Some artists speak through their brushes more than their words — and Max Winningham is a perfect example of that quiet brilliance. Hope first met Max in 2019 at a class with Steve Ross and Dana Jester in Winchester, Indiana. From that very first workshop, a painting friendship was born. Now, each return trip to Winchester feels like catching up with an old friend — one whose signature “Max Tree” has become a beloved inside joke among fellow painters.
Max’s talent stretches far beyond classic landscapes. While rooted in the Bob Ross tradition, his work often ventures into new creative territory — especially when painting alongside his cousin Dana. Together they’ve tackled ducks, fish, tigers, and more, and Max always finds a way to infuse each piece with his own perspective and unique detail. His seascapes, in particular, carry an emotional depth and atmosphere that set them apart. (Hope still wonders how she doesn’t own one yet.)
He may be soft-spoken and reserved when you first meet him — usually tucked toward the back of the classroom, quietly focused — but give it time. Once you’re in Max’s circle, you’ll find yourself part of something bigger: a deeply supportive community that feels a lot like family.
