Four. Elston Howard played in 9 World Series with the Yankees (1955, 1956, 1957, 1958, 1960, 1961, 1962, 1963, 1964) and was on the winning team 4 times (1956, 1958, 1961, 1962).
No the losing team does not get a world series ring.
The winning player's share in the 2008 World Series was $351,504, the losing player's share was $223,390
The Pittsburgh Pirates were the losing team in the 1903 World Series.
The Losing player's share in the 2009 World Series was $265,357.50, the winning player's share was. $365,052.73
The Pirates have appeared in 7 World Series, losing 2.
39% of teams losing game 1 have gone on to win the series.
It has never happened in the history of the World Series.
Boston Red Sox pitcher, John Lackey, was the losing pitcher in Game 2 of the 2013 World Series.