It was implied that he wanted Jessie Prescott to grow up to join any type of army (navy, air force, etc.). He was the one taught Jessie a few moves to defend herself. Col. Prescott was not pleased when Jessie left to "fulfill her dreams" at New York.
In "G.I. Jessie", he sent a letter to Jessie telling her to come back home to Texas. At the military base in Texas, Col. Prescott was quite displeased that she brought the Ross kids along. He hated the fact that they were weak and caused havoc by driving the B.A.T.. Later, he reveals his secret reason for Jessie to return home; that he was going to marry Col. Shannon and go againest their families' feud. Jessie was not satisfied, because she is actually Darla's mom. Throughout most of the episode, he kept forcing her to get along with Darla and to keep the Ross kids from driving the B.A.T., which failed. During the rehearsal dinner, after Luke accidentally fired a rocket (thinking that the "R" meant reverse) at the wall, Col. Prescott knew that they crossed the line and scolded Jessie. This causes her to grieve, gave up on the Ross's lives, and refused to attend her father's wedding. At the wedding, after getting married, he saw that Jessie decided to attend the wedding anyway. He was last seen dancing with Jessie.