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: 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.

Chicago Cubs: There were several great teams, but one stands alone

8) 2020

Record 34-26

It was difficult to rank this one, since the 2020 COVID-shortened season was only 60 games. They won the division and were swept in the Wild Card round. Hard to compare this season to others, but they did win a division title despite an anemic offense.

7) 2007

Record 85-77

From worst to first, the 2007 team finished with a mediocre-ish record but they were able to clinch an NL Central title. Piniella’s squad started off very poor but they caught fire in the final months to clinch a postseason berth. Alfonso Soriano was signed to a big deal and Mark DeRosa fit in nicely with Lee and Ramirez. Sadly the Cubs were swept in the NLDS.

6) 2003

Record 88-74

Mark Prior and Kerry Wood led a surprising campaign to a division title and one win away from the World Series. Everything fell into place in the second half as they edged out the Astros in the NL Central. Their NLDS win was the Cubs’ first postseason series win since the 1908 World Series and the Cubs got as close as five outs from a pennant. Until 2016, they were the closest Cubs team to pennant since 1945. Despite the soul-crushing ending, it was a great year under Dusty Baker.

5) 2018

Record 95-68

It was heartbreaking seeing the offense break in the final weeks and the Brewers overtake the Cubs in 163 games. The Wild Card loss at home felt inevitable. That said, they still won 95 games as the starting pitching performed pretty well. Only 12 other teams in Cubs history finished with more wins. There were some epic wins, including two walk-off grand slams from Jason Heyward and David Bote, it just was not quite enough to win the division in the end.

4) 2017

Record 92-70

A World Series hangover in the first half of the season did not ruin the defending champ’s season in the end. A second-half surge got the Cubs another division title and they returned to the NLCS for the third straight year. Even if it felt nowhere near as good as 2016, it was still a memorable campaign in which they were three wins away from returning to the World Series. The 2017 season also marked the first time in franchise history which the Cubs made the postseason in three consecutive years.

3) 2015

Record 97-65

Joe Maddon’s first season saw the young Cubs shock the world. Kris Bryant came up and won NL Rookie of the Year, Jon Lester put up a very good first season as a Cub and Jake Arrieta put on a historic Cy Young-winning performance. While competitive in the first half, they went on a surge in the second half. The upcoming Cubs beat the Pirates in the Wild Card game and took down the rival Cardinals in the NLDS. It was obvious this team was special when Kyle Schwarber was hitting mammoth home runs in the playoffs.

2) 2008

Record 97-64

It really looked like this team was going to be “the one”. The offense of Lee, Ramirez, Soriano, DeRosa, Ryan Theriot, Geovanny Soto and Kosuke Fukudome scored 855 runs. The pitching staff dominated with a 3.87 ERA. They had a +184 run differential. The Cubs had eight representatives in the All-Star game and they finished with the most wins in a season since 1945. It was shocking to see this team get swept in such awful fashion in the NLDS. Despite the lackluster showing in October, this was the most dominant team we have seen in the past 22 years outside of our highest-ranked squad.

1) 2016

Record 103-58-1

100+ wins, 252 run differential, 3.15 team ERA, .772 team OPS, NL Central title by 17 1/2 games, NL Pennant and the franchise’s first World Series championship in 108 years. What else has to be said?

Cubs fans need to hope that the next 22 years are even better than the last 22 collectively. There were a lot of bad seasons but the highs were great. Hard to believe we are already two decades into the 21st century.