I love sports. Always have and I probably always will thought I would say that my love of watching sports has gone down a little as I’ve aged. This kind of makes sense as I try to focus on my own accomplishments instead of those of others, not to mention I’ve gained a little more perspective on the universe and have found that games don’t really mean that much. Having said that, I find sports watching to be an experience, kind of a long, long story (especially when it comes to baseball) and what’s fascinating about sports as opposed to a fictional TV show, the ending isn’t always happy. In fact, more often than not it isn’t but it’s this lack of a happy ending that makes me want more.
It’s weird because if one had gone 20 years of watching a TV show before really getting ultimate payoff, people would get mad and let’s face it, the show wouldn’t really last. But I personally went that long before I saw my beloved Chicago Cubs win the World Series and the longer that took the more beautiful the payoff and the more addicting each season and each chase for the title became. Some seasons were great…some we’re not, most were not. Even though I’ve been a Cub fan throughout one of their best stretches during the post 40’s, there’s still been more bad than good. Having said that, each season has brought me memories and even with the championship there are still times I miss the good old days. I figured I’d rank every Cubs season since I’ve been a fan because I like to think about this shit. I find “fan stories” to be the most interesting part of being a fan because the emotional attachment to rich, adults playing games is a weird thing but it’s something I possess and I’m happy that I do. Anyways, here’s my ranking of Chicago Cubs seasons since I was a tiny person. I’m going to do this in reverse to build suspense but it’s obvious what number 1 is going to be.
2000 Cubs-65-97-I honestly have no memory of this season. I’m sure I watched them play but I have no idea if anything of not happened off the top of my head. After looking it up, this was the year the Cubs played the Mets in the Tokyodome and I do remember waking up at 3 in the morning to listen to each game on the radio. The Cubs won the opening game and I remember being stoked that we we’re going to win everything. The Cubs did not win everything.
2011 Cubs-71-91– This team was no fun. They had no young players and the memories of the 07 and 08 teams that made the playoffs were very distant. At this point it felt like there was no future to this team but then they fired Hendry and Theo Epstein happened. The 2011 offseason was fun as hell.
2006 Cubs 66-96-Dusty Baker was a horrible manager that played Neifi Perez too much. Derek Lee had a season ending injury early in the year just a season after practically dominating baseball. The only real highlight was a Michael Barret grand slam, like, 2 games into the season against the Cardinals. Then the dumb Cardinals won the World Series with a bad team. This year was no fun.
2010 Cubs-75-87-This team was boring. Um, they signed Marlon Byrd and the Cubs played at Fenway, which would have been more useful 7 years later. I guess Ted Lilly got traded for Blake DeWitt and I got excited to watch his first game solely because Blake DeWitt hit homers all the time on me on MLB: The Show. He did not do this in real baseball.
2013 Cubs-66-96-This was the 4th straight losing season and it was painfully obvious that Theo Epstein didn’t want this team to win so he could draft more baseball players. They did draft Kris Bryant and that was cool.
1999-67-95-Cubs-I was a kid and didn’t understand how baseball worked. The Cubs got kind of lucky in 1998 when they made the playoffs but I thought they were building something. They weren’t, they were a bunch of old players that weren’t really good and they played like it.
2002 Cubs-67-95-2001 was kind of magical and was also like 1998 where the team was a bunch of mediocre old dudes who made a playoff run. 2002 was, again, when those old dudes played like old dudes. I’m sure Sammy Sosa hit some home runs, which was fun and I know Mark Prior made his debut, which was awesome….until the Mark Prior bad things happened later in his career.
2012-Cubs-61-101-This team sucked and we knew they’d suck. We accepted that they would suck and were fine with it because the Cubs had a plan for the first time in ages. The plan was not exciting in year one though and the highlights of the season for me were getting drunk on opening day (which Kerry Wood blew. I still get angry about this an I don’t really know why) and getting cheap tickets to Wrigley because nobody cared about the 2012 Cubs.
2009 Cubs-84-77-This team wasn’t really bad but they certainly didn’t live up to expectations and even though they led the division late in the season, it never felt like this team was going to even make the playoffs. Plus, I had to root for Milton Bradley who was a terrible underachiever and as it turns out, a terrible, terrible person.
