In 1992, Raymond was elected to the House from District 44, when he was residing in Benavides. He left the House temporarily after three terms. In 1998, he instead challenged the Republicannominee for Commissioner of the General Land Office, David Dewhurst of Houston. In the general election, Dewhurst easily prevailed for the right to succeed Democratic Land Commissioner Garry Mauro of Bryan, who instead ran for governor of Texas that year against George W. Bush. On the day of the inauguration of George W. Bush as U.S. President, Raymond won a special election in Webb County to succeed Henry R. Cuellar in the state House of Representatives. Cuellar had stepped down and briefly served as Texas Secretary of State under the new governor, Rick Perry. Raymond defeated a multi-candidate field of Democrats, including Carlos Ygnacio "C.Y." Benavides, III, a Laredo-area businessman, who thereafter in 2006 ran unsuccessfully for Webb County judge against Danny Valdez. In 2006, Raymond fell.07 percent plus one vote short of an outright victory in the Democratic primary. He finished first with 11,806 votes ; his chief opponent Mercurio Martinez, a former county judge of Webb County, trailed with 7,650. Two other contenders held the remaining 17.9 percent of the vote. In the runoff in April 2006, Raymond prevailed, 8,828 votes to Martinez's 6,456. Raymond is considered a strongly partisan Democrat. He filed the lawsuit opposing the 2003 congressional redistricting plan adopted by the states' Republican majority. In 2006, the United States Supreme Court, with the Ronald W. Reagan appointee JusticeAnthony Kennedy providing the swing vote, ordered changes in the plan which proved favorable to Texas Democrats in the mid-term elections. In 2007, Raymond participated unsuccessfully in a coup attempt against Speaker of the Texas House of RepresentativesTom Craddick, a Midland Republican. During the opening session of 2007, Raymond was the only member who rose to ask fellow members to vote against Craddick, even though Craddick had no opponent. The refrain "Prove Me Wrong, Mr. Speaker," used by Raymond during this critical speech, was then repeated during the rest of the session, as opposition continued to build against Craddick. Twenty-six other members joined Raymond in voting against Craddick, but by the end of the session, a majority agreed with Raymond. At the beginning of the 2009 Session, Raymond and others finally succeeded in toppling Craddick by maneuvering the election of Representative Joe Straus, a Moderate Republican from San Antonio, as the still-serving Speaker of the House. In February 2009, Speaker Straus named Raymond vice-chairman of the House Appropriations Committee, making him one of the most influential Democrats in the chamber. Raymond was also named a member of the House Committee on Border Affairs and Intergovernmental Relations. In 2013, Raymond voted against House-passed legislation which would prohibit abortions in Texas past twenty weeks of gestation, require physicians performing abortions to have admitting privileges at local hospitals, require that the abortions be performed in surgical centers, and require monitoring of abortions. Opponents of the measure claimed it would shut down abortion clinics throughout Texas and place an "undue burden" on women seeking to end their pregnancy. In 2015, Raymond announced that he would re-introduce a bill with a companion state constitutional amendment to permit voter enactment at the local level of eight-liner slot machines. Current policy permits establishments with eight-liners to offer only prizes of no greater than $5 to the winners of the games. His measure would enable the state to regulate such games. A Laredo city council member, Charlie San Miguel, said he does not oppose Raymond's measure but fears an expansion of gambling "leads to addiction in some cases, leaving unable to provide for their needs..." San Miguel said Raymond's bill should also provide a "support network" for those inclined toward abuse of gambling. In the general election held on November 6, 2018, Raymond handily defeated his Republican challenger, Luis De La Garza, 25,383 votes to 8.775 votes.
