Bart was pranking Mrs. Krabappel by answering her personals ad and carrying out a chain of correspondence with her, using "Woodrow" as an alias. When Mrs. Krabappel proposed that they exchange pictures and enclosed a sexy photo of herself, Bart at first had no idea what to send her in return. However, he started flipping through a book of NHL stars, came across Howe's picture, and decided to use it for Woodrow's picture. As Bart cut Howe's photo from the book, he said, "Strap on your skates, Gordie, you're goin' in."

Mrs. Krabappel was pleased with the photo. She framed it and kept it on her desk at school.

Gordie Howe (born March 31, 1928) is generally regarded as one of the greatest ice Hockey players of all time. He enjoyed a very long professional career, even playing several seasons on teams with two of his grown sons.
Howe's career statistics are shown over his picture at the beginning of the episode's closing credits.
The Simpsons writers originally wanted to have Bart send Mrs. Krabappel a picture of American football player Johnny Unitas, but they were unable to obtain the rights to use Unitas's image for free.