2005 Cubs-79-83– I weirdly liked this team. They weren’t really good and were never in the thick of things and they traded Sammy Sosa, who is my favoritist player ever and I will justify his PED use forever because he did it in the Dominican I’m sure and that’s no really wrong. I liked Jeromy Burnitz, mostly because he was a lefty with power and I was a lefty who once read Nintendo Power? I don’t know. Cool things did happen, like Maddux striking out some dude for some mile stone, but weird things happened, like oft injured Kerry Wood coming out of the bullpen for no reason, because the front office thought they kind of had a chance to get a playoff spot down 7 games in late August. Oh, and the White Sox won the World Series, which I don’t care about now but at that age I hated the South Siders so I wanted to throw up I guess.
2014 Cubs-73-89-This was another bad season during the rebuild but there were exciting moments, like Baez coming up along with Soler (Soler wasn’t good but at the time it was a cool thing.) This team started off slow but for the last 4 months played .500 baseball, which was really exciting considering the previous seasons were so terrible. Light could be seen at the end of the tunnel and I started to daydream that the playoffs were around the corner.
2004 Cubs 94-68-This team should have been good (and actually there record is way better than I remember). The Cubs getting Nomar Garciaparra was the coolest thing ever because they rarely got the big name player. There were some cool games this season too, like in April or May when Alou and Sosa went back to back to walk off the Reds or when Todd Walker Super Man slid into home to beat the A’s (look, I remember random regular season games, it’s what I do.) But then this team blew a playoff spot the last week of the season because some random Mets nerd hit a home run. This team had a bunch of unlikable dudes on it anyways, like Kent Merker who decided he would be mad at announcers and then the infamous moment where Sammy Sosa took off one of the last days of the season ending with the tragic breaking of Sammy Sosa’s boombox, likely by Kerry Wood.
2007 Cubs–85-77 Lowest rated playoff team. There were plenty of cool things this team did, like come from behind to beat the Brewers for the division. But this team was also so frustrating at times. They got off to a slow start and I went into “bad Cubs, I won’t watch much mode” for a good part of the season. The last half of the season was fun enough that I would have this team rated higher except for the playoffs were so boring as they got swept by the D-Backs.
2015 Cubs 97-65-This team should be higher. The playoffs were really fun, especially following the sweeps in previous years. This was also the best Cubs team I had seen up until this point and it seemed like every week a new, top prospect was coming up. Jake Arrieta pitched one of the best stretches in MLB history but the entire season I felt fear that because they were destined to play in the one game Wild Card playoff, that all the fun would be sucked away in one game. Instead they won that game then beat the Cardinals in the playoff series (a series that kind of marks a big turn in the rivalry) but because I lived the season in fear, I kind of missed out on a cool season.
2008 Cubs-97-64-This season was so much fun. Yes, the Cubs were expected to compete but they dominated the majority of the season. For the first time in my life the Cubs were the best team in baseball (technically, it was the national league but they felt like the best team in baseball.) They ran away with the division, which seemed impossible, and there were so many memories from this year but I think my favorite was Jim Edmonds going from my most despised player to one of my favorites. The only thing that sucked about this year was the playoffs when they got swept. If there was a past Cubs team that I wish could have won a title (aside from the 2016 team, who was fun and deserved it) it would have been this one.
2001 Cubs-88-74-It’s weird to have this team so high but the fact is there’s a lot of nostalgic factor to this one. This is the first season I remember watching so many games with my dad and I loved doing that daily. The season itself was special, just because the Cubs had no right to be in the playoffs, yet for a majority of the season they led the division by many games. As I look back, that team was pretty much Sammy Sosa having one of the best years ever and a bunch of random guys who also played baseball. I could probably name this entire team from memory and always have been disappointed they didn’t quite make the playoffs. This season did feature the Steve McMicheal game, where he verbally threatened the umpire and got ejected following the national anthem, which was weird as hell. The ending of this game was weird too, look it up on youtube if you wanna.
2003 Cubs-88-74-5 fucking outs. This team almost did it. Even with the Cubs finally winning one, this season hurts.
1998 Cubs-90-73-This is the year I became a Cub fan. I had a TV in my room and would sink up the radio to the TV when the games were on the TV I had (I didn’t have TV.) I went from liking a bunch of teams to having to watch the Cubs every day. Sammy Sosa chased the record and the one game playoff win over the Giants still sticks with me.
2016 Cubs-103-58-Dude, they won the World Series.