After graduating from Humble High School in Humble, Texas, Boston became a three-year starter for the Ohio StateBuckeyes (1996–98). His 191 pass receptions as a Buckeye remain a team record, as do his career average of 5.2 receptions per game and 910 career punt return yards. His 2,855 receiving yards were a school record until surpassed by Michael Jenkins in 2003. With 36 career touchdown receptions (and one two-point conversion), Boston averaged 5.89 points per game.
Boston's best-remembered moment remains his game-winning five-yard touchdown reception from quarterbackJoe Germaine with 19 seconds remaining in the 1997 Rose Bowl. He is also remembered for being put on multiple highlight films after Marcus Ray knocked him out cold in the Michigan vs. Ohio State game
Boston left Ohio State with a year of eligibility remaining, and was drafted in the first round of the 1999 NFL Draft by the Arizona Cardinals. In 2001, Boston had 98 receptions for 1598 yards and eight touchdowns, starting in the Pro Bowl.
Boston signed a seven-year, $47 million contract ($12 million guaranteed) with the San Diego Chargers in 2003. That season he caught 70 passes for 880 yards and seven touchdowns, though coach Marty Schottenheimer suspended him for a game after he cursed out strength coach Dave Redding. Despite his sterling on-field performance, Chargers GM A.J. Smith traded Boston to the Miami Dolphins for a sixth round draft choice, citing his moody personality and lackadaisical practice habits.
Before the 2004 season, he tested positive for steroids and was ordered to serve a four-game suspension. The suspension became academic after he tore ligaments in his knee and was unable to play for the entire season. The Dolphins cut him at the end of the year, then proceeded to re-sign him for the veterans' minimum for 2005. He played in five games that year before tearing knee ligaments again.
After spending the 2007 season out of football, Boston signed with the Toronto Argonauts of the Canadian Football League on April 21, 2008. Boston reported to training camp but his medical report showed a stress fracture in his right foot and recommended surgery. He was placed on the suspended list, never practicing or playing in the pre-season. A second doctor's opinion, however, was that it was a two-year-old injury and cleared him to play in the regular season opener on June 27, 2008, when he recorded 2 receptions for a total of 16 yards. Following the game, however, Boston reported feeling too much pain and opted to follow the original doctor's suggestion of surgery requiring a 10 to 12 weeks rehabilitation period.
Boston's father, Byron, is an American football official in the NFL. He was not permitted to officiate regular season games in which David was playing. Byron worked as a line judge for one of his son's preseason games, between the Cardinals and the San Diego Chargers on August 14, 1999. David married his college girlfriend, Renee Dota and has 2 children with her. On August 23, 2007, Boston was arrested in Pinellas Park, Florida and charged with DUI after a failed sobriety test was conducted. Boston was released on his own recognizance. A video of Boston's field sobriety test was released through the local Tampa Bay media. The video depicts Boston asking to contact an attorney and being denied, and on several occasions asking to submit to breath and blood tests in lieu of the standard field tests. Boston's breath test resulted in a reading of 0.00 BAC. On September 10, 2007 it was released to the media that David Boston tested positive for GHB, a recreational drug with questionable ties to bodybuilding. After learning of the drug charges the Buccaneers quickly came to an injury settlement with Boston allowing him to be released. On September 12, 2007, Boston was officially released by Tampa Bay when they decided to sign Mark Jones. On December 1, 2011, Boston was accused of beating a woman after a night of drinking in Boca Raton. Boston allegedly punched the woman twice in the head, leaving a gash big enough to require 10 stitches after the incident in the 21000 block of Cromwell Circle, according to a Boca Raton police