We know them, the ones who are hyped, have lots of good players but on the big stage they fail more often then not.
Here are my offerings
England Football
Indian Cricket team.
Compared to the expectations of their owner(s) and fans, and their payroll, I’d say the Yankees since 2000.
Toronto Maple Leafs haven’t even made a Stanley Cup final in over 40 years.
The Brooklyn Dodgers.
This was a collection of stars that choked every October, but were somehow perceived as lovable underdogs, rather than as underachievers.
Chicago Cubs. With their huge fan base, their full stadiums, their revenue, and their spending it is pathetic that they haven’t won a World Series in 100 years. Good thing their fans would rather go to the largest bar in Chicago rather than have a successful team.
Can we set up some guidelines? I think there’s a difference between doing well and choking away a good opportunity (like the Philadelphia Eagles 
or that recent Seattle Mariners team that won close to 200 games or so) and just always being mediocre despite every reason to excel…
That said, where would the recent Mets rate? They certainly choked away a playoff spot or two recently, but with their payroll and team, they should be doing well enough to at least choke in the playoffs. The Cubs are a good answer. The Knicks are just pathetic, their expectations are too low for them to underachieve. Or the Washington Redskins, who spend tons of money and always pick up a top free agent but never seem to go anywhere.
The bold is the intention of the OP.
:smack:
How could I forget, the San Jose Sharks.
:mad::mad:
The Los Angeles / California / Anaheim / Los Angeles of Anaheim Angels have had megabucks income for decades, spent freely on big-time players, and have won the World Series exactly once.
They’re probably worse than the 1990’s Atlanta Braves, who always had the best pitching in baseball and always won their division, but almost always politely left the party in the early rounds.
If you only judge the Yankees by whether they win the World Series, then yes, they have underachieved, but I think that’s a little unfair. They’re perennial playoff contenders, which a normal fanbase would consider to be the hallmark of a successful team.
In the last 5 years I’d say the San Diego Chargers have been underachievers. They get hyped every season because their offense looks so powerful on paper, but something seems to derail them every year. They will probably dominate a weak AFC West this year and be overrated heading into the playoffs.
The Washington Redskins in the Daniel Snyder era. They keep signing big name once great but now over-the-hill guys for WAY too much money and giving up their young home grown talent in the process. This trait seem not be limited to players but coaches too. (…or, what Jules Andre said smack)
Yeah, but the OP said "lots of good players ", so the Leafs haven’t qualified for that for a long time.
I’d have to go with the Atlanta Braves.
All Blacks, South Africa Cricket, Duke basketball (lately)
I’d vote for the Oakland Raiders, but they’ve been circling the drain since Gruden left and their roster doesn’t feature many players of note. The Cowboys, OTOH, have been underachieving for some time, despite having marquee players.
After how much failure do you have to conclude the players really aren’t all that good anyway?
My football/soccer team took 104 years (1883-1987) to win their first - and still only - major trophy. The FA Cup. I believe it is still the only final they have been in.
Despite being in the top division in England for IIRC 30-odd years they never finished higher than sixth and only rarely in the top half of the table (for most of that period there were 20-22 teams in the league).
Edit:
Forgot about the “good players bit”. I just found the whole “haven’t been in a final for 40 years” thing weird. I get the same feeling when I read “Fever Pitch” or listen to Nick Hornby talk about Arsenal. All the moaning about ten years without a major trophy or something. It took us 104 years. 104! And it has now been 32 years since that!
Sorry, make that 22 years.
I, honest to God, have a Maths degree as well. In my defence it is Pure Maths, so it is all Group Theory and Topology. But still …
The New York Knicks might play in the basketball capital of the world, but they only have two championships in their history. The latest was in 1973. In recent years they’ve been especially terrible.
San Diego Chargers in recent years.
But their payroll and on-paper talent is so immense that merely being in contention for the playoffs is underacheiving.