The Rider, Portrait of Entrepreneur John Rooney { 74 ” x 65” ]· Carbon pencil, blackening watercolours, and inks on paper mounted to canvas · [ 2019–2025 ]
The mask of freedom found through motion and trust.
This portrait captures John Rooney as a modern polo rider—poised on horseback, reins tight in hand, gaze steady and the ball. The horse is powerful yet calm, muscles taut beneath a coat that gleams in faint light, while the background dissolves into blackening drips that blur sky and ground into a single shadowed horizon. The rider sits tall, not in armor but playing polo in the quiet confidence of someone who has ridden through storms and emerged unchanged.
The blackening layers rise from the horse’s hooves and the rider’s boots, spreading upward like dust kicked up by the journey—symbolizing the accumulated weight of decisions, risks, and relentless forward motion. The rider’s face is unmasked: eyes clear, jaw set, the lines of experience etched without apology. He rides not to escape but to arrive, carrying the knowledge that every mile costs something and every choice leaves a mark.
The work celebrates the entrepreneur as a polo player: the one who sees the path, takes the reins, and keeps moving through uncertainty. Yet in the deepest blackening, a faint gleam catches on the horse’s bridle and the rider’s hand—the quiet reminder that even in motion, there is stillness, purpose, and the possibility of arrival.
A meditation on drive, resilience, the cost of leadership, and the enduring optimism that persists when one keeps riding toward what matters—dark yet eternally hopeful in its refusal to dismount.
Studio view, or related works: blairaiken@raincage.com
Inspiration & Personal Connection
This painting draws inspiration from George Stubbs’ iconic *Whistlejacket* (1762), the powerful, monumental portrait of a horse captured in full motion — raw, proud, and untamed.
In my version, the rider and horse become a single expression of freedom and unmasking. Horses have always brought me a profound sense of honesty — in the saddle, masks fall away. There is no pretending, no performance; only the immediate truth of balance, trust, and shared movement. I felt this deeply while watching John play polo — the intense focus, the rhythm between rider and horse, the exhilarating freedom that emerges in those fleeting, teaming moments when human and animal move as one.
The blackening layers trace the tension between control and surrender, the discipline required to ride well, and the liberating release that comes when we let go of our constructed selves. Through this work, I explore how horses strip us down to something more essential — revealing both our vulnerability and our capacity for grace.
Yet even in this moment of powerful motion, a faint gleam persists — a quiet reminder that true freedom is often found not in dominance, but in partnership, trust, and the willingness to be unmasked.
Dark yet hopeful.
Studio view, or related works: blairaiken@raincage.com
Dark yet hopeful.
George Stubbs, Whistlejacket, 1762