I was born and raised in the area, gaining an awareness of sports in the early 70’s. From that point on, we had to learn “losing builds character” and therefore our sports teams generally had the most character of any in the nation.
The Tribe was routinely terrible. This was during the Gabe Paul & Phil Seghi years. To give you an idea of how bad the teams were, they only had 4 winning seasons from 1969 until 1994. Out of those, their highest win total was in 1986, when they went a whopping 84-78. This prompted Sports Illustrated to pick them as their dark-horse favorites for 1987, when they promptly went 61-101. In 1976, Wayne Garland won 20 games with the Orioles. The Tribe offered him what was at the time an obscene contract in free agency: 10 years, $2.6 million. While he put up decent numbers (albeit on the way to losing 19 games) for them in 1977, he hurt his arm and would never again win more than 6 games before being out of baseball after a brief stint in the minors in 1982. The Tribe was still paying him four years later. The Indians haven’t won the World Series since 1948.
As for the Cavaliers, everyone is familiar with their meteoric rise after LeBron James joined the team. What fewer people are aware of is just how historically awful they were back in the day. For three seasons, 1981-1983, the team had what is often referred to as the worst owner in sports history: Ted Stepien. He was so bad, the NBA made a rule NAMED after him to prevent someone being quite so awful in the future; the Stepien Rule prevents a team from trading consecutive first round picks, one year after the other. Stepien had traded away FIVE in a row, in addition to other picks (noteworthy misses thanks to these trades include James Worthy, Dennis Rodman, & either Charles Barkley or John Stockton). The per diem checks players get for their food on the road would occasionally bounce. Yes, he was that bad. So in 1989, under the leadership of a new owner (Wayne Embry) and coach (Lenny Wilkens), the Cavaliers had what many felt was a championship-caliber team. This, of course, led to The Shot. That said, at least the Cavaliers finally brought home a trophy.
And then come the Browns. A very strong team from the 40’s to the early 70’s, the Browns stumbled their way through the Disco Decade until a flash of success in 1979 and 1980, as Brian Sipe came out of ignominy and lead a bunch of players nicknamed “The Cardiac Kids” to winning records in each season, including a total of 8 come-from-behind wins in the 4th quarter. Still, 1980 will always be remembered for a foolish play call in the playoffs against the Raiders: Red Right 88: where as time was winding down and the Browns were only down 12-14, they didn’t kick the field goal from the 12 yard line. Instead, a pass play was called and led to an interception which clinched the game. Random aside; afterwards, my grandfather’s doctor forbade him from watching any Browns games on TV. And yes, that’s a true story. Eventually, the Browns would luck into getting Bernie Kosar in the supplemental draft (thanks to machinations of both the team and Kosar). However, that luck never extended to the final results.
In Kosar’s rookie year, 1985, the Browns managed to win the division with a lowly 8-8 record. While Kosar struggled as rookie QB’s often do, they featured two running backs who ran for over 1000 yards that season, the second* time it had happened in the NFL. In the playoffs, they squared up with Dan Marino’s Dolphins, and were beating them 21-3 in the 3rd quarter. They wound up losing, 21-24.
Then came The Drive the next season.
The Fumble the season after that.
They left and became the Baltimore Ravens 9 years later, in early 1997.
The “New” Browns came into being for the 1999 season.
The Browns have never been to the Super Bowl, let alone won. This iteration of the team has had only 2 winning seasons in 19 years.
So yeah, heartache is a constant companion for Cleveland sports fans, but damn do they have character.
*edit- thanks, Mark!