For 34 years, Bill O’Leary was involved as a coach and a teacher. 

All comes full circle on September 26 at the Homecoming parade as O’Leary, named this year’s Grand Marshall–leads the Craig’s clubs and sports through the neighborhood

The parade starts at 2.

When O’Leary heard that Mr. Phillips selected him, he was surprised. 

Phillips told him that there was “no one more capable” to serve as Grand Marshall.

O’Leary still feels invested in Craig, as shown by his long term involvement in the school, and being honored as Grand Marshall brings back memories of the 34 years that he dedicated to Craig.

O’Leary said, “This is a great honor and I am very excited to lead all of the various clubs and sports of Craig.” 

  Born and raised in Milton, Wisconsin, O’Leary attended the University of Wisconsin-Whitewater, graduating in 1974 with a degree in special education. 

He taught special-ed and coached wrestling and football. 

He worked to integrate the special education students into Craig and the community and fiercely advocated for them. 

“I wanted to make the kids and school know that the special-ed kids are an equal part of the school,” he said.

By making the special-ed students walk around the school, say hi to everyone and give high fives, he brought the familiarity of them to other students.

Coach O’Leary hopes that by being Grand Marshall, he can continue the excitement that he experienced in his time at Craig. 

 As a coach, however, Homecoming week was a nervous time.

“I was concerned that the players might be distracted by all the activities of the week, but I still wanted them to have fun,” he said. 

As Grand Marshall, he hopes the students have a fun and memorable week.

“Homecoming Week is a huge part of football and student life,” he said. “And everything was better if we won the football game.”