Damondtaye J. Gaines

Damondtaye James Gaines, age 33, was born in Detroit, Michigan to Tamika Gaines and Omar Cobb. Damondtaye's journey came to a sudden close on October 30, 2025, in Rochelle, Illinois, leaving a sense of loss that will echo in the hearts of his family and friends.

He was blessed to have two families: one in Detroit, MI and the other in Brookston, MN. Damondtaye spent his younger years in Detroit until moving in with his grandmother, Mattie Collins, who he adored and respected. He then moved to Brookston, MN in 2006 to reside with Donald “Bruddy” and Maeve Olesiak. He attended AlBrook High School where he enjoyed and excelled at basketball and football before graduating in 2010.

Driven by the thrill of the open road and a steadfast determination, Damondtaye fulfilled a lifelong dream of obtaining his Commercial Driver’s License (CDL) to work as an over-the-road truck driver. This career allowed him the freedom to travel and explore, weaving through the vast landscapes of America, all while showcasing his commitment to hard work. Every mile traveled was a testament to his dedication, embodying the spirit of adventure that defined his life.

He is preceded in death by his grandmothers, Mattie Collins and Janet Gaines. He is survived and missed by his parents, Tamika Gaines and Omar Cobb; second parents his Ma and Dad, Donald “Bruddy” and Maeve Olesiak; his partner, Kadi Felver and their son, Zayne; mother of his children, Maria Rojas and their children, Sincere and Knowledge; his friend who became like a brother to him, Aaron Olson; best friend, Liz Boustead; foster brother, Chris “Ner-Ner”; and countless other foster brothers, aunts, uncles, cousins, and friends.

Damondtaye’s memory will forever resonate in the stories shared, the laughter remembered, and the lives he touched.

A celebration of Damondtaye’s life will be held on November 22, 2025 beginning at 4:30 PM at the Country Corner Saloon and Grill, 9497 Hwy 2, Brookston, MN, 55711. In lieu of flowers, if you would like to support Damondtaye’s three children, you can venmo @Maeve-Olesiak…please add a note to the donation “D’s Children”