- Drafted by the Los Angeles Dodgers with the fifth overall selection in 1968, only to have an injury-plagued 10-year Major League career with five different teams.
- Made his mark as a manager in both the U.S. and Japan, highlighted by a World Series appearance with the Mets in 2000 and a Japanese World Series title with the Chiba Lotte Marines in 2005, ending the team's 31-year title drought. The documentary The Zen of Bobby V (2008) was made shortly thereafter.
- Donned a sunglasses-and-fake-mustache disguise and returned to the Mets dugout after being ejected from a game in June of 1999, earning a three-game suspension.
- Joined ESPN as an analyst on Baseball Tonight in 2003 and returned in 2009. Named to the new Sunday Night Baseball broadcast crew for 2011.
- Claimed on a Food Network special to have invented the wrap sandwich (a filled tortilla) in the early 1980s at his Stamford, Conn., restaurant, Bobby Valentine's Sports Gallery Cafe.
- Named Director of Public Health and Safety for the city of Stamford in early 2011.
- Owns an extensive collection of baseball memorabilia, highlighted by programs from every World Series since 1912 except for the infamous 1919 "Black Sox" series.