The Simpsons is full of quietly heart-breaking characters, with the town grinding down remarkable people and being the home for broken families. But one of the quietly saddest is also one of the most unexpected, especially considering how often this C-list character is used for laughs.
Let's look at what the reveal that Hans Moleman being the former be Mayor of Springfield says about the small town and how it makes him an even more tragic character.
Hans Moleman is one of the elderly citizens of Springfield. More so than perhaps anyone in the town, Moleman is perpetually unlucky. He is shown to occasionally have a family but is more often portrayed as a lonely old man, working various odd jobs around Springfield to keep himself afloat. His frailty and near-constant string of bad luck have resulted in his apparent death multiple times over the years -- with fans often comparing him to the similarly death-prone Kenny McCormick from South Park. Moleman is always later seen in the town, fully restored from whatever injury he just suffered, always bemoaning his lot in life. However, this wasn't always the case for Moleman.
In his younger years, he was a far more popular and influential figure in Springfield. In fact, Season 26's "Walking Big & Tall" revealed that thirty years previously, he had actually been the Mayor of Springfield. An athletic and energized public servant, Moleman was -- similar to Mayor Quimby in the present-day -- quick to use flashy distractions to placate the citizens of his town. For Moleman, that involved buying a song and passing it off as a unique anthem for Springfield to take pride in. He had no genuine expectation in his citizens, admitting later in life that he never thought his ruse would be discovered because he doubted anyone would ever truly escape the simple grasp of their small hometown.
But unlike Quimby -- who has proven to be comically corrupt and selfish over the years -- Moleman seemed genuinely invested in the betterment of Springfield. He was elected to four terms, and he balanced the budget for the town multiple times. Flashbacks to earlier years of Springfield suggest the town was once a more optimistic place than it is now, with the Season 5 episode "$pringfield" highlighting how the Springfield of decades past was full of the exciting new industry -- even if it was short-sighted investments, such as in an "aqua-car" factory. It was during these earlier decades that Springfield was a more natural and relaxed place -- and a far more stable town. If Moleman was balancing the budget so consistently, it would explain the relative gleam of Springfield.
However, the town has fallen on hard times in the years since. On top of many investments from Springfield failing to pay off, the arrival of Mister Burns could also be seen as impacting this side of Springfield. The cruel and selfish tycoon was initially welcomed into Springfield with open arms, as remembered by Homer in Season 24's "To Cur With Love." But Burns quickly used his wealth to place a stranglehold on the town and more or less become the most feared and powerful man in town. The ensuing deterioration of Springfield's economy -- which has been the subject of multiple episodes, and as in "$pringfield" sometimes results in Burns controlling even more of the city -- could have been why the popular mayor was eventually voted out of office.
In a way, Moleman can be seen as the physical representation of what has happened to the small town of Springfield over the years, bleeding into the modern-day -- where families like the Simpsons try to navigate an often hopeless town to find some chance for a better tomorrow. Moleman was, years ago, a vibrant and bouncy man. But in the end, he was just another part of Springfield's long-running history of disappointment. The former mayor is now just another faceless schmuck, who most of the town -- and even his rarely seen family -- barely notice at all. In the end, this revelation made a minor joke character into one of the saddest players in the ecosystem of Springfield.