In my lifetime (since 1997), the Chicago White Sox have made the MLB Postseason just three times: in 2000 (before I can remember) where they were swept in the ALDS in three games to the Seattle Mariners, in 2005, where they won the World Series over the Houston Astros, and in 2008, where they lost in the ALDS in four games to the Tampa Bay Rays. The White Sox have now missed the playoffs ten years in a row, with it being incredibly likely they miss for an eleventh straight time after this season.
It is important to note that just five of the fifteen American League teams could make the postseason until 2012 when the postseason expanded to a Wild Card Game, meaning six teams in the American and six in the National League made it. This means that the White Sox' futility is not as bad as some teams in the NHL or NBA, where half the league makes the playoffs. Even so, the White Sox have had just four winning seasons (2006, 2008, 2010, and 2012) in their last thirteen since the 2005 World Series win. That's painful.
I did not watch too much of the White Sox between 2013 and 2016, as I was jaded towards baseball after being cut from the freshman team in high school, but I know how poor they were during those years. Chris Sale, one of the best pitchers in the game, was the lone bright spot for many of those years before being traded to the Boston Red Sox before the 2017 season.
As the White Sox have continued to struggle to be competitive, the crosstown rival Chicago Cubs have put together their best stretch in franchise history, winning the 2016 World Series and making NLCS appearances in 2015 and 2017. For many Sox fans, this is just another tough pill to swallow as our friends, family members, and neighbors who cheer for the North Siders continue to enjoy their team's success while we wait for our chance to watch postseason baseball again on the South Side.
I've seen Sox players such as Gordon Beckham, Alejandro De Aza, and Dayan Viciedo start their careers for the franchise with incredible hype and short term results to back it up, only to underachieve in the long run. These are just some of the reasons why the franchise continues to fall short of October baseball. Pitching depth amongst starters and the bullpen over the last number of years contributes to this too.
The 2019 White Sox have shown incredible promise and improvement compared to last year's iteration, with the emergence of Lucas Giolito becoming a franchise ace on the mound, Eloy Jimenez's power-hitting, and James McCann's consistent batting average amongst other positives. While improvements have been made, the Sox are still not a playoff team and lack overall consistency in results. It's been fun to see the team trending upward, but the sudden regressions continue to depress me as a fan.
Some expect the 2020 White Sox to win the AL Central and be a playoff team, but it's still too early to tell. All I know is that the White Sox need to make it back to the postseason ASAP or this will become unbearable again.