Valentine was born in Stamford Connecticut to Joseph and Grace Valentine. Valentine was recruited out of Rippowam High School in Stamford, Connecticut by the University of Nebraska, Duke University, the University of Notre Dame and the University of Southern California as a star in football and baseball. He attended USC where he became a member of the Sigma Chi Fraternity. The Los Angeles Dodgers drafted him number five overall in the 1968 Major League Baseball Draft.
After winning the Pioneer League's MVP award with the Ogden Dodgers in 1968, Valentine debuted with the Dodgers as a September call-up in 1969 at 19 years old. Though he never recorded a major league at-bat that season, he did score three runs as a pinch runner.
Back in the Pacific Coast League for 1970, Valentine was again his league's MVP after batting .340 with fourteen home runs for the Spokane Indians. Led by Valentine and manager Tommy Lasorda, Spokane won the league championship over a legendary Hawaii Islanders powerhouse.
Valentine made the Dodgers out of Spring training in 1971, and batted .249 with one home run and 25 runs batted in. The following season, he managed to play in 119 games by playing many different positions—including shortstop, second base, third and all three outfield positions. His batting average improved to .274 in 1972, but he was not showing his early promise as a major leaguer, and following the season, he was packaged in a trade along with Frank Robinson, Billy Grabarkewitz, Bill Singer and Mike Strahler to the California Angels for Andy Messersmith and Ken McMullen.
Valentine batted .302 his first season with the Angels before falling victim to a multiple compound leg fracture at Anaheim Stadium when his spikes got caught in the outfield's chain link fence while attempting to catch a home run ball hit by Dick Green. Valentine missed the remainder of the 1973 season and Valentine never regained his speed. In 1974, Valentine made 414 plate appearances in the utility role, the second most of his career, and batted .261 with three home runs. At the end of the 1975 season, he was traded to the San Diego Padres.
Valentine only appeared in 66 games for the Padres when he was part of New York's infamous "Midnight Massacre." On Wednesday, June 15, 1977, the New York Mets traded Dave Kingman to the San Diego Padres for minor league pitcher Paul Siebert and Valentine, sent Tom Seaver to the Cincinnati Reds for Pat Zachry, Doug Flynn, Steve Henderson, and Dan Norman, and Mike Phillips to the St. Louis Cardinals for Joel Youngblood.
Valentine's role with the Mets became even more limited, and he was released in spring training, 1979. He signed with the Seattle Mariners shortly afterwards, and made his debut as a catcher that season. Following the season, he retired from baseball at 29 years of age.
Valentine was serving as water boy for the Mets when he was tapped by the Texas Rangers to take over managing duties from Doug Rader 32 games into the 1985 season. He was not able to turn the team's fortunes around right away and the Rangers went 53–76 the rest of the way, finishing with an overall record of 62–99. The following season the Rangers finished second in the American League West with a record of 87–75. Valentine also finished second for AL Manager of the Year that year. Hopes were high in Arlington after the 1986 season, but his Rangers fell back into sixth place the following two seasons. Unable to replicate his early success, Valentine was fired by managing partner George W. Bush halfway through the 1992 season with a record of 45–41. Toby Harrah took over as manager, and led the Rangers to a 77–85 record and a fourth-place finish. He finished his Rangers' managerial career with a record of 581 wins and 605 losses with no post–season appearances.
In Texas Rangers, while still manager of the Rangers, Valentine worked as an on-the-field analysts for NBC's 1989 ALCS coverage alongside Bob Costas and Tony Kubek.
In 1994, Valentine managed the Mets' Triple-A affiliate, the Norfolk Tides. Bobby led the Tides to a 67-75 record, which was good for fourth in the five-team West Division of the International League.
In 1995, Valentine began his first stint as manager of the Chiba Lotte Marines in the Japanese Pacific League. That season, the team surprised most Japanese baseball fans by finishing in second place (69–58–3), a remarkable feat for the Marines who had not won the Japanese Pacific league pennant since 1974. However, he was fired abruptly due to the personal conflict with general manager Tatsuro Hirooka, despite having a two-year contract.
