what they’ve done. Overall, the organization is in good health going forward, but keep in mind, this is a team that’s finished in fifth place for five straight seasons. They’ve had a great offseason and the future looks bright, but I couldn’t help but wonder what this event will look like when the actual major-league product is performing at a playoff-caliber level. With that in mind, this was the most well attended Cubs Con I’ve been to, and others who have been showing up for much longer than I agreed that it was more packed than they could remember. Again, this reaction just from a strong offseason, not results. But optimism is a Cubs fan’s oxygen. It’s certainly good to see them breathe again.

One of these comments was actually a prepared statement. Seriously, the fan came up to the mic and announced he had a prepared statement and the large crowd promptly groaned in unison. He went on to throw more bouquets toward ownership and the state of the organization. It was a bit rambling and prompted this reaction from me:

Honestly, the fun was just beginning.

The Absurd
There are the fans who dress up eccentrically or wear hats with dozens of trinkets pinned to them. There’s the guy who expected Joe Maddon to lay down the law and stop players from wearing Power Balance bracelets because he says they’re a scam (he’s right, but so was Maddon in saying he wasn’t going to stop his players from having superstitions that don’t harm anyone).

On Sunday, a fan came to the mic and told us all how he loves the Cubs unconditionally. “As much I love my wife and my children…” he said, before being drowned out by laughter. They weren’t being mean, it was all worth a chuckle at the start, but then things started to get, well, a bit weird. The man went on to lecture the prospects who were sitting on the panel about how they should all be grateful to be Cubs. He told them he loved them, indeed, like he loves his wife and kids. And then he told a story about his son who got a job offer from Microsoft, only to have it rescinded because of a fight he got into. He compared his son calling him that night to the way Dallas Green loved Ryne Sandberg even after an extended slump. Then, while awkwardly asking the players who their mentor was, he shared thoughts on his mentor. After they answered his question he snuck in another, while also telling us what his dreams were when he was a child (to be a broadcaster). This all happened as he was being booed for hogging the mic*.

These are the moments in my career that I live for.

*Just so people don’t think I’m being too harsh on these fans, I want to quickly share some of my most embarrassing sports-related moments. In college, I bought then-Illinois quarterback, Kurt Kittner, a beer for winning the bowl. He said ‘Thanks,’ and I walked away with a grin on my face as my friends mocked me relentlessly. About a decade ago, after the Bears lost to the Panthers in the playoffs, I yelled at my friend who was driving me home, screaming, “CHRIS THOMPSON” at the top of my lungs (if you’re a Bears fan, you’ll likely get this reference). He pulled the car over in the middle of a busy road and threatened to kick me out if I didn’t calm down. After the Cubs lost Game Seven of the 2003 NLCS, I missed about three days of work and got into numerous arguments about how everything would be all right, 2004 was THE year, and other nonsensical topics that I can’t remember because that whole week was a haze. We’re fans. We all have out over-the-top episodes.

The Insightful
Despite all the laughs and over-the-top praise, there were things to be learned and some solid questions from fans. One young high schooler asked the prospects what they’d learned from failure, eliciting some strong responses. Another fan, surely a BP reader, wanted to know what the plan was if the Cubs prospects didn’t reach their 50th percentile expectations or greater, but rather sat at the 30th percentile or perhaps worse.

But what stood out to me, beyond the delayed bleachers, ramped up expectations, and packed rooms (which could very well lead to a once-again packed Wrigley) was the clear arrival of a new star to the city of Chicago. We all know Maddon is personable; he proved it with his quote-filled, decade-long tenure in Tampa Bay and reiterated it during his introductory press conference in Chicago. But now that he’s come to a huge market, a city with a history of strong characters at the top, he has a chance to add his name to a list that includes the likes of Leo Durocher, Mike Ditka, Phil Jackson, and Ozzie Guillen. There’s been a void in that spot for the past few years, but Maddon is ready to fill it.

I knew Maddon could handle the press. He has his go-to one-liners, and regardless of the question he manages to deliver an insightful response. But at the convention, Chicago really saw how Maddon can enrapture an entire audience. He drew some of the biggest applause of the weekend and consistently had the fans laughing—and not just the ‘this famous guy made a joke, we better laugh’ kind of laughter. Maddon didn’t hesitate when asked by the panel’s host—a local radio disc jockey, Lin Brehmer—about his favorite music while young (The Rolling Stones and Bruce Springsteen).

The bespectacled manager’s repartee with the fans was impressive. When a young fan asked who would start at third, Maddon quickly turned the question around and asked who he wanted. The kid matter-of-factly stated Kris Bryant and they had a fun back and forth, with Maddon good-naturedly grilling the fan on Bryant’s abilities, before the manager delivered a thoughtful response to the question. After a bleacher bum wrapped up a question, Maddon asked if they had official t-shirts, and if so, he wanted one.

His ability to take anything thrown his way and handle it with aplomb stood out. When Brehmer quipped that most leave this job in a straitjacket, Maddon didn’t skip a beat and replied, “43 regular.” That’s what it’ll take to survive on the North Side when things get rough, and they almost inevitably will. In the recent past, whether it was a big name (Dusty Baker and Lou Piniella) or a new face (Mike Quade and Dale Sveum), the Cubs managers have left town with their reputations dinged. Both Piniella and Baker, who manned Cubs teams with huge expectations, arrived saying they were prepared for what they were about to face, but by the time they moved on, they’d admitted they hadn’t fully realized what they’d signed up for.

It’s just the reality of taking over a Cubs team with the potential to do big things. Having watched this city take apart so many, it’s hard believe anyone is immune, but Maddon may be as close as it gets. When he first arrived in Chicago he showed he could manage the media; this past weekend he proved the fans would be even easier. And the pressure, well, he embraces it—as he often says, “Never permit the pressure to exceed the pleasure.” He loves hearing his players talk about the playoffs and has repeatedly said that he’ll be talking World Series every spring. Maddon’s arrival doesn’t assure that the Cubs will finally overcome the ultimate obstacle, but it does appear that while he’s in charge, games at Wrigley will be must-attend. And by adding his presence to the quirky questioners, apparently so will the convention.

Thank you for reading

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I love this article as much as I love my wife and kids.
I love Joe Maddon's quotes as much as I love fresh hopped beer.
I think optimism is fine, but this team is full of young players who have the opportunity to be great, but are not great yet. For young players to improve, they have to play, even if it causes losses in the short run. If this team plays above .500, it's had a successful season, Period.

Yes, they could do better, and I hope they do. If they get off to a good start, they could contend. The problem I have with predicting a pennant winner is that then a 82-85 win season suddenly becomes a failure.

I also think there is a disconnect between predicting a pennant winner and keeping your best prospect in the minors for the first two months, ostensibly for business reasons. From what I've seen of him, Kris Bryant could be Rookie of the Year. Let him win the job in Spring Training. Or is that the real plan?
He wouldn't be in the minors for two months, it'd be about three weeks and could be less. They're not trying to avoid super-two status, just gain an extra year of control. Bringing him up to start the season would be an awful decision. It's broken down pretty plainly right here:
If that doesn't convince you, than I'm nothing will, we just don't see eye to eye on this topic.

As far as the Cubs competing next year, of course it'll take a lot of youth performing well. But the point is, they've upped their probability of things going well by adding established veterans, like Lester, Montero and Fowler. With them and Castro and Rizzo, they have a bit more stability and a little less reliance on unknowns. But there are still plenty of unknowns on this roster, which I've written about quite frequently.