Ranking every Chicago Cubs team since 2000

Chicago Cubs: Starting from the bottom and working our way up

22) 2012

Record 61-101

The only Cubs team in the 21st century so far to lose 100+ games. It was year one of the Theo Epstein rebuild and everyone knew this team was not going to contend. Luckily this poor record resulted in taking future Rookie of the Year and National League MVP with the second overall pick that following summer.

21) 2006

Record 66-96

Dusty Baker’s tenure as manager ended with an embarrassing season that was filled with misery and woe. Derrek Lee broke his wrist early in the season and it ended up being Mark Prior’s final year in the majors due to injuries. It did not help that fans got to hear crosstown White Sox fans reminding them of their 2005 championship all year long while the Cubs continued to falter.

20) 2000

Record 65-97

The pitching staff surrendered 904 runs, which was third-most in team history. Sammy Sosa *only hit 50 home runs and the Cubs finished dead last in the NL Central. Looking for a positive? That performance wound up resulting in the Cubs drafting Prior in 2001.

19) 2013

Record 66-96

Year two of the Epstein rebuild was rough. There was not much of an improvement record-wise from 2012 and main building block Anthony Rizzo struggled, hitting only .233/.323/.419.

18) 2011

Record 71-91

In Jim Hendry’s final season as GM, the team was lifeless and had little hope for the future. Starlin Castro was the only notable young player while the rest of the roster was a hodgepodge of washed-up veterans and AAAA players. Mike Quade did not have much of a chance to succeed. Not even trading for Matt Garza could save the team.

17) 2002

Record 67-95

Prior’s upbringing gave the team some hope and the starting rotation was actually pretty solid. Sadly the team still lost over 90 games in a pretty forgettable season.

16) 2021

Record 71-91

The end of an era. Chicago’s core of Anthony Rizzo, Kris Bryant and Javier Baez were shipped off at the deadline and a full-blown rebuild began. Fans were frustrated that not much was done in the offseason to keep this team contending, but it was clear the era was over. The starting rotation struggled mightily and the team saw multiple double-digit losing streaks. At least May was fun.

15) 2010

Record 75-87

Lou Piniella’s final season at the helm ended with a whimper. The core members of the roster were past their primes for the most part and they did not even sniff the postseason. It was an expensive roster that resulted in the first and only losing season under Piniella. Fan-favorites Derrek Lee, Ryan Theriot and Ted Lilly were shipped off for the equivalent of expired Subway coupons.