Bobby returned to the U.S. and the Norfolk Tides in 1996, managing them to an 82–59 record and second place in the International League's West Division. He then was promoted to manager of the Mets with 31 games left in the 1996 season, and led them to a 12–19 record the rest of the way.
Over the next two seasons, with Valentine at the helm, the Mets began a resurgence, finishing 14 games over .500 (88–74) both years. Valentine's most memorable game as a manager occurred on June 9, 1999. In the 12th inning of a 14 inning marathon with the Toronto Blue Jays, Mike Piazza was called for catcher's interference on Craig Grebeck. Valentine was ejected by home plate umpire Randy Marsh for arguing the call, and returned to the dugout an inning later in a disguise (a fake moustache). Unamused, Major League Baseball fined Valentine $5,000 and suspended him for two games. The Mets went on to win the game 4–3.
Valentine led the Mets to a record of 97–66 and a wild card playoff berth that season. The Mets beat the Arizona Diamondbacks in four games (3–1) en route to the National League Championship Series, where they eventually lost to their division rival the Atlanta Braves in six games (4–2).
In early 2000, Valentine was at the center of what would be called "The Whartongate Affair," in which he allegedly mentioned to students at the University of Pennsylvania's Wharton School of Business somewhat cynical, insider comments regarding a handful of Mets players and the organization as a whole.
The Mets returned the following season, finishing the year with a 94–68 record and another wild card playoff berth. This time, the Mets would not be denied the pennant, winning the 2000 National League Championship Series by defeating the St. Louis Cardinals in five games (4–1). The Mets run would end during the 2000 World Series as they were beaten by their crosstown rival New York Yankees in five games (4–1).
Valentine won the 2002 Branch Rickey Award for his donations and personal work with survivors of the September 11 attacks. Valentine had an uneasy, if not volatile relationship with general manager Steve Phillips, who fired three of Valentine's coaches and selected the replacements himself during the 1999 season (in a move many observers felt was an attempt to get Valentine to quit) and eventually fired him after the 2002 season. Valentine was hired by the network soon afterwards. He finished his Mets managerial career with a record of 536 wins and 467 losses.
In 2004, Valentine began his second stint as manager of the Chiba Lotte Marines. On October 17, 2005, he led the Marines to their first Pacific League pennant in 31 years after emerging victorious in a close playoff with the Fukuoka SoftBank Hawks. Nine days later on October 26, the Marines won the Japan Series in a four-game sweep of the Hanshin Tigers for the first time since 1974. On October 27, 2005, Valentine issued a challenge to the World Series champion Chicago White Sox on behalf of the Chiba Lotte Marines. Valentine called for a seven-game World Series to be played between the American and Japanese championship teams. Unlike the World Baseball Classic, a competition featuring sixteen national all-star teams, a World Series-styled tournament between the winners of both the American and Japanese championships has never been played.
Following their Japan Series championship, the Marines won the inaugural Asia Series by defeating the Samsung Lions of the Korea Baseball Organization in November 2005. In 2008, Valentine was the subject of the ESPN Films documentary "The Zen of Bobby V." The film followed Valentine and his 2007 Chiba Lotte Marines team. "The Zen of Bobby V." was an official selection at the 2008 Tribeca Film Festival. The Marines decided to let Valentine go after the 2009 season after an extensive smear campaign led by club president Ryuzo Setoyama, which ironically backfired and resulted in an overflow of support for Valentine by local fans. In the end, Valentine was fired, even though a petition to extend his contract was presented to the organization with 112,000 signatures.
Valentine accepted a position as a baseball analyst for ESPN. He had previously appeared on the cable network's Baseball Tonight show in 2003. He made his broadcasting debut for the 2009 American and National League Championship Series and World Series.
