Back in 2018, I launched a Dynasty League with many of the Chicago Bears content creators that you all know and love, and many of them are regular contributors at Windy City Gridiron and 2nd City Gridiron.
It’s been a fun league and a few days ago, our guy Jeff Berckes said to me, why don’t you write about the league on Windy City Gridiron, I thought about it and wondered if fans would want to hear abou it, and our big boss man, Lester Wiltfong, thought it might be a fun exercise to do, especially
in the offseason (depending on how much you guys like this series, we can continue it periodically during the season if you guys are hungry for updates).
I have grown to love dynasty fantasy football. I have found redraft leagues boring, even offense-only leagues where you keep a couple of players aren’t enough for me. I love dynasty leagues, especially ones that feature individual defensive players. I am in three leagues, this one included.
We will analyze the draft, the rosters, and the best ways each of these managers should work moving forward. I think it will also be an opportunity for other dynasty players to use this league as a resource to get opinions on how they value their players and get fresh opinions.
There aren’t many resources on the Internet that deal with dynasty leagues, and the ones that do usually only rank offensive players. If your league has offensive and defensive players, there are practically zero resources that show you how to build on both sides of the ball and what you should value in the draft. Should you draft Sonny Styles or KC Concepcion? These answers are not found on the Internet, so I am hoping to provide some insight as to how some smart football people look at leagues that have that juxtaposition.
This first article is to introduce you to the league, and then we will discuss the draft and analyze how each team did.
The owners, as we enter year nine of the league:
Bill Zimmerman: I actually started the league back in 2018. I started my first dynasty league in 2015, joined another in 2017, and started this one in 2018. I’ve won the league championship 3 times and appeared in the championship game another three. I decided to start rebuilding my roster a couple of years ago, and we are hoping the team is about ready to start competing again.
Lester Wiltfong: The two dynasties in the league overlapped a little with Lester and me. Consider myself the Shaq/Kobe Lakers and Lester the Duncan/Parker Spurs. One of the original members of the league, Lester, always competes. While I decided to do a full rebuild after my team aged, Lester has stayed competitive and reached the semifinals this past season. Lester has appeared in three championship games and won them all.
Mason West: The host of the Bear Bones podcast, Mason joined the league a few years ago and has a similar philosophy to that of the LA Rams: F*ck them picks. Mason consistently trades away his draft picks for strong veteran players and rebuilds a team in a few years, and landed himself the championship in 2025.
[Redacted]: [Redacted] also wasn’t an original participant but joined a few years into the league and has put together a strong roster that always competes for the championship. Why are they [redacted]? Maybe they just don’t want their name publicly, or maybe they are someone in football who can’t be in a public league, but we will talk about them, nevertheless. [Redacted] has one championship game appearance but no championship trophies.
Brandon Robinson: Brandon has made many appearances on Chicago Bears podcasts over the years and has contributed to various websites. He’s another strong dynasty player who has his team in the playoffs most seasons. He made his first title game appearance in 2025, but lost the game to Mason West.
Dan Meehan: Danny is one of the original members of the league (one of six of us remaining). Danny is, of course, the co-host of the Bear Bones podcast and has appeared on other podcasts on the 2nd City Gridiron podcast channel. Danny’s team struggles with the dangerous word: purgatory. He’s almost always in the playoffs as one of the lower seeds and has yet to appear in a championship game; his team also never finishes near the bottom of the league.
Kevin Hand: Kev has been a part of the Windy City Gridiron family for many years, including years before I joined Lester’s band of merry men. Kev had a strong team early in the league’s history, but has had his team fall into tough times and is working through a rebuild. Kev has appeared in one championship game, but does not have a trophy to his name. Kev is one of the original six.
Tyler Volz: You have a better chance to see Tyler as the ring announcer in a professional wrestling league than you do on a Bears podcast, but he’s been a part of the Bears Twitter community for many years. Tyler’s teams struggled early in the league’s history, but he has steadily built a contender and has been to the championship game 2 of the last three years, winning one title. Tyler is also part of the original six.
Will Ingalls: Will is the sixth member of the original six. Will had a good team early, built it to a great team, but couldn’t get over the hump in the playoffs. Will reached one title game, but lost and could never get over the championship game hump. He entered a rebuild a year ago.
Adam Hess: Of all the non-original members, Adam is one of the longest tenured members of the league. His team has been near the bottom of the standings the last few years, and Adam is working through a rebuild to try to bring his team to heights he has yet to reach.
Jacob Infante: We had some major turnover this year, but the league is stronger for it. Jacob is one of 4 new league members this year; we had never had more than one new league owner previously. Jacob takes over a team that has a serious rebuild in front of it. If anyone can do it, it’s the NFL Draft guru.
Jeff Berckes: JB takes over a roster that is entering year five of its rebuild and is still consistently picking in the top three. It’s not JB’s fault; it’s his first year managing the roster. Will JB get this one out of the cellar? He has a few nice foundational pieces to build upon.
Quintin Krysko: Q joins the league this year and is, of course, part of our friends at Bears On Tap. Q has taken over a team that never had much direction and needs someone committed to building through the draft, something Q knows quite well.
Ron Luce: Ron is the fourth new member this year and has only been a part of the league for two months, and you already know he’s a great addition. Ron loves to wheel and deal, and I think he has made more trades than anyone else since he’s joined the league. Ron also comes from Bears on Tap and has a team similar to Qs that needs some TLC to get back on track.
Here’s a look at the championship game results in the history of the league:
2025: West over Robinson
2024: Volz over [Redacted]
2023: Wiltfong over Volz
2022: Zimmerman over Ingalls
2021: Wiltfong over Zimmerman
2020: Wiltfong over Zimmerman
2019: Zimmerman over Hand
2018: Zimmerman over Read (Ross Read, no longer in league)
We will continue with more articles dedicated to this dynasty league and dynasty content throughout the offseason. Please comment below if there is any specific content you are looking for, and we would be happy to try to oblige.
