#1 2012 (2-14)
Fun fact: 2012 was the first season that I remember watching from start to finish in my Chiefs fandom. It's safe to say that I was not a happy camper that Fall and Winter.
What unfolded that year was nothing short of an utter catastrophe. It's difficult to pinpoint where to even begin. Romeo Crennel proved to be ill-suited for the role of an NFL head coach. The team endured the worst record in the league, finishing at 2-14, and possessed the lowest-scoring offense. They also tied for the most giveaways in the NFL with 37. Matt Cassel's tenure with the Chiefs had reached its nadir, and the subsequent replacement, Brady Quinn, failed to bring any improvement. The team suffered double-digit losses a staggering ten times that season. Ten. Despite securing a victory in Week 3, the team did not hold a single lead in regulation until Week 10, when they faced Pittsburgh.
Off the field, fans resorted to wearing black at games as a form of protest against the team's abysmal performances. Furthermore, an airplane flew a "Fire (Scott) Pioli" banner over Arrowhead Stadium on game days, reflecting the frustration with the team's management. Tackle Eric Winston, rightly so, publicly criticized the fans who cheered when Matt Cassel left the Week 5 loss against Baltimore due to a head injury. Tragically, the season was further marred by the Jovan Belcher tragedy on December 1.
There isn't much more to be said about this woeful season, but it's worth noting some redeeming aspects. Given their status as the worst team in the NFL, the Chiefs held the coveted #1 overall pick in the 2013 NFL Draft, which they used to select left tackle Eric Fisher. Additionally, they went on to hire Andy Reid, who has since brought remarkable success to the franchise. Despite only winning two games, the Chiefs had an impressive six players named to the Pro Bowl that season: Jamaal Charles, Derrick Johnson, Justin Houston, Eric Berry, Tamba Hali, and Dustin Colquitt. It's worth noting that it's quite rare for a team with just two wins to have such a sizable Pro Bowl representation.
The 2008 Chiefs ranked tied for last (out of 60) in Win % and were dead last in both Point Differential per Game and SRS.