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An unconventional Cubs Convention: Fans, friendship and love for a baseball team

A summary of happenings at the first Cubs Con in three years.

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I am a part of the greatest community in the world: I am a Cubs fan. Cubs fans can be from anywhere and can be anyone. You can be a part of any religion, race, or gender and the bond that ties us all together is a love of the Chicago Cubs. Whether you’re an autograph hound, a fantasy league stats nerd, gear head, or inebriated bleacher bum karaoke singer, there is a place for you at Cubs Convention.

We all came back to the Sheraton Grand in downtown Chicago after what seems like the longest two years of our lives. For the Cubs Con veteran, the familiar sights, sounds and happenings were a welcome sight for sore souls as the January event is perfectly timed between the Winter holidays and Pitchers and Catchers. In the bleakest part of winter, we can cheer our boys of summer. To hear the Lowrey organ played in the center of the hotel lobby by my friends John Benedeck and Josh Langhoff is to be reminded that there is a warm beautiful summer ahead and another season in the sun for our boys in blue. It was good to be back. To be back with all of you wonderful Cubs fans I’ve met over the years.

In the past, when covering the Cubs Convention for BCB, I would snap thousands of pictures and write down everything I found interesting or informative from the panels, and post three or four separate stories about my personal experience. This year, with the Con being televised by Marquee Sports Network, there was no urgency to report on what was being reported by the actual reporters like Cole Wright at Marquee. So, if you’re looking for Cubs news about the Convention you can just watch it! What I’m here to write about is my experience hanging out with the incredible Cubs fans and employees that I’ve come to know over the past decade.

It’s a conversation I had late Friday night with my friend Evan Altman from Cubs Insider as we downed a couple shots of Malört paid for by my friend Corey Furlong who had Venmo’d me $100 to buy a few rounds at Lizzie McNeils at the bloggers hangout. I had shown up to Lizzies fashionably late after singing Harry Karaoke with my friend and Bleacher Bum Band bandmate Bleacher Jeff, Cubs announcer Jeremiah Paprocki, and the Spanish voice of the Cubs and Elvis impersonator, Miguel Esparza. John Benedeck was the ringer singer in case nobody wanted to perform in the center of the Sheraton lobby. John sings as well as he plays the organ! In fact, I hung out with Miguel, Jeremiah, Jeff and John most of Friday evening, bumming beers off Cubs fans who had the foresight to bring their own coolers to wheel around the convention. People kept stopping to take photos with all of us. I felt like I was part of the old Frank Sinatra lead Rat Pack. So many people recognized me from The Son Ranto Show, my work on this site, and my ridiculous Wrigley Field weather reports. People told me they enjoy my Twitter and parody songs, even singing some of my own lyrics back to me! Even though, I am no longer as young and handsome as Jeremiah, everyone’s kind words and appreciation of my work made this aging rocker feel like a million bucks. There, surrounded by some of the best in the business, feeling like I belonged to something greater. Feeling the love of the Cubs fan community that I also dearly love.

A side anecdote about coolers. When the doors are opened for Opening Ceremonies there is a rushing flood of humanity to the front row that makes any Black Friday stampede look like a cake walk. After securing your seat, you have to sit and wait for over an hour until the event begins. My friend and fellow podcaster, Fly the W’s Crawly always gets front row center. Always. To where he always orders a pizza and always has a cooler for me to sit on when I show up five minutes before the show starts. When Tom Ricketts was introduced, Crawly and I leaped screaming to our feet, drowning out the smattering of boos Tom received. Crawly and I have been around Tom so many times at this point and he knows us. We’ve had beers together at my friend Stewart McVicar’s Club 400 where I watched Tom sign a wall and drip gold pen ink all over the floor. We wanted to make him feel welcomed at his very own convention, so we jumped up and cheered. When the applause subsided and it was time to sit back down, I attempted to do so and failed miserably. My butt hit the edge of the wheeled cooler sending it flying into the legs of the lady behind me and sending me to the floor with my legs in the air and a bruised tailbone and ego. This was the sight in front of Tom Ricketts as he began his speech welcoming Cubs fans to the convention. Too bad Marquee didn’t catch that on video. My detractors and fans would both have had a field day with the footage.

