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Simpson was elected mayor of Baker in 1992 over the Democrat Frank C. Blackburn. In the primary, he led with 1,997 (32.4 percent) to 1,147 (31.1 percent). Two other Democratic candidates held the remaining nearly 37 percent of the vote.<ref>Louisiana Secretary of State, Election Returns,  March 10, 1992.</ref> In the general election, Simpson defeated Blackburn, 2,100 (54.4 percent) to 1,762 (45.6 percent).<ref>Louisiana Secretary of State, Election Returns, April 11, 1992.</ref> In 1996, Simpson defeated a fellow Republican, Lamon L. Moody, Jr., 2,022 (82.6 percent) to 425 (17.4 percent).<ref>Louisiana Secretary of State, Election Returns, March 12, 1996.</ref> Simpson was unopposed for a third term as mayor in March 2000, but he served less than a year thereafter upon winning election as East Baton Rouge Mayor-President. In the seeking the greater position, Simpson claimed that he had saved the city of Baker millions through careful budgeting and financial management.<ref name=bio/>​

Simpson was elected mayor of Baker in 1992 over the Democrat Frank C. Blackburn. In the primary, he led with 1,997 (32.4 percent) to 1,147 (31.1 percent). Two other Democratic candidates held the remaining nearly 37 percent of the vote.<ref>Louisiana Secretary of State, Election Returns,  March 10, 1992.</ref> In the general election, Simpson defeated Blackburn, 2,100 (54.4 percent) to 1,762 (45.6 percent).<ref>Louisiana Secretary of State, Election Returns, April 11, 1992.</ref> In 1996, Simpson defeated a fellow Republican, Lamon L. Moody, Jr., 2,022 (82.6 percent) to 425 (17.4 percent).<ref>Louisiana Secretary of State, Election Returns, March 12, 1996.</ref> Simpson was unopposed for a third term as mayor in March 2000, but he served less than a year thereafter upon winning election as East Baton Rouge Mayor-President. In the seeking the greater position, Simpson claimed that he had saved the city of Baker millions through careful budgeting and financial management.<ref name=bio/>​

Six candidates, four Republicans and two Democrats, contested the October 2000 primary for Mayor-President. Democrat Holden led with 34,780 votes  (31.2 percent), and Simpson trailed with 27,928 (25.1 percent). Republican Rolfe H. McCollister finished third with 21,850 votes (19.6 percent). Three other candidates held the remaining 24 percent. One of those unsuccessful candidates was Republican Fred Columbus Dent, Jr. (1937–2010), a former [[United States Army]] Green Beret and the son of  [[Lucille May Grace]], a Democrat who served for multiple terms as the Louisiana Register of State Lands, no longer an elected statewide position. Fred Dent, Jr., drew 6 percent of the vote.<ref>Louisiana Secretary of State, Election Returns, October 7, 2000. Simpson then defeated Holden in the November 7 general election with 93,952 (56.9 percent) to 71,087 (43.1 percent). Simpson outpolled Republican [[U.S. President|presidential]] nominee [[George W. Bush]] in East Baton Rouge Parish, who received 89,128 votes (52.7 percent).<ref>Louisiana Secretary of State, Election Returns, November 7, 2000.</ref>​

Six candidates, four Republicans and two Democrats, contested the October 2000 primary for Mayor-President. Democrat Holden led with 34,780 votes  (31.2 percent), and Simpson trailed with 27,928 (25.1 percent). Republican Rolfe H. McCollister finished third with 21,850 votes (19.6 percent). Three other candidates held the remaining 24 percent. One of those unsuccessful candidates was Republican Fred Columbus Dent, Jr. (1937–2010), a former [[United States Army]] Green Beret and the son of  [[Lucille May Grace]], a Democrat who served for multiple terms as the Louisiana Register of State Lands, no longer an elected statewide position. Fred Dent, Jr., drew 6 percent of the vote.<ref>Louisiana Secretary of State, Election Returns, October 7, 2000.</ref> Simpson then defeated Holden in the November 7 general election with 93,952 (56.9 percent) to 71,087 (43.1 percent). Simpson outpolled Republican [[U.S. President|presidential]] nominee [[George W. Bush]] in East Baton Rouge Parish, who received 89,128 votes (52.7 percent).<ref>Louisiana Secretary of State, Election Returns, November 7, 2000.</ref>​

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Mayor Simpson was elected in 2002 as president of the Louisiana Municipal Association, having succeeded Edward Gordon "Ned" Randolph, Jr. (1942-2016) of [[Alexandria, Louisiana|Alexandria]] in Rapides Parish.<ref>{{cite web|url=http://www.laota.com/NewsletterWinter2002.htm|title=LATA Newsletter|publisher=laota.com|accessdate=November 20, 2009}}</ref> He was also president of the Louisiana Conference of Mayors. Early in 2004, he unveiled a 10-year plan endorsed by the U.S. Conference of Mayors with the goal of ending chronic [[homelessness]] in Baton Rouge. Simpson endorsed the Samaritan Initiative, an effort to tap into community-wide resources to move the homeless from the streets and temporary shelters into houses.<ref>{{cite web|url= http://www.ich.gov/library/simpson-testimony_07-13-04.pdf|title=Mayor President Bobby Simpson . . . On H.R. 4057|publisher=ich.gov|accessdate=November 30, 2009}}</ref>​

Mayor Simpson was elected in 2002 as president of the Louisiana Municipal Association, having succeeded Edward Gordon "Ned" Randolph, Jr. (1942-2016) of [[Alexandria, Louisiana|Alexandria]] in Rapides Parish.<ref>{{cite web|url=http://www.laota.com/NewsletterWinter2002.htm|title=LATA Newsletter|publisher=laota.com|accessdate=November 20, 2009}}</ref> He was also president of the Louisiana Conference of Mayors. Early in 2004, he unveiled a 10-year plan endorsed by the U.S. Conference of Mayors with the goal of ending chronic [[homelessness]] in Baton Rouge. Simpson endorsed the Samaritan Initiative, an effort to tap into community-wide resources to move the homeless from the streets and temporary shelters into houses.<ref>{{cite web|url= http://www.ich.gov/library/simpson-testimony_07-13-04.pdf|title=Mayor President Bobby Simpson . . . On H.R. 4057|publisher=ich.gov|accessdate=November 30, 2009}}</ref>​