Where Cubs Management Stands A Decade After The 2016 Championship

As the 2026 season approaches, it’s impossible for Cubs fans not to reminisce on the joy felt a decade ago when the boys in blue broke the 108-year curse to win the 2016 World Series.

It was a defining moment for the franchise and for fans worldwide. Five million people descended on Chicago for the victory parade, one of the largest gatherings in human history.

Last year, the Cubs made their first postseason since 2020, falling 3-2 to Milwaukee in the National League Division Series. It was a heartbreaking loss to an unfortunate rival, made even more painful by the Brewers’ flying of the ‘L’ flag.

In the last decade, the Cubs have made just four postseason appearances, including two National League Wild Card losses in 2018 and 2020 to the Rockies and Marlins, respectively. Their best postseason chance since breaking the curse was in 2017, when they lost to the Dodgers 4-1 in the National League Championship Series.

It’s not uncommon for teams to struggle in the seasons following a World Series win, but it’s feeling less familiar after the Dodgers’ back-to-back wins the past two years.

So what’s happened with the Cubs since 2016?

Obviously, the entire championship roster is gone, though Kyle Hendricks notably held on until 2024 before retiring with the Angels at the end of last season.

Front Office Turnover

Arguably more impactful on team performance than roster changes, especially in this case, is the amount of front-office and managerial turnover within the club.

Former Chicago Cubs President of baseball operations Theo Epstein | Jon Durr-Imagn Images

The departure of the president of baseball operations Theo Epstein in 2020 marked the longest postseason drought (five years) since the Cubs won it all. Epstein joined the franchise in 2011, after a 10-year tenure with the Boston Red Sox.

Epstein is largely credited with helping the Red Sox to their 2004 World Series victory, which ended Boston’s 86-year wait for an MLB title, and was also with the franchise for their 2007 championship. The Cubs’ 2015 loss to the Mets marked the team’s first postseason in seven years and their first NLCS appearance in 12.

Now, one man doesn’t make or break a team, but Epstein is pretty much as close as it gets.

The silver lining of Epstein’s exit? Jed Hoyer.

The Cubs’ current president worked with Epstein in Boston from 2002-2007, and both came to Chicago in 2011, along with scouting expert Jason McLeod.

McLeod declined to extend his contract and departed at the end of 2021, but was responsible for key draft selections and player development. Notably, he helped secure Albert Almora Jr. (2012), Kris Bryant (2013), Kyle Schwarber (2014), Ian Happ (2015) and Nico Hoerner (2018).

Though Hoyer is the only one remaining with the Cubs, the impact of this trio can’t be understated.

Hoyer officially took over Epstein’s role as president in 2020, and in the four seasons since McLeod left, the team has steadily improved.

Cubs Record 2020-2025 — Wins (Red), Losses (Blue) | Cubs On SI

Coaching Staff Changes

Adjustments within the coaching staff over the last decade have also affected team performance — just one of the 2016 coaches remains on the Cubs’ current roster.

Manager Joe Maddon departed the team in 2019, and former catcher David Ross took on the role from 2020 to 2023. Now, Craig Counsell is two seasons into his five-year $40 million contract. Across the three managerial transitions in five seasons, there’s been a fairly complete overhaul of the coaching staff.

Since 2016, the Cubs have had 28 different coaching roles on their staff. As it stands now, there are 17 members on the coaching staff for 2026. Of those 17, eight have been on staff since pre-Counsell (2019), and just one was on staff in 2016.

John Mallee was the head hitting coach and departed after winning the championship. He was the Phillies’ hitting coach before moving into an assistant role with the Angels, spending three years with each team. When Counsell took on the manager role in 2023, he brought Mallee back in as an assistant hitting coach, and Mallee has been with the team since.

Counsell’s various adjustments to the coaching staff displayed a lot of intention. When he joined the Cubs, there was no immediate exodus of existing coaches. Counsell kept 12 of the 18 coaches from the previous season under Ross, and only four have left the club.

It’s hard to believe the 2016 season was 10 years ago.

The Cubs have won and lost a lot over the last decade, and a lot has changed. It’s the beauty of baseball. Some losses were tougher than others, but things seem to be looking up.

The addition of Counsell and last season's success have shown fans one thing: hope is still alive in the Friendly Confines.

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