Ranking every Chicago Cubs team since 2000

It is easy to point out and rank the very best seasons in Chicago Cubs history, but ranking the rest is hardly a cut and dry discussion. When the 21st century began, the Cubs had a grand total of three postseason appearances (1984, 1989, 1998) since 1945 and zero series wins in those showings. During that same 54-year span, they had only four years in which they won 90 or more games.

Since 2000, however, the Cubs have been to the playoffs eight times, won seven playoff rounds and had five 90+ win seasons. Oh, and a pennant and World Series win. Certainly did not see that from 1946-1999.

The last 22 years as a whole sure brought a lot more joy to Cubs fans than the previous 54, but there has still been plenty of pain and suffering over the past two decades. Chicago has had seven 90+ loss seasons since the new millennium hit. We have seen some of the very best and very worst of Cubs baseball since 2000.

Just for fun, let’s take a look at each of those squads and put together a rankings list. There will be three tiers: the bottom of the barrel, middle of the pack and the best of the best.

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.

Chicago Cubs: Even so-so clubs were better than most from previous decades

14) 2014

Record 73-89

The first half of the season was awful, but the second half saw better baseball and a look toward the future. Rizzo made his first All-Star game, Baez and Jorge Soler came up from the minors and Jake Arrieta began his dominant run as he pitched to a 2.53 ERA, 2.26 FIP and 0.99 WHIP in 25 starts.

13) 2005

Record 79-83

Derrek Lee’s MVP-caliber season was all Cubs fans really had. Him hitting 46 home runs with a .335/.418/.662 slash and 50 doubles was awesome. Everything else was just “blah”. Not terrible but not great.

12) 2009

Record 83-78

After back-to-back postseason-bound seasons in ’07 and ’08, the 2009 season was the very definition of mediocre. Expectations were very high, but they finished 7 1/2 games behind the Cardinals. The pitching staff regressed and the offense was not nearly as productive as the year before. It also did not help that Aramis Ramirez missed significant time due to a shoulder injury.

11) 2019

Record 84-78

Joe Maddon’s final season in Chicago was the only campaign in which the Cubs did not make the postseason during his tenure. Despite quality performances from the core players, the bullpen blew an insane amount of games and the defense was uncharacteristically bad. They looked out of focus and not even Nick Castellanos was enough to propel them back to October.

10) 2001

Record 88-74

Don Baylor’s squad surprised many with a competitive season. They did not make the postseason but they were in the thick of it right until the end. It was only the third season which the Cubs finished with over 85 wins since 1985. Sammy Sosa hit 64 home runs and starter Jon Lieber made the NL All Star team.

9) 2004

Record 89-73

Arguably the most disappointing ending to a regular season since 1969. The team was all-in on going to the World Series with a rotation of Mark Prior, Kerry Wood, Greg Maddux, Carlos Zambrano and Matt Clement. It ended with a collapse in the final week of the season which saw Sosa walk out on the final day and Steve Stone resigning from the TV broadcast booth after tension between him and organization piled up. It was ugly and frustrating despite winning 89 games.