And players that make more than entire teams and not able to win. Was Sheffield on the 2001 team when they lost? No, he was with the Dodgers.
04 Yankees-lost to Bosox in ALCS
05 NYY-didn't make it to the ALCS
06 NYY-lost in ALDS to Detroit
He has great hitting but he obviously couldn't do enough to help them win the big one. Their payroll should bring a World Series appearance almost every year but it doesn't. Sheffield's contract caused problems for the Yankees and he is pissed that a Latin player took his job with the Yankees. He could have stayed if ye played first base but his ego couldn't take it. He would be better and quicker in the infield than Giambi or other players but he couldn't suck it up. What a great teammate.
In baseball, a single player has less impact on his team winning a series than any other sport. The burden is on the team as a whole. Many Yankees had poor playoff performances lately, most notably the pitchers.
What problems did Sheff's contract cause? Did it prohibit the Yankees from obtaining talent? No. Also, Sheff wasn't being given the option to play first this year. That was an experiment the Yankees weren't willing to continue this year. FWIW, Sheff offered to play infield on multiple occasions to help when a player was injured. Yes, I still think he's an asshole, but he plays to win.
As for payroll bringing home a WS title every year, that's absurd. Yes, a high payroll should get a team to the playoffs consistently, but winning the WS is a crapshoot after that. Short series in baseball are the equalizer - there's a greater chance for a lesser team to win a playoff series than in other sports, for a variety of reasons. Playoff wins have as much to do with timing and luck as they do talent.