The Future of CCW: 16 Years of Champions, Guaranteed (Probably)

The history books of Circle City Wiffle tell a story of shifting dynasties, legendary performances, and the occasional defunct franchise (RIP Kings of Diamonds, Skeeters, and Noodlers). From Brendan Dudas’ reign of terror in the mid-2010s to Will Smithey’s Moonshots dynasty and Myc Witty’s emergence with the Hounds, CCW’s championship lineage has seen its fair share of dominance.

But why stop at looking back when we can look forward?

With the 2025 season fast approaching, we could have played it safe—offering basic predictions like everyone else. Instead, we turned to the most powerful tool known to man: Artificial Intelligence (which has never been wrong, ever).

We’re not just calling the 2025 champion. We’re mapping out the next 16 years of CCW titles—every dynasty rise, every power shift, and every expansion team that will shake the league to its core.

Bookmark this. Screenshot it. Laugh now, but when a “Caleb Vance” or “Brady Castner” enters CCW in 2035, just remember: we told you first.
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Let’s get into it. The CCW dynasty map awaits...

2025 Champion: Hounds
Team MVP: Dylan Jones
The loss of Myc Witty leaves questions about whether the Hounds can stay on top, but the defending champs refuse to go quietly. With Jake Sprinkle and Austin Alles stepping into larger roles, they maintain elite depth on the mound. Jones becomes the offensive centerpiece, carrying the lineup while Sprinkle and Coby Taylor anchor the pitching staff. They outlast the Short Shorts in a grueling championship series, solidifying themselves as a CCW powerhouse with their second title in three years.

2026 Champion: Short Shorts
Team MVP: Myc Witty
After over a decade of falling short, the Short Shorts finally reclaim the CCW throne. Witty proves his move from the Hounds was the right call, putting together a legendary season on the mound and at the plate. Devon Hensley becomes a crucial contributor, providing the offensive consistency the Shorts lacked in past playoff runs. In the end, the Shorts snap a 11-year title drought, capturing their first championship since 2015.

2027 Champion: Stampede
Team MVP: Holden Palmer
One of the longest-tenured teams without a championship finally breaks through. After years of playoff heartbreak, the Stampede build a dominant core, led by the Palmer brothers and the emergence of Tristan Dudas as an offensive force. Their defensive versatility and relentless pitching staff make them a nightmare matchup, allowing them to outlast the defending champion Short Shorts in a tight championship series.

2028 Champion: Yakkers
Team MVP: Alec Buchman
One of CCW’s oldest teams finally puts it all together, claiming their first championship. The Yakkers build a deep, balanced roster, relying on elite pitching and clutch hitting. Alec Buchman emerges as one of the best arms in CCW, and the team’s small-ball approach helps them grind out low-scoring wins. The championship marks the beginning of a new contender in the CCW hierarchy.

2029 Champion: Moonshots
Team MVP: Ian Garavalia
The Moonshots reclaim their place atop CCW, winning their first title since 2022. Garavalia evolves into a true two-way force, dominating both at the plate and on the mound. Alongside Jaxon Ridgeway, whose speed and defense give the team an extra edge, the Moonshots overwhelm their opponents with a mix of power, athleticism, and elite pitching depth. The championship cements the Moonshots as one of CCW’s most successful franchises.

2030 Champion: Hounds
Team MVP: Austin Alles
With many of their original championship core aging out, the Hounds reload and return to the top. Austin Alles steps into the leadership role, carrying the offense with his balanced power-speed game. Jake Sprinkle and Coby Taylor provide key depth, and the Hounds’ pitching staff remains elite, allowing them to grind through another deep postseason run.

2031 Champion: Short Shorts
Team MVP: Mitch Unversaw
The Short Shorts refuse to fade, proving their 2026 title was no fluke. After losing some key veterans, the Shorts reload with a new wave of talent. Mitch Unversaw becomes the franchise’s next star, using his speed and contact hitting to lead one of the league’s most potent lineups. The Shorts ride an explosive offense to their third championship.

2032 Champion: Expansion Team - Cyclones
Team MVP: Colton Beasley
Expansion shakes up the league, and the Cyclones waste no time making history. Behind Colton Beasley, an electric two-way player, they storm through the league in their debut season, delivering a shocking championship. Expansion teams have had success before in CCW history, but none have done it this fast.

2033 Champion: Expansion Team - Mammoths
Team MVP: Landon Cline
Another expansion team crashes the CCW elite, this time using a power-first approach. The Mammoths build their roster around dominant hitting and strong pitching, with slugger Landon Cline leading the charge. Cline puts on a postseason clinic, crushing game-winning homers while the Mammoths ride a deep pitching staff to the title.

2034 Champion: Moonshots
Team MVP: Jaxon Ridgeway
Now in his prime, Ridgeway dominates, leading the Moonshots back to the top. Their elite pitching staff and well-rounded lineup make them nearly unstoppable, and their third championship in 13 seasons cements them as a CCW dynasty.

2035 Champion: 8 Balls
Team MVP: Reid Werner (Final Season)
In a storybook ending, CCW legend Reid Werner closes out his career with one last championship. The 8 Balls, one of CCW’s most respected franchises, blend veteran leadership with young talent, including rookie Caleb Vance, who steps up in the biggest moments. Werner rides off into the sunset as one of CCW’s greatest of all time.

2036 Champion: Stampede
Team MVP: Brady Castner
The Stampede’s second wave of stars takes over, and Brady Castner establishes himself as the best player in CCW. His elite two-way play drives the team, while the Palmer brothers provide the veteran leadership needed to win tough playoff matchups. The Stampede prove their 2027 title wasn’t a fluke, solidifying their place among CCW’s great franchises.

2037 Champion: Expansion Team - Clippers
Team MVP: Miles Davenport
Yet another expansion team breaks through, and the Clippers make a historic run. Miles Davenport, a defensive wizard and dynamic leadoff hitter, leads a young, exciting team to a championship in just their second season. The Clippers immediately become one of CCW’s must-watch franchises.

2038 Champion: Short Shorts
Team MVP: Cade Sullivan
The Short Shorts return to dominance, winning their fourth title. Cade Sullivan steps up as the new franchise cornerstone, delivering clutch performances while playing elite defense. Their long history of perseverance pays off, proving they are one of CCW’s all-time best teams.

2039 Champion: Hounds
Team MVP: Dawson Redman
The Hounds rise again, proving that championship DNA doesn’t fade. Dawson Redman, an underrated but deadly clutch player, delivers game-changing moments, leading the Hounds to another championship.

2040 Champion: Moonshots
Team MVP: Tate Willoughby
Tate Willoughby puts the league on notice, dominating on the mound and carrying the Moonshots to yet another title. This win solidifies the Moonshots as a CCW dynasty, matching the Hounds and Short Shorts as four-time champions.

The Future is Written—But 2025 is Now
Sixteen years of triumph, heartbreak, and dynastic dominance lie ahead, their champions etched in the annals of CCW history before a single pitch of 2025 has even been thrown. Legends will rise, expansion will shake the league to its core, and franchises will forge their legacies in the fire of competition.

Yet, for all the prophecy and foresight, one truth remains: CCW is unpredictable.

No AI, no algorithm, no force of nature can account for the grit of an underdog, the resurgence of a forgotten star, or the madness of October wiffleball. Will the Hounds reclaim their throne? Can the Short Shorts finally end their title drought? Or will a new contender emerge from the shadows?

All the speculation ends here. The path to greatness begins now.

​Welcome to the 2025 CCW season.