Starters
1. Mark Prior 2003 18-6 2.43 ERA 3 CG 1 SHO 57 ER 245 K 1.103 WHIP 178 ERA+
What Prior did that season still ranks as one of the greatest pitcher seasons I have ever seen. Too bad for Prior he picked Eric Gagne's top steroid season to do it. Jason Schmidt was awesome that year too. Still Prior finished third in the Cy Young voting and made so many of us think he would do that every year until he was 40. As is the theme with many players of this decade- Prior never really was healthy again and never repeated his 2003 magic. Still we can look back at that season at remember how dominating he was.
2. Carlos Zambrano 2004 16-8 2.75 ERA 1 CG 1 SHO 64 ER 188 K 1.216 WHIP 160 ERA+
This won't be Z's only appearance on this list, but it is his best overall season as a Cub. He finished fifth in Cy Young voting, and I knew then the Cubs had themselves a damn good pitcher. Had you said then that of Kerry Wood, Prior, and Z that Z would ultimately have the best career I would have thought you were crazy, but as we all know Z has turned himself into one of the stars of the game while Prior is still hurt and Kerry is closing games in Cleveland. Z is also a great example of what happens when a team develops its own starting pitcher, something the Cubs haven't done since.
3. Ryan Dempster 2008 17-6 2.96 ERA 1 CG 68 ER 187 K 1.210 WHIP 151 ERA+
Nobody defined the 2008 Cubs better than Dempster. He wasn't even going to make the team out of spring training, only to become one of the best pitchers in baseball during the season. He was able to combine great preseason conditioning with a nifty glove wave and baffled hitters all season. Then came his playoff meltdown (something I will never ever forgive him for) and it all went away. Still Dempster was great in the regular season and good for him getting a long term deal that rewarded him for such a great comeback from arm problems.
4. Rich Harden 2008 5-1 1.77 ERA 14 ER 89 K .0972 WHIP 252 ERA+
This begins the hard decisions. Basically Big Z could finish out this list with his 2003 and 2006 seasons. Trust me I will debate these final two selections for some time, and I encourage all of you to do so in the comment section. On to Rich- Harden was the big trade in July 2008 for Jim Hendry. He came with much fanfare and was hailed by many as the missing ace for the Cubs who would put the rotation over the top. Of course that didn't happen, but Harden was still great in the regular season. Sure he can't throw more than six innings, but those were always fun innings to watch. Lots of strikeouts and awesome change-ups. Harden brought Prior 2003 like fun to the mound for a few months.
5. Jon Lieber 2001 20-6 3.80 ERA 5 CG 1 SHO 98 ER 1.149 WHIP 109 ERA+
I had to resist putting Z on the list again, but Greg pointed out that the only 20 win season of the decade deserves mention. I agree, plus Big Z has plenty of love coming in this series. Lieber was the only 20 win pitcher of the month, and was quite the horse with five complete games. He finished fourth in Cy Young voting and him being on the mound was one of the fun things that year. Him and Kerry Wood formed quite the duo that year, and Lieber certainly carved himself a place in Cub trivia for a very long time.
Honorable Mention: Z 2003 (13-11 3.11) 2005 (14-6 3.26) 2006 (16-7 3.41) 2007 (18-13 3.95)
Bullpen
Keep in mind I am more than willing to fill this list with seven closer seasons, but there have been some good setup men. There will be a few random names on here, but that is the beauty of a bullpen. Random guys have random good seasons. This will illustrate that point.
Todd Van Poppel 2001 4-1 2.52 ERA 75 IP 90K 1.347 WHIP 164 ERA+
It doesn't get more random than this, and I honestly can't tell you one thing about Van Poppel or his vaunted 2000 season. Still ERA+ is very indicative of good pitching, and I weighed it very highly in my rankings so Van Poppel gets a mention. Van Poppel did have a long career starting in 1991 and ending in 2004. Six teams, and his only two real good years came with the Cubs. He also got two hits at the plate in 2001 completing his dream season.
Joe Borowski 2003 2-2 2.63 ERA 68.1 IP 33 SV 1.054 WHIP 164 ERA+
I can speak about Borowski's 2003 season with a bit more knowledge. He was the closer for a team that made a great playoff run, and he did his job well. 33 saves is nothing special, but he was able to do that job and actually did it without causing too many heart attacks at Wrigley. Borowski struggled with injuries for a while after 2003, but nobody can diminish his role on the key team of the decade.
Kent Mercker 2004 3-1 2.55 ERA 53 IP 1.245 WHIP 173 ERA+
While Mercker was certainly a whining piece of crap in 2004, he was also a very good pitcher. He filled his role and did his job for the most part. Certainly for most of the season he wasn't the issue. Of course he played a major role in the Steve Stone/Dusty/Hendry/Cubs war so that goes against him.
Ryan Dempster 2005 5-3 3.13 ERA 93 IP 33 SV 1.435 WHIP 89 K 141 ERA+
In May 2005 the Cubs needed a closer, Dempster moved into that role after being a starter. Turns out Dempster was the right man for the job. He got 33 saves, and was one of the few bright spots on the 2005 Cubs team. A typical 2005 game would involve Derrek Lee bailing out the offense with a big homer and then Dempster ending the game by giving us all a heart attack. Still at least he got the job done.
Bob Howry 2006 4-5 3.17 ERA 76.2 IP 5 SV 1.135 WHIP 71K 146 ERA+
Lost in his awful 2008 season is the fact that Howry was actually really good his first two years with the Cubs. He shined out of the bullpen in 2006 despite being on the worst team in recent memory. Howry was signed in the offseason and immediately became the best relief pitcher on the Cubs.
Carlos Marmol 2007 5-1 1.43 ERA 69.1 IP 1 SV 96K 1.096 WHIP 326 ERA+
Everything I said about Prior and Harden times 1,000 for Marmol's 2007 season. He came up in 2007 and went from innings eater to go to seventh inning guy quickly. I've never seen such a good slider in my life, with the possible exception of K-Rod. Marmol shut down the opposition giving up 41 hits and just 11 runs in his 69 innings. Simply put, the best stuff I've seen from a pitcher the entire decade. So much fun to watch.
Kerry Wood 2008 5-4 3.26 ERA 66.1 IP 34 SV 84K 1.085 WHIP 137 ERA+
Kerry had to get some part on this team, after all he kind of the definition of a Cub. Kerry had a very good 2008 season and was possibly the best closer the Cubs had all decade. He had a number of memorable saves including a huge curveball strike 3 against Prince Fielder late in the season. It was probably Kerry's swan song as a Cub, and it was a fun ride.
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