As the calendar flips to another cold December in Chicago, the North Side faithful find themselves reflecting on what it means to call a baseball season a success. With the 2025 campaign now in the rearview mirror, fans and analysts alike are deep in debate: Did the Cubs meet expectations, or is the bar simply set too high for a franchise with such a storied—and sometimes tortured—history?
These musings come amid a flurry of nostalgia, as the city prepares to welcome back 17 members of the iconic 2016 World Series champion Cubs at the upcoming Cubs Convention in January 2026. Among them is Miguel Montero, whose journey from postseason hero to unlikely pitcher and, eventually, to a beloved alum, perfectly encapsulates the unpredictable rollercoaster that is Cubs baseball.
Let’s rewind to one of the most peculiar yet memorable moments in recent Cubs lore. Before Montero etched his name into Chicago baseball history with his clutch grand slam in the 2016 NLCS against the Dodgers and his pivotal hit in the 10th inning of Game 7 of the World Series, he found himself on the mound—a position he never imagined he’d occupy in a Cubs uniform.
It was July 3, 2016, and the Cubs, on their way to a 103-win season, were mired in an inexplicable 5-15 slump. The team looked nothing like the juggernaut that would eventually end a 108-year championship drought. On that fateful Sunday at Citi Field, the Cubs were already down 13-1 to the New York Mets. Jon Lester, usually the rock of the rotation, was shelled for eight runs in less than two innings—his worst outing in 171 starts with the Cubs. The Mets’ bats, led by Curtis Granderson, Wilmer Flores, and future Cub Rene Rivera, battered Lester with three home runs. Relief pitchers Spencer Patton and Joel Peralta didn’t fare much better, each surrendering another home run. For Peralta, it was one of only five appearances in a Cubs uniform before he was designated for assignment just days later.
With the game spiraling out of control, manager Joe Maddon made the kind of move that only happens when all hope is lost: he called on Miguel Montero—a catcher by trade—to take the mound in the bottom of the seventh. Montero, facing a runner on first and two outs, managed to induce a ground ball to escape the inning unscathed. But the eighth inning was less forgiving. Montero surrendered four hits and allowed a run, but the damage had long been done. The Cubs limped out of Citi Field with a 14-3 loss, capping a four-game sweep at the hands of the Mets and a combined deficit of 18-8 over the series.
As if one pitching appearance wasn’t enough, Montero returned to the mound in 2017, this time at the Friendly Confines of Wrigley Field. The Cubs were trailing the New York Yankees 11-6 in the late innings. After pinch-hitting for Rob Zastryzny in the bottom of the eighth—and driving in two runs with a single, no less—Montero stayed in to pitch the top of the ninth. He issued two walks and threw a wild pitch, but managed to keep the Yankees off the board. The Cubs, however, went quietly in the bottom half, sealing an 11-6 defeat.
These cameo pitching appearances might seem like footnotes in the grand scheme of Cubs history, but they’re emblematic of the unpredictable, sometimes chaotic, always entertaining nature of baseball on the North Side. In fact, under current MLB rules, teams can only use position players as pitchers if trailing by at least eight runs. Montero’s 2017 outing, with the Cubs down by only five, would be prohibited today.
Montero’s time in Chicago wasn’t without drama. His departure from the team later in 2017 was, as some put it, “somewhat acrimonious.” Yet, time heals most wounds in sports, and Montero has since been welcomed back to Wrigley Field as an honored guest. His return for the 2026 Cubs Convention, alongside 16 other members of that championship squad, is sure to stir up memories—both triumphant and bittersweet—for fans and players alike.
So, what does all this say about the 2025 season? The debate rages on. Was it a success? The answer depends on your perspective. For some, success is measured strictly by wins, losses, and postseason hardware. For others, it’s about the moments—the grand slams, the unlikely heroes, the camaraderie, and the stories that will be told for generations. According to the North Side Baseball Caretaker Fund, the heart of the Cubs community beats strongest when fans rally together, not just for championships, but for the love of the game and the memories it creates.
“You all care about this site. The next step is caring for it,” reads a message from the North Side Baseball Caretaker Fund, encouraging supporters to help maintain the premier Cubs community online. It’s a sentiment that mirrors the spirit of Cubs fandom—enduring, passionate, and ever-hopeful.
As the Cubs prepare to celebrate their past while looking toward the future, the stories of players like Montero remind us that baseball is as much about resilience and redemption as it is about statistics and standings. The 2025 season may not have ended with a parade down Michigan Avenue, but it added another layer to the rich tapestry of Cubs history. With legends returning to the fold and a new generation of fans and players ready to write the next chapter, the question of what defines success remains as lively—and as debatable—as ever.
With the Cubs Convention on the horizon and the echoes of seasons past still ringing through Wrigleyville, one thing’s for sure: the North Side’s love affair with baseball is far from over. Whether the 2025 season is remembered for its highs, its lows, or its unforgettable characters, it’s clear that the Cubs’ legacy is built on more than just wins and losses. It’s built on moments—some magical, some maddening, but all uniquely Cubs.
