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Cubs Con 2025

It's been awhile since the team at Jacksbackstop released any content. We had a writers strike late last year as our team couldn't figure out how to navigate writing about the Cubs without jinxing them. On top of being underpaid, our team also went on their honeymoon and felt a deep sadness about the way the season ended last year. I always preach to stay on the rollercoaster through it all because without the drastic lows, the highs wouldn't feel as good. Last year tested the staff here as we went through some painful underperformances, countless blown saves, and ultimately a team that just didn't have it.


I say all that not as an excuse as to why I haven't been blogging. I could easily churn out a ChatGPT written blog that is structurally sound with Musk-like human emotions, but that's not what my readers want. My readers (and there are a lot of them) want that perfect mix of personality, passion, and data. And sometimes, when life gets in the way and the team drains the soul out of you, the blog is impacted.


I'll be posting a more proper season preview after all of the dust has settled (Bregman, bullpen depth, etc.) and the team is in AZ. But I can't properly kick off a new season without highlighting one of my favorite events of the year...the Annual Cubs Convention at The Sheraton Grand Hotel. I once again went uncredentialed because apparently the Cubs don't value alternative media outlets that bring you thoughtful pieces such as It's Time To Put Kyle Hendricks Down and Why The YMCA is the Greatest Tradition in Sports. But that didn't stop me from getting all of the best coverage to bring back to YOU, the Jacksbackstop fans.




The Panels

Outside of seeking autographs from minors (that's a reference to where they currently play baseball and not their age), the panels are where I spend most of my time. Most of the player panels are more about the personalities and less insightful but the Jed and Carter panel is always insightful. They spoke about a few things of note:

  • The Bullpen Is The Focus

    • This is obvious to anyone who watched the 2024 Chicago Cubs. They need depth in the pen and guys who can handle high leverage situations. They emphasized that this is the focus but not only because it's a need but also because it was the healthiest available market. Since the Cubs Con some big names signed elsewhere but the Cubs did manage to trade a low level pitching prospect for veteran closer Ryan Pressly. There's still a lot of guys out there that I'd like to see them pursue like Carlos Estevez, Andrew Chafin, and Jalen Beeks. None of these guys are going to WOW you like an Aroldis Chapman in 2016 but in today's MLB you need inning eaters. Most pitchers dream of getting you 5 solid innings. You need depth to get you the rest of the way

  • Scouting Department

    • Jed commented on how much of the Cubs scouting department has been fired and trimmed down. On the surface, this is an awful look. However, his perspective was that the job of a scout is to uncover unique and accurate information and in 2025 there's just less unique information. Most players, outside of maybe some international kids, have plenty of tape/breakdowns online. So that information is no longer unique and it's readily available to the organization.

  • Perspective On Park Factor

    • When the Cubs traded for Isaac Paredes last year many media pundits and fans had the same concern...this guy pulls the ball and left field at Wrigley isn't a homer friendly spot. Jed brought up an interesting point that when evaluating a guy and what kind of impact a park has on him you also have to look at the outs that he makes. So for example, Tampa has a lot of foul ball territory in left field so many of the outs that Paredes flew into would've actually been foul giving him another life. I feel like a lot of times we only look at the balls in play, specifically the homers, when it comes to park factors and don't think to check do-over balls.


Other

  • PCA has so much swag

    • Goes without saying but man is he cool. We shared a drink together at the lobby bar Saturday night* and he just has the juice. He also had one of the funnier answers to a question when talking about what it's like wearing the Cubs uniform...he said "There are so many legends that have worn this jersey before me" and proceeded to list a few Cubs only to slip Kosuke Fukudome's name in that list. What a name drop.

      *I was sitting 5 tables away from him making zero eye contact

  • Jody Davis and the Gold Card

    • We sat through a short session with Jody Davis where he basically just shot the shit for 30 mins with about 20 people. I learned about the MLB Gold Card, which Jody whipped out of his beaten up card out of his Costanza wallet and passed around, that apparently is given to a player after 8 years of MLB service and allows free admission for the cardholder and a guest into any MLB game anywhere anytime. Pretty neat.

  • The new Cubs Alts are beautiful. That baby blue, the subtle blues music references, the little cub holding a guitar...incredible

  • Auction WIN

    • I finally won an item at the live auction. Both Friday and Saturday the Cubs authentics team auctions off various game used items. Anything from a jersey to a giant light bulb out of the floodlights at Wrigley. After failing to win this item on Friday they auctioned off another on Saturday and I was able to take it home. A team used equipment trunk that lugged gear to road games from about 1970-2024. She's a beauty.





  • Pro Tip

    • If you're going to Cubs Con, don't wait in the GIANT lines for autographs. Go to the minor league tables on Saturday and catch random prospects there and get some signatures. For the kids of course...I don't do this but I'm sure some of my readers have younger kids.

  • Pro Mistake

    • Probably don't buy the mystery balls from the Cubs Charities. I like to gamble and it's for a good cause so I'll keep buying them but at $50/ball over a 2 year period we've gotten:

      • Cole Hamels (good)

      • Christopher Morel (gone)

      • Jesse Chavez (legend)

      • Felix Doubront (he had 4 starts with the Cubs)

      • Tsuyoshi Wada


Sammy Sosa

Probably the biggest takeaway from the entire weekend was the star power that Sammy Sosa has. I was 10 years old when Sammy stopped hitting nukes at Wrigley Field. Little Jack loved him and he helped me fall in love with baseball. But for 20 years he was kind of gone. All we had were videos and that shitty 30 for 30 that came out to remember what Sammy was like. I couldn't tap into my 10 year old brain and remember what it was like to see and hear Sammy.


He is an absolute entertainer. He came out on Friday night with the American flag just like he did back in 2001. The whole weekend was centered around Sammy and he knew it. Took every chance he had to run around the stage, high five everyone, hold his hand up to his ear asking for the fans to chant louder, and tell everyone how great of a baseball player he was. To some it may have come off as cocky and arrogant. But to most, it just came off as Sammy being Sammy. Mark your calendars for the Sammy Sosa and D-Lee Cubs Hall of Fame induction weekend 9/6/25.


 

Cubs Con isn't the greatest event of the year because I enjoy running around getting autographs, buying merch, and meeting players. It's the greatest event of the year because it's a weekend with my Mom talking about the thing we love the most, The Cubs. It's a weekend where there's nothing but hope and high expectations for the team as they sit at 0-0.


There is so much to be excited about with this team. They have 6 players in MLBs top 100 AND 7 players in MLB's top 100 prospects. This includes a guy in Kyle Tucker who is probably a top 10 player in baseball...finally a superstar on the Northside of Chicago.


Season preview blog to come....


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