The 2016 Cubs legacy: eight years on from the curse-breaking season
Eight Septembers ago, a city starved for a century finally exhaled. When Anthony Rizzo fielded the final out at Progressive Field and the Cubs became World Series champions, the longest drought in North American professional sports ended in a single, unforgettable swing of Billy Hamilton's bat and the tears of a generation. The team that delivered that night, however, has since scattered across the league, the coaching ranks, and the broadcast booth, leaving behind only echoes and a nameplate on a trophy case.
Looking back now, the 2016 roster reads like a who's who of baseball's recent decade. Most of those names have aged in unusual ways, transforming from heroes into veterans, mentors, and in some cases, front-office executives. What follows is a snapshot of where the championship Cubs landed and what the franchise itself has become in the years since that rainy November evening.
The position players who became building blocks
Kris Bryant walked into Cleveland as the reigning MVP and walked out as a world champion. His post-2016 trajectory took him through Colorado and San Francisco before he settled into retirement. Anthony Rizzo has carved out a second life with the Yankees, becoming a veteran leader in the Bronx after leaving Chicago as a free agent. Javier Baez returned to Detroit and then bounced toward the Mets, bringing his trademark flair and inconsistent strike zone with him. Kyle Schwarber reinvented himself with the Phillies, transforming from a defensive liability into a designated hitter capable of forty home runs in a season.
Addison Russell's career stalled after off-field controversies, while Willson Contreras has been one of the few constants, anchoring a position that has seen more turnover than most Cubs fans would have predicted. Jason Heyward, whose defence saved more runs than his bat produced during those magical playoffs, has largely faded from the league. The collective trajectory of that group tells a familiar championship story, namely that contention windows close faster than cities expect.
The pitching staff scattered across baseball
Jake Arrieta brought his postseason legend into subsequent seasons but never recaptured that 2015 to 2016 peak, drifting through Philadelphia, Baltimore, and finally the Cubs' bullpen for a brief homecoming. Jon Lester called it a career in 2022 after finishing out with St. Louis, his left arm wearing down just as the next generation of Cubs arms was rising. John Lackey retired around the same time, content with three rings across three franchises.
The bullpen names from that October carry more weight in the conversation now. Carl Edwards Jr. spent years as a reliable setup man before injuries cut into his production. Pedro Strop became a cult hero at Wrigley, his entrance music a soundtrack for an entire era of late-inning drama. Closer Aroldis Chapman, famously acquired midseason that year, has bounced from the Bronx to the West Coast and back. Mike Montgomery, who recorded the final out of the World Series, has since moved into coaching, which is the natural destination for any pitcher who spent years operating under baseball's most scrutinised spotlight.
The front office and the patient rebuild
Theo Epstein stepped away after the 2021 season, exhausted by two rebuilds in two cities. His departure marked the end of an era that began when he inherited a ninety-loss club and reshaped it into champions. Jed Hoyer took over the top job and soon presided over the painful teardown that traded nearly every remaining face from the 2016 roster. Whatever the rebuild looked like in real time, there are now signs that the patient approach is starting to bear fruit across the diamond.
The roster Epstein left behind is largely gone, replaced by prospects who have graduated into everyday players. The Cubs fielded one of the strongest young rotations in the National League during 2025, anchored by homegrown arms and supplemented by measured free-agent signings. Detailed coverage of the rebuild outlines how the front office has approached this second window compared with the rushed attempts of the late 2010s.
Australian fans and the morning game tradition
For Australians, the 2016 Cubs became a curious cultural export. With Chicago sitting around sixteen hours behind eastern Australian time during daylight savings, World Series games aired in the early hours of the morning. Most Cubs fans in Melbourne and Brisbane caught the historic clincher on replay, watching it in the late arvo before logging into work. MLB has since expanded its reach in Australia through streaming packages and the occasional international series.
The Australian Baseball League continues to develop talent from places like Sydney and Perth, with the Brisbane Bandits and Adelaide Giants regularly producing players who reach affiliated ball. A handful of Australians have filtered through MLB systems since 2016, including closer Liam Hendriks, whose career has taken him through several American League cities. The MLB's brief 2014 season-opening series at Sydney Cricket Ground opened a permanent door, and Australian audiences have never fully closed it.
Anyone with a take on the championship generation can find a growing community of Aussie fans on the site ready to debate and document the passion for the franchise from a Southern Hemisphere perspective.
Comparing the 2016 team to today's Cubs
The roster construction looks almost nothing like the championship club. That team was built around three stars under twenty-six and a free-agent splash for Heyward. Today's club leans more heavily on pitching and positional versatility, with several players capable of playing two or three spots in any given week. Manager Craig Counsell, who joined the Cubs after winning the National League pennant with the Brewers, brings a calmer bench presence than Joe Maddon ever offered.
The table below offers a side-by-side look at how the franchise has changed:
| Category | 2016 Cubs | 2026 Cubs |
|---|---|---|
| Manager | Joe Maddon | Craig Counsell |
| President of Baseball Operations | Theo Epstein | Jed Hoyer |
| Top Position Player | Kris Bryant | Pete Crow-Armstrong |
| Top Pitching Acquisition | Aroldis Chapman | Free-agent arm |
| Ballpark Attendance Rank | 4th in MLB | 6th in MLB |
| Estimated Payroll Rank | 6th in MLB | 11th in MLB |
| Last Postseason Appearance | World Series champions | 2025 NL wild card |
The contrast illustrates how dramatically the roster rebuild has reshaped both the on-field product and the organisation's broader posture.
The Maddon method and its modern echoes
Joe Maddon never stayed put anywhere. After leaving the Cubs in 2019, he resurfaced with the Angels, where his trademark themed road trips and casual leadership style made less of an impact than they had in earlier years. Maddon eventually stepped away from managing and now writes, speaks, and occasionally consults. His fingerprints remain visible across the modern game, particularly in the way teams approach rest days and the use of relaxed clubhouse policies.
Counsell represents a different school, slower in tempo, quieter in personality, deeply analytical in approach. The transition between those two voices mirrors the broader shift in how organisations value dugout temperament. Around the league, the manager who can communicate with the front office tends to last longer than the one who simply manages, and Maddon eventually paid the price for wearing out his welcome in clubhouses that wanted more structure.
What lies ahead for the North Siders
The window appears to be opening again. With several young arms under team control and a handful of position players approaching their arbitration years, the Cubs look ready to spend in a way they have not since 2017. The question facing Hoyer and his staff is whether to reload aggressively with free agents or to continue developing from within.
Australian-based followers might keep an eye on early-morning west coast broadcasts that line up nicely with a 4am alarm for those who insist on live viewing. The clocks change in Sydney, Melbourne, and Brisbane just as the regular season begins, making April and May an ideal window for fans across the Tasman to catch marquee matchups in real time without sacrificing too much sleep.
Practical notes for following the Cubs from down under
For fans tuning in from Australia, a few practical considerations help make the season more watchable:
- Pick a streaming service that offers condensed-game replays for late-night fixtures, particularly during west coast Cubs games that wrap around 7am AEDT.
- Sign up for MLB.TV if you want full access to every pitch, but be ready for blackout restrictions on local broadcasts of opposing clubs during their home stands.
- Join an Australian baseball or MLB fan community online, where timezone-tolerant mates often swap real-time updates during prime-time US games.
- Plan around international series when the Cubs travel to Asia or close to your timezone, as the time difference occasionally flips in your favour.
- Try to catch a spring training broadcast if you ever find yourself in Arizona or Florida during February, when scheduling lines up nicely with the close of the Australian cricket season and the early-morning sessions feel almost natural.