David Ortiz won plenty of times with the Red Sox. He led Boston to a World Series victory in 2004 after an ALCS in which he initiated the first-ever 3-0 comeback in the history of baseball. He won two more World Series titles since then, including in 2013, when he batted .688 throughout that series.
Red Sox
The Red Sox look a lot different since Ortiz retired from the game, and they have since tried to find new ways to win. One of these ways is by trying to get as much bang for their buck as possible through relying on homegrown talent and short-term contracts, a strategy that has worked for the Tampa Bay Rays.