While living in Corona, California, Strawberry attended Mater Dei High School in Santa Ana. During Strawberry's senior year at Mater Dei, he defended future NBA superstar LeBron James in a nationally televised matchup against St. Vincent–St. Mary High School of Akron, Ohio. Strawberry was lauded for his efforts, which included holding James to a 33% shooting performance and forcing him into seven turnovers. Considered a four-star recruit by 247Sports.com, Strawberry was listed as the No. 15 shooting guard and the No. 84 player in the nation in 2003.
College career
Strawberry assumed the role of a swingman for the Maryland Terrapins, and he was much valued for his on-the-ball defense. He averaged nearly 2 steals per game, leading his team in that category. He was also valued for his off-the-bench intensity; it is felt that Maryland's absence from the 2005 NCAA Tournament was due in no small part to a season-ending ACL injury Strawberry suffered in mid-January of that year. While he was primarily a swingman, a lack of depth pressed Strawberry into the role of point guard during his junior year. He had various degrees of success in this new role, leading the team in both assists and turnovers per game. Strawberry received Honorable Mention All-ACC Freshman honors. During his junior year, he received Honorable Mention All-ACC Defensive Team honors, becoming the eighth player in Maryland history to lead the team in both steals and assists. In his senior season, Strawberry was voted to second team All-ACC.
On December 18, 2007, it was announced he was assigned to the Albuquerque Thunderbirds of the NBA D-League. He was named Performer of the Week for the week ending January 6. Strawberry was recalled to the Suns in place of another rookie, Alando Tucker, on January 10, 2008.
2008–09 season
On August 25, 2008, he was traded to the Houston Rockets for Sean Singletary, but was waived on October 24. Six days later, he signed with the Italian club Fortitudo Bologna for the rest of the season. In April, 2009, he suffered a meniscus injury to his left knee, ending his season in Italy. He then returned to the United States for surgery, and in July, 2009 he began a 6-month program in Los Angeles.
2009–present
In January 2010, Strawberry joined the Reno Bighorns of the NBA D-League. In July 2010, Strawberry joined the Los Angeles Lakers for the 2010 NBA summer league. On September 17, 2010, he was signed by the New Orleans Hornets to a non-guaranteed one-year deal. However, he was later waived by the Hornets on October 20. Afterwards, Strawberry re-signed with the Reno Bighorns. On January 18, 2011, he signed with Lietuvos rytas of Lithuania until the end of the 2010–11 season. On August 26, 2011, Strawberry signed a two-year deal with the Israeli club Hapoel Migdal. After one season in which he averaged 15.6 points in the Israeli League, he parted ways with Hapoel on June 25, 2012. On September 20, 2012, Strawberry signed with the Croatian club Cibona. On June 22, 2013, Strawberry signed with the Capitanes de Arecibo of Puerto Rico for the 2013 BSN season. On July 12, 2013, he re-signed with Cibona. On December 25, 2013, he was released by Cibona due to financial problems of the club. Two days later, he signed with Pau-Lacq-Orthez of France for the rest of the season. On June 27, 2014, he signed with Piratas de Quebradillas of Puerto Rico for the 2014 BSN season. On July 2, 2014, he signed a one-year deal with Pınar Karşıyaka of the Turkish Basketball League. On July 2, 2015, he signed a two-year contract with the Greek club and EuroLeague powerhouse Olympiacos. After one season, he parted ways with Olympiacos. On July 22, 2016, Strawberry signed with Turkish club Beşiktaş for the 2016–17 season. On July 3, 2017, he re-signed with Beşiktaş for one more season. On July 29, 2018, Strawberry signed a one-year deal with Herbalife Gran Canaria of the Liga ACB and the EuroLeague. On October 31, 2019, he has signed with Orléans Loiret Basket of the French Pro A. In June 2020 he signed for one term at Liga ACB team UCAM Murcia.