The Opening Ceremonies were pretty much the same as they always were. Former and current Cubs players and coaches walked across the stage slapping high fives with kids in front of the stage. My favorite moment was when Cubs Anthem singer, the legendary Wayne Messmer asked us all to imagine a beautiful day game at Wrigley Field, the sun is shining, the skies are blue, the wind is blowing out and the Cubs are absolutely torching the Cardinals. Everyone in that ballroom knows exactly what that day feels like, and I told Wayne later in the evening when we were hanging out in the lobby by the organ that I could feel everyone’s collective imaginations create that moment together. It felt real. He said he could feel that too and then sang some off-color lyrics I wrote about the Cardinals in a Clash parody I wrote, that he saw Bleacher Bum Band perform on a rooftop at a Patrick Wisdom event last summer with Club 400. We both laughed and I told him not to get himself canceled like I always try to do.

The party at Lizzies Friday night had gone on a few hours before I had arrived with the Malört shot money, so the Bleacher Nation, CHGO, Cubs Insider, Athletic, Bleed Cubbie Blue and the Twitter personalities and independent writers were already torn up when I entered. Shots of Malört have a way of clouding your memory while unnecessarily extending a long evening, but it was nice to give everyone a hug as we all embark on another campaign covering our favorite team. We are so incredibly lucky as Cubs fans to have dozens of independent voices so passionate about the team we love. I’ve become great friends with all of them over the decade plus I’ve been producing Son Ranto and reading just about everything they write, so the night sort of slipped away and by the time I stumbled out of Lizzie’s after 2 a.m., Ubers were surge priced, so I started walking north hoping they would come down. They didn’t, so I ended up just getting on a bus to the red line. It was all a mistake as it took forever and I should have just sucked it up and paid the $40 it would have taken to get home in 15 minutes. When I finally got home, I knew I wouldn’t make the Ricketts Family Forum which started only a few hours later at 9 a.m. I couldn’t face Tom after he saw me fall off the cooler anyway.

Saturday morning, I woke up at 9:30, opened Twitter and immediately saw video of the aforementioned Crawly asking a question to the Ricketts about the new sports book at Wrigley and whether the income generated will show up on the Cubs roster. He made mention of Mets owner Steve Cohen who has blown through luxury tax tiers in an effort to buy a championship team. I had seen Crawly last at Lizzie’s and could tell he had gotten a few hours less sleep then I had. His voice was like sandpaper and his Cubs hat was tilted off to the side looked as if it had been slept in. Crawly confirmed this for me when I finally showed up with Bleacher Jeff to see the live taping of Ian Happ’s podcast at noon. Once again. Fashionably late.

Ian Happ’s Compound podcast was the only session I actually attended on Saturday. I was impressed with Yan Gomes and Tucker Barnhart, and now feel hopeful that the experience and leadership of two veteran catchers will help develop the Cubs young pitchers like Justin Steele and Hayden Wesneski. Mark Grace and Cody Bellinger talked with Happ about how Wrigley doesn’t play all that well for lefties and how you need to be a line drive hitter. Also, how the banning of the shift is a welcome rule change for lefties who were having trouble finding a place to put the ball for a hit. They talked about the importance of team chemistry and how teams have different philosophies and brands that work as a through line regardless of the players on the team. Happ does a great job as host of his show and knocked it out of the park Saturday afternoon at the first ever live taping of The Compound.

The sessions continued in the ballroom but Bleacher Jeff and I went downstairs and ended up singing with Josh and John at the Lowrey organ in the lobby. We belted out Whitney Houston and Shania Twain with Cubs fan passersby as our back round singers. Jeff even signed a few autographs as he was recognized for his ever-present presence in the LF well. We sang with our friends Lani and Nikole who I’ve known for a decade, catching games at Wrigley and in Los Angeles, where Lani lives. We sang until our voices gave out. Coming from a family of musicians that was a mix of the corny togetherness of The Brady Bunch and the blue collar chaos of Rosanne, standing around the organ singing with Josh and John was reminiscent of winter evenings with my family, singing with my sisters with my mom at the piano doing every song we knew. I think we may have stumbled on a new tradition. Cubs fan family Saturday afternoon singalong.

