A Brief History of the Cubs
But the Cubs spent over a century without a world series win and somehow managed to make a brand out of having loyal fans who would turn out every week to watch their team lose, and they made bank doing it.
Not the case! Let's look at the actual history of the ballclub between 1906 (their first WS appearance) and 2016 (their latest) and see when and why they "made bank".
The 1906-1908 team was a juggernaut - they simply had the best ballclub in the NL during this stretch and all that winning created a loyal fanbase, but you'd have to be a fool to think those 3 years paid for the next 108. The Cubs went to the World Series 7 times between 1910 and 1945, and that stretch created the first two generations of Cubs fans who would continue to pass the tradition down through the family (and through extended neighborhood families, as well).
Between 1945 and 1980, the Cubs had a lot of ups and downs, but never got over the hump in the good years, the most iconic being 1969 when a worn-out Cubs squad was eventually overtaken by the Miracle Mets. 1969 did pay for the next decade's worth of player salaries until the Wrigleys called it quits and sold out to the Tribune Company in 1981, which had been the Cubs' broadcast partner for decades via WGN radio and eventually WGN-TV.
The Tribune, being a media company, had no idea how to run a ballclub, but they did understand marketing, and so they hired carnival barker Harry Caray away from the White Sox and started to concentrate on everything except the product on the field, which was still pretty bad. Harry brought his "Take Me Out to the Ballgame" audience sing-along schtick along with, and the focus shifted from the Lovable Losers to Iconic Wrigley Field. You stopped hearing so much about player stats and instead got to see the scenes around the neighborhood, including some crazy kids who brought lawn chairs and coolers up onto the roofs of nearby apartment buildings to watch the game without paying for a ticket. Individual moments of greatness on the field were highlighted, but the overall picture was overlaid with one long Budweiser commercial and frequent camera shots that lingered on leggy coeds in the stands.
And all of this was broadcast worldwide thanks to WGN-TV being a superstation with a satellite uplink. Hundreds of thousands of children across the country would come home from school and flip through the channels only to find the late innings of a Cubs game still going on, and the Cubs had a new fanbase that thought of the team as more a reason to party in Wrigley than a serious baseball product. Sure, there were good years (1984, 1989, 2003), but the Tribune-era Cubs weren't so much about the results, but rather as a marketing vehicle for the Trib.
When the Trib started to lose money hand over fist, they had to sell, and in order to do so, they actually improved the product on the field. They stocked up on expensive free agents in 2006-2007 and had just enough winning baseball to convince the Ricketts family to buy this confusing thing away from them and let them concentrate on losing money in media.
The Ricketts had bought the team in a fit of hubris, remembering the Harry Caray lessons of beer-and-ballpark, but soon understood that this wasn't good enough. They had to actually put a quality product on the field to put asses in seats. Right before the recent renaissance, I took a long vacation in Chicagoland and went to as many games as I could squeeze in. They had a 10-game homestand in summer 2014, and I wasn't able to make it in for the first game. But I went to 8 of the other 9, and I walked up to the ticket window right before the game and paid face for most of those tickets. The place was dead enough that I actually met Tom Ricketts on one of his laps through the stands. There would be very little chance of that happening in any of the years since.
TL;DR: The Cubs were Actually Good for 4 decades, coasted on that for another 3, were recreated as an excuse for a tits-and-beer theme park, but eventually had to start winning games again in order to pay for the new owners' egos.