On November 18, 2025, our hearts were forever changed as we said goodbye to James Richard Bailey Jr. - a devoted father, husband, song, brother, grandfather, and friend whose presence meant more than he ever realized.

Born on October 13, 1964, in Baltimore MD, to the late James Richard Sr. and Judith Pearl, James affectionally known to family and friends as "Woodie"—carried from the start a spirit entirely his own. Quiet, steady, and observant, he moved through life with a calm exterior that often hid a sharp wit and a playful sense of humor. Sarcasm was his signature, and his one-liners were more than jokes—they were his way of connecting, comforting, and expressing love.

James was honest in a way few people dare to be. He had no cut cards for anyone; you always knew exactly where you stood with him. That honesty, paired with unwavering reliability, made him someone others naturally leaned on, He never asked for much, yet he gave more than most.

James was the true definition of an introvert. He could walk into a room full of people, give a quick head nod, and disappear into his own space. Growing up, he enjoyed spending time with his friends and developed a deep love for pigeons, which he raised for several years.

He loved his family with a depth that didn't always require words. Though a man of few words, his devotion— especially to his mother—was unmistakable. His children were his pride, and his grandchildren were the brightest lights of his life. Nothing filled him with more joy than seeing "Lil Ice," the nickname he lovingly gave his grandson Artist. James found peace in life's simplest joys—watching his favorite Westerns, taking long, adventurous walks with his dog Teddy B, and sharing vacations and quiet moments with his wife, Belinda, who was his anchor.

In his final months, Belinda cared for James with extraordinary devotion. She listened, comforted, and support: him through every need, standing by him with strength, patience, and compassion. Her love gave him peace, safety, and understanding in ways words cannot describe.

To be loved by James was to be seen, protected, and understood—without ever needing to explain a thing.

James is survived by his four children—Jamal, Mariah, Jason, and Justin—who carry his strength and resilience within them; his stepson Diontay, with wham he shared a meaningful bond; and his beloved grandchildren: Jahli. Jackson, Artist ("Lil Ice"), Xavier ("Lil Bun"), and Leilani ( "Sweet Pea")—each a source of joy, laughter, and purpose. They will grow up hearing stories about the man who adored them.

He is also survived by his loving mother Judith Pearl; his sisters Tamara Bailey, Adrienne Bailey-Hill, and Monefia Clark; his brother Kelly Bailey; and two cousins dear to his heart, Kimberly and Bianca; along with a host of nieces, nephews, family, and friends who hold cherished memories of him.

James is preceded in death by his father, James R. Bailey Sr, and his brother, Mark A. Bailey, whom he loved deeply and now joins in peaceful rest.

Though the world feels emptier without him, the love he gave continues to live—in every memory, every laugh he left behind, and every life he touched. James will be missed beyond measure, but remembered forever—quietly, powerfully, and with deep, unwavering love.