1. Dallas Cowboys » Can’t argue with their popularity. The Cowboys are “America’s Team” for a reason. That massive fanbase gets them on NBC or ESPN multiple times a season. But they have won just two playoff games since 1996 and have not reached the NFC Championship game during that 15-year stretch.
2. New York Knicks » Since its heyday in the late 1960s and early 1970s, the Knicks have played for the NBA title as many times as … the Nets. Twice. And even during their 1990s “renaissance” — two NBA Finals and two Eastern Conference finals appearances in eight years — they virtually ruined the league with their loathsome style of play.
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3. Washington Redskins » It’s too bad the NFL offseason is in complete flux thanks to the impending lockout. Because this is the Redskins’ time of year. How are they supposed to unfurl their “Offseason Champions” banner now? The fanbase somehow remains in tact. But it’s been 20 years since the Redskins were relevant.
4. Toronto Maple Leafs » If there’s even a whiff of success in Toronto you would think a dynasty was on the way. There was a mini-riot in Ontario last fall when they started 4-0. How’d that work out? Toronto will miss the playoffs for a sixth straight year, has not reached the Stanley Cup finals since 1967 and made the conference finals just four times in 43 years.
5. New York Mets » Once the mid-’80s Mets imploded, it’s never been the same. Yes, they won a division title in 2006 and also made the playoffs in 1999 and 2000 as a wild card. But New York finished below .500 11 times since 1990. All that despite one high-profile, free agent signing after another from Bobby Bonilla to K-Rod.