In late 2009, Valentine was a candidate to replace Eric Wedge as manager of the Cleveland Indians, however the job went to Manny Acta.
Bobby continued working with ESPN for the 2010 MLB season. He was interviewed for the Baltimore Orioles managerial position after manager Dave Trembley was fired in early June; Valentine later withdrew his name from consideration. Valentine was considered a front runner for the Florida Marlins managerial position that opened after Manager Fredi Gonzalez was fired in late June. However, Valentine confirmed he was no longer a candidate for the position after the Florida Marlins owner, Jeffrey Loria stated that Edwin Rodriguez, the interim manager they summoned to replace Gonzalez, will manage the team through the 2010 season. With the firing of the New York Mets Manager Jerry Manuel at the end of the 2010 season, Valentine had been speculated by the local New York sports media of returning to the team. It was also reported that the Toronto Blue Jays and Seattle Mariners had interviewed Valentine for their open managerial job.
Valentine was interviewed by the Milwaukee Brewers for their managerial opening in October 2010. He was believed to be a finalist along with Bob Melvin, Joey Cora, and Ron Roenicke. The position eventually went to Angels bench coach Roenicke.
On December 1, 2010, Valentine, Orel Hershiser and Dan Shulman were named as ESPN's new Sunday Night Baseball crew for the 2011 MLB season. As recently as June 19, 2011, news outlets reported that Valentine was once again a candidate for the Florida Marlins managerial position after the ballclub free fell in the standings. That did not come to fruition, however, as the Marlins hired former White Sox manager Ozzie Guillen.
On November 21, 2011, Bobby met with the Boston Red Sox for a formal interview for the open manager's position, and on November 29, it was reported that he would be the new Red Sox manager and the successor to Terry Francona. Valentine was introduced by Red Sox General Manager Ben Cherington on December 2, 2011, and chose to wear number 25 in honor of the late Tony Conigliaro, with whom he briefly roomed during spring training 1976 with the San Diego Padres.
Valentine's first and only season with Boston was marred by injuries, in-fighting, clubhouse drama, public disagreements with players, and a tumultuous relationship with his fellow coaches. Under Valentine's management, the 2012 Red Sox finished 69–93 (last in AL East), their worst record in 47 years. Valentine was fired by the Red Sox on October 4, 2012, just one day after the conclusion of the regular season.As of November 21, 2014
On February 22, 2013, Valentine was named athletic director at Sacred Heart University in Fairfield, Connecticut. Valentine officially began his new career as athletic director on July 1, 2013.New Jersey Sports Writers Association "Sports Humanitarian of the Year" (2001)
Since 1980, Valentine has owned and operated Bobby Valentine's Sports Gallery Cafe, a sports bar that is located in his hometown of Stamford, with franchises slated to open in Norwalk, Connecticut, Arlington, Texas, and Middletown, Rhode Island.
In 2010, Valentine started the production company, Makuhari Media, with producing partner Andrew J. Muscato. The company produces sports themed documentaries.
In 2011, Mayor Michael Pavia named Valentine Director of Public Safety for the city of Stamford, Connecticut. Valentine was paid a token $10,000 salary for this position, which he pledged to donate to city charities. Valentine left the position 11 months later to manage the Red Sox.
In 2013, on the twelfth anniversary of the September 11 attacks, Valentine made comments that accused the New York Yankees of not contributing support to the New York community in the wake of the attacks. He was widely criticized for the inaccuracy of his comments, as many media sources documented several occasions on which the Yankees visited victims and workers after the attacks, and for the untimeliness of trying to take credit for helping. TBS had originally planned to feature Valentine as a studio analyst during its MLB on TBS coverage for the 2013 postseason, but reportedly declined to do so after the negative publicity his comments attracted.
Valentine is married to Mary Branca, the daughter of former Brooklyn Dodgers pitcher Ralph Branca, and together they have a son Bobby Jr. (born April 23, 1985).