50 Years of Failure

That's how long Cleveland professional sports teams have been losing:

This Saturday will mark the 50th anniversary of Cleveland’s last pro sports championship when the Browns beat the heavily favored Baltimore Colts 27-0 to win the NFL title, the last for the franchise and the city. Since then, the Browns, Indians and Cavaliers have gone a combined 141 seasons without winning it all.
That’s five decades. That’s 18,262 days. That’s a long time.
“It’s hard to believe,” Hall of Fame running back Jim Brown said. “Because when you look back at 50 years, something’s wrong, because somebody should’ve figured out something. ... We’ve got money and we’ve got a new building and we’ve got green grass and we can draft players, and we can’t do any better than that?”
Cleveland’s title drought is the longest for any North American city with three pro franchises. San Diego has gone 51 years since the Chargers won an AFL title, but the California city no longer has an NBA team and it’s a little easier to handle misery when it’s sunny and 70 most of the year...
It hasn’t all been bad. There have been a few magical seasons, they just didn’t end magically but with heartbreak. The Browns made it to three AFC title games from 1987 to 1990, but lost each time to Denver and quarterback John Elway. Two of those defeats have been given lasting nicknames: “The Drive” and “The Fumble.”
The Indians, who haven’t won a world championship since 1948, ended a 41-year drought by getting to the World Series in 1995 only to lose to Atlanta. Cleveland returned two years later but lost Game 7 in extra innings to Florida.
With All-Stars Mark Price and Brad Daugherty, the Cavaliers had some title-worthy teams in the 1980s that were stopped by Michael Jordan. They made it to the NBA Finals for the first time in 2007 but were swept by San Antonio...
 But on Dec. 27, 1964, when LBJ was in the White House and the Beatles had invaded America, the Browns ruled.
Facing a high-scoring Baltimore squad favored by double digits and loaded with future Hall of Famers like Johnny Unitas, Lenny Moore and Raymond Berry, the Browns won their first title since 1955. Wide receiver Gary Collins caught three touchdown passes in the second half from Frank Ryan, Lou Groza kicked two field goals and Cleveland’s defense pitched an unlikely shutout in front of 79,544 fans.
When he reflects on a game most Cleveland fans know only through black-and-white footage, Brown, who rushed for 114 yards, remembers one play vividly.
“My greatest memory of the game is Galen Fiss breaking through the line and tackling Lenny Moore for about a 7-yard loss,” the 78-year-old Brown said. “Galen was a real fine linebacker, but he wasn’t a great linebacker. But that day he played fantastic. ... After that I think, boy, what a great team effort. This is what team sports are all about.”
The Colts, coached by Don Shula, came in averaging more than 30 points per game. They were expected to bulldoze the Browns, who went 10-3-1 in the regular season under Blanton Collier and had nearly cost themselves a chance at the championship with a late-season loss at St. Louis.
However, they recovered by beating the New York Giants 52-20 to get to their first title game since 1957.

Even worse, it's not like the economy has been kind to Cleveland over this stretch.