President Trump’s high confidence in winning Texas is vexing some Republican insiders, who fret that his 2020 campaign is unprepared to handle a generational challenge from the Democratic Party for control of the state’s critical 38 votes in the Electoral College.

The Democrats flipped two suburban Texas congressional districts and another dozen seats in the state house in the midterm elections, while Democrat Beto O’Rourke nearly ousted Republican Sen. Ted Cruz. GOP strategists with deep experience in Texas are bracing for the possibility of more turbulence next year, with some worrying that Trump’s top political officials in the state are ill-equipped for the competition. Others are pleased with the campaign’s Texas leadership, but question party strategy.