Which MLB team has a big history, but has suffered the most in cases of losses, playoff heartbreaks, and other team problems.

CHANGE: To make this question tough, let's say "3rd most". Cubs and Red Sox are obviously 1-2.

Indians maybe. They were 2 outs away and blew it in 97. They were upset big time in the 54 WS. They were upset again in the 95 WS. They won the division 6 times in 7 years but failed to win the world series once. That's a bit of suffering. The Cubs would be #1 in my opinion.

Yankees

Either the Indians or Giants.

It's got to be the Braves.

18 playoff appearances and only 2 WS trophies to show for it.

The Cubs are the runaway winner, yes.

Third place? I'd go with the Giants. The Indians have had their setbacks, but never the individual talent to compare to some superstars the Giants have had -- Mays, McCovey, Perry, Marichal, Cepeda, Clark, and two generations of the Bonds clan -- and never to be graced with a championship.

(Yes, I know Mays was on the 1954 team. That was over a half-century ago, and he was quite young. No champagne during his monstrous peak years.)

The San Francisco Giants no doubt! They were 5 outs away in 2002 from winning the world series...they were up 5-0 with the game's best player at the time, Bonds, and they still lost. The team hasnt won a series since they moved to SF in 58. They have had two of the greatest superstars in the game in Bonds and Mays, no matter how you feel, they are great and they still couldnt manage to get a ring. SF has the games best fans besides Cleveland and perhaps Chicago and it hasnt worked out. They could have and should have won in 89' but the earthquake took the momentum and focus out. It has been just unlucky. They played in a dump before they got a new ballpark, they got screwed by not having the wild card in 1993, despite winning 103 games. And now of course, the media circus around Bonds (but its over now!). The Indians have struggled alot too...the Giants beat the indians in the 54' WS btw

The Braves have had a number of 1st round exits, so they would be up there, but my pick is the Indians. They lost 2 WS in the 90s, and the loss to the Marlins was particularly heartbreaking. Also, they lost to the Giants in '54 and were victims of one of the most unbelievable plays(Willie Mays overhead catch) in WS history.

yankees

First, the Cubs, hands down! They haven't won a World Series since 1908, (just three years--less than a thousand days--since the Wright Brothers flew their wooden plane). And they haven't even been to the World Series at all since 1945. They won the division a few times since then, but came up short.
Second, I wouldn't say the Red Sox; it would be the Indians, who haven't won the Series since 1948.
Third, would be the Giants (New York AND San Francisco), who haven't won the Seris since 1954.

the Braves....They won 14 divison titles during the 1990's 5 NL Pennants and only one World Series which was in 1995 they beat the Tribe 4 games to 2 Tom Glavine was the MVP.