Dick’s Roof Repair Awards 2025 Free Roof to Bob and Alisha Sheriff

Dick’s Roof Repair Continues Tradition of Giving Back with 2025 Free Roof Award

Since 1957, Dick’s Roof Repair has been a trusted name in roofing throughout Southeast Wisconsin. In 2020, the company began a new tradition: giving away a free roof each year to a deserving member of the community. What started as a gesture of gratitude has grown into a beloved annual event that uplifts local heroes and neighbors.

In its first year, the program recognized the extraordinary efforts of healthcare workers during the height of the pandemic. In 2021, a local firefighter received the honor. The following year, two roofs were awarded to dedicated educators. In 2023, a longtime volunteer was selected. Last year, a veteran was chosen for their selfless service.

Now, in 2025, the tradition continues with a powerful story of sacrifice, resilience, and community spirit. This year’s recipients, Bob and Alisha Sheriff, were nominated by neighbors who praised their commitment to both country and community.

Bob and Alisha have each served in the U.S. Army for over a decade, with 19 years of service for Bob and 14 years for Alisha, including multiple deployments to Iraq and Afghanistan. Recently, the couple purchased their first home as they transitioned into civilian life and began raising their three young children.

Shortly after moving in, a hard rain revealed a leaking roof. Repair quotes were far beyond what the family could afford, leaving them to face worsening damage as the weather continued. Nominations poured in from neighbors and community members who described Bob and Alisha as selfless, kind, and always giving back. The couple has worked with local nonprofits to deliver food, toys, and essential supplies to families in need.

“At Dick’s Roof Repair, we believe in honoring the people who make our community strong,” said Jeff Milkie, President of Dick’s Roof Repair. “Bob and Alisha embody service, generosity, and resilience. After dedicating so much of their lives to serving our country and helping others here at home, it is our privilege to ensure their family has a safe and reliable roof over their heads.”

From newlyweds balancing military life and parenthood to dedicated neighbors committed to serving others, Bob and Alisha Sheriff exemplify what it means to be good neighbors. Dick’s Roof Repair is proud to provide them with a new roof as part of its annual tradition of giving back.

For the Sheriffs, this new roof is more than just a home improvement. It is a symbol of gratitude from a community they’ve given so much to.