I hadn’t even been downstairs yet, as that’s where all the autographs are, and frankly, I don’t care about autographs and I certainly don’t like standing in lines. It’s also where the independent vendors used to be. And I say used to be, because this year, the only independent vendor was Obvious Shirts, which has partnered with the Cubs and Marquee on dozens of projects over the years. Founder Joe Johnson has become inextricably embedded in Cubs fan culture with his witty and simple T-shirts and we have become friends over the years being a part of the same Cubs fan family. I had really only come downstairs to say hi to Joe and when I found him it was towards the end of a long day of talking, selling, shaking hands, and taking selfies with the Obvious Shirt faithful. My voice was torn up from a late night and belting out Whitney Houston minutes earlier, so we shared a mutual late afternoon exhaustion and discussed a Bleacher Rules t-shirt idea we’ve been texting about. I am so proud of what Joe has accomplished. Not only does he have his finger on the pulse of what makes Cubs fans tick, because he is a Cubs fan, but he works so incredibly hard. At this point, his status within the Cubs sphere is near royalty, but he has always remained Joe who makes shirts. He’s a great guy, living the American dream as far as I can tell, and stands as an inspiration to the concept that if you have a dream and work hard, you can make that dream come true.

I headed back upstairs to the lobby where I bumped into Miguel Esparza who was with his fellow Spanish language broadcasters Noe Brito and Jorge Moreno. Over the past year, I’ve finally gotten to an intermediate Spanish level enough to where part of my practice is listening to the Cubs game in Español to improve my comprehension. Matando dos pajaros con una piedra. Killing two birds with one stone, as I clock the ballgame while learning a language. Noe and Jorge had to leave soon to go call the Blackhawks game, but we all hung out for a good hour just chatting about I don’t even know what. The Cubs I guess. Spanish. Whatever came to our minds. I don’t know, what do you talk about with friends? The topics shift, you don’t really discuss anything, you make each other laugh and you just enjoy being with each other. It’s like that with the entire Spanish language broadcast team. They are easy to talk to and easy to like and getting to know them over the past year is a testament to why learning another language is a worthwhile pursuit. It opens you up to new people and new experiences. Even though our conversation at Cubs Con was entirely in English, I never would have met them without having learned enough Spanish to listen to their broadcast. Miguel is certainly a fast rising star in his own right as his call of Christopher Morel’s first AB in the majors that resulted in a homer with a shout of “La Botooooooooooooooooo” is indelibly marked upon that memorable moment from the 2022 season. And of course his incredible Elvis Presley impersonations which I watched him perform at Harry Karaoke the night before and at the Blackhawks game the previous week

I went to dinner with Bleacher Jeff at a chicken restaurant called Nando’s which I found overpriced compared to the Jewel rotisserie chicken I eat at least weekly, and then headed back to the Sheraton for Bingo with Wayne Messmer.

I sat with the Club 400 Crew which took up at least four tables. We all shared snacks and pizza my friend Jonathan had ordered to the table. I came one away from Bingo twice, which was as close as I had ever been, but I was just as excited when my friend Tammy sitting at my table won. Her husband Darryl apologized to me because I was so close to winning but I said I didn’t care about winning and Tammy winning felt the same as me winning. We cheered and chanted “Club 400” because we all felt the same. One of us wins, we all win. When I looked around the table at the people I had met over the years at Club 400, Angela and Robert, Eddie and Brandi and their wonderful family, whose son Ryker has been a recipient of Cubs 400’s “Cubs Fans Helping Cubs Fans” charity work due to medical issues, I realized how lucky I am to be part of a group within a group. Club 400 is a community within a community and the founder Stewart McVicar has done more to bring Cubs fans together for great causes more than anybody I know.

Wayne Messmer was an amazing host as always. Except for the fact that he refuses to call my numbers, his personality is perfect. He’s funny and personable and you can feel how much he loves Cubs fans. It comes through in his voice when he’s calling the bingo game. I’ve played bingo in Vegas and it’s all very transactional and fast paced. When Wayne calls the Bingo game, it feels more like I’m at a family birthday party and my Uncle Bob is calling the numbers. He jokes and teases and generously dismisses the false bingos as we all boo the winners. He even broke the Trey Mancini news during the game. Wayne is in complete control of the convention hall turned bingo parlor as the days planned activities come to an end. It’s the perfectly fun way to wrap up the family reunion.

I was pretty wiped out after Bingo. I had talked to so many people in the past 24 hours that my head was spinning and I knew I’d be chasing the night if I hung around any longer. Harry Karaoke would have to go on without me singing background for Bleacher Jeff on Sussudio as we had the night before and the Lizzie’s crowd would have to buy their own Malört. I missed hanging with Miguel Montero at 2:30 in the morning and closing down every bar with my friends Stew and Crawly, but I did get up and write down my experiences at a very unconventional Cubs convention. Something I would not be doing had I stayed. It might have been Tuesday by the time I recovered enough to share my Cubs Con adventures with you.

