When a team comes heartbreakingly close to a title, only to come up short, it’s often fascinating to see what comes next. The 1999 Tennessee Titans came up one yard short of forcing overtime in the Super Bowl and are still waiting for a return trip. The 2011 Texas Rangers twice were one strike away from their first World Series title, but had to wait another dozen years to finally reach the mountaintop. Then there’s the 2014 Kansas City Royals, who left the tying run at third base in Game 7, but stormed back to win the franchise’s first title in 30 years the very next year.

The Sioux Falls Canaries fall in that boat now, having been three outs from their first American Association title in 17 years in Game 4 of the 2025 Miles Wolff Cup Finals. A 2-0 ninth-inning lead over the Kane County Cougars, though, turned to a 3-2 loss, then an extra-innings defeat in the decisive Game 5 followed to pull defeat from the jaws of victory.

However, unlike most professional sports, keeping your big guns for another run is much tougher in independent baseball, so the Canaries enter 2026 needing to replace many key pieces in a 2025 squad that was the best for Sioux Falls in 15 years and punctuated perhaps the most successful three-year span in franchise history.

Climbing From the Bottom

For most of their history, the Sioux Falls Canaries have been bad. Period. From their founding in 1993, the club was habitually below .500 and didn’t reach the postseason until 2001. Even that was a blip; the only winning season from 1997 to 2006.

Steve Shirley’s arrival sparked the Birds to three winning seasons and a pair of playoff berths in a four-year span from 2007-10. That stretch culminated in the AA crown in 2008 and one of the best offenses in league history in a 63-33 season and a return to the finals in 2010.

But the Birds didn’t win more than 45 games for the next dozen years after 2010. The only winning season was the fluky 2020 campaign when the Canaries stocked up on players who originally signed with other AA teams for the summer and finished 31-27 and made the AA Finals, only to lose to Milwaukee. Two more dreadful seasons followed with the return to normalcy in 2021-22.

After a franchise-worst 33-67 mark in 2023, though, the Birds turned a corner. A commitment to investing into the roster led to an impressive free agent class from manager Mike Meyer: Jordan Barth, Josh Rehwaldt, Darnell Sweeney, Hunter Clanin, Trevor Achenbach, and Akeem Bostick all were impact players signed that winter, while former Canarie Mike Hart returned.

The impact was immediate: a 52-48 record and playoff berth in 2023. They improved to 55-45 and finished second, as the Birds made the playoffs in consecutive seasons for the first time ever. That paled in comparison to 2025: 58 wins, vanquishing rival Sioux City in the first round, a five-game West Finals win over Fargo-Moorhead, then the near-miss against Kane County. As heartbreaking as the Miles Wolff Cup Finals loss was, it was still an incredible turnaround from where Sioux Falls was just three years prior.

Transition Time

As mentioned in the introduction, player retention is always a tricky task in Indy ball, and Sioux Falls is not immune. Rehwaldt, Hart, Achenbach, not to mention franchise icon Jabari Henry, are all back for ’26. On the pitching side, Thomas Dorminy returns lead the rotation, while back-end pieces Charlie Hasty and Will Levine are back in the bullpen.

However, 2025 American Association Player of the Year Calvin Estrada is off to Mexico. Fresh off a Postseason All-Star nod, Barth moved on to Banana Ball, costing Meyer his entire left side of the infield in the blink of an eye. Peter Zimmermann signed with Lake Country, further crippling the infield.

Lefty ace Tanner Brown also appears to not be playing this summer after two straight strong seasons, while second-half sensation Ryan Zimmerman retired. All-told, Dorminy is the only Canarie to make multiple starts in 2025 to return.

Meyer has a lot of holes to fill and the incoming class is on paper lacking in star power. In 2010, Sioux Falls won 63 games and lost the AA Finals, only to fall to a 42-57 mark in 2011, beginning their decade in the wilderness. A similar backslide is a fear, especially in a perennially competitive West Division.

The last three years have been just about as good as any in Canaries history, but as the winds of change blow, it remains to be seen if they bring more success to South Dakota.

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