What am I leaving out? Well, I talked to Bobby Dernier for a bit about the 1984 Cubs and how much that team still loves each other. I said hey to Glendon Rusch briefly; I have interviewed him in the past. I got yelled at by Clark through pantomime and a notepad that he didn’t appreciate my tweet about when his van was illegally parked by Wrigley. I shared a mic with a Harry Caray impersonator I kept accusing of being a hologram. I became Captain Cubbo’s personal photographer as so many Cubs fans wanted to get a picture with the Cubbie Caped Crusader. i hung out with Cole Wright a bit who did an amazing job reporting on the first ever televised Cubs Con. Which technically, had some of the best graphics and videos I’ve ever seen a the Convention. They seriously did a great job. So many people. So much love. So many great vibes.

Which brings me to the baseball. Cubs baseball. As far as I can tell, this team is better than last year’s team. They’ve upgraded the roster. They’ve filled a few holes with legitimate MLB caliber talent. They show signs of life with the development of the systems young pitchers. Yet, most pundits and prognosticators will predict this team at around .500, which is better than the 2022 season, but maybe not good enough for a long playoff run as the distance between the haves and the have-nots in MLB has never been greater. You can accuse me of being on the high on Cubs convention when I say this, and you’re probably right. But I can see eight more games than .500 going the Cubs’ way next year because of these positive vibes.

The new veteran players, like Hosmer, Bellinger and Swanson got to feel for the first time what it was like to have Cubs fans behind you and not against you. And the young Cubs coming up, got to feel fans’ hope for the future. What I’m saying is, this could be a case where the whole is going to be greater than the sum of its parts. They could be like the 1989 Cubs, the Boys of Zimmer, who had a couple of vets, a couple hot shot rookies and everything in between, and they somehow pulled out a magical season. Nobody had picked them to win the NL East yet they ended up the second best team in baseball that year. There were a confluence of positive things that came together that year and they won 93 games. That was the early in the career of Greg Maddux becoming THE Greg Maddux. That was when Jerome Walton and Dwight Smith, RIP, battled it out for Rookie of the Year on the same team. Jerome won but Dwight got a ring with the Braves and Greg Maddux in 1995. Nobody is going to pick the Cubs to win the World Series this year. Las Vegas has them as the 10th least likely team to win the World Series, between the Red Sox and the Marlins. But could Justin Steele become Greg Maddux? Will Matt Mervis play his way onto the Cubs and win ROY? As Cubs fans, all you can do is hope and cheer for it. For the first time since Blue Friday, when the Cubs were stripped down like a stolen car at a chop shop, I felt the sprouting of a new era for Cubs baseball. We may be at the start of something. I don’t know how long it will take to climb up the mountaintop again, but I feel the Cubs have taken their first steps up that mountain.

Allow me to conclude with the story about how I arrived at Cubs Convention around 4 p.m. Friday. I took the bus downtown and walked towards the Sheraton from Michigan Ave., where I always get turned around with the upper and lower streets. I was staring at Google map on my phone when I heard, “Danny Rockett.” I looked up and it was a guy I had met a few times at Cubs Con, and he introduced me to his friends and told me that he really enjoys watching the Son Ranto Show. We stood there chit chatting a few blocks away from the Sheraton when I once again heard “Danny Rockett.” This time, it was Ryan Dempster who I have met multiple times, interviewed and also written a parody song about the time he plunked A-Rod pitching for the Red Sox. We all sat around talking, Demp took a couple pictures with the guys and then said he needed to get to the hotel. I said “Me too” and I’m a little lost, so I’ll follow you. So Dempster and I walked to the hotel together. We talked about doing comedy and how hard it was to make people laugh sometimes. He tried out a joke on me about Brewers fans not attending college which was pretty funny and he used it later in his late night show. He told me all the guests he was going to have on. We snapped a pic together and I wished him “break a leg tonight”, shook hands and said see ya later to each other. There are so many people, players and fans that have personally touched my life.

To Ryan and all the people I mentioned in this recap of the 2023 Cubs Convention and the countless other Cubs fans who I hung out with this weekend, Thank you! Thank you for making me feel like I am part of the greatest community in the world. Thanks for congratulating me on my wedding in November and for being concerned about my cousin who recently had a stroke. You make me feel like family and the feeling is mutual. I am a Cubs fan. And it’s a wonderful thing to be.

Check out more than 130 pics from this Cubs fan weekend!