Complex sentence: Bragger set him on the road to stardom and Tommy won many races out of him, but when Bragger went for a spell, Tommy spent all of his winnings on flashy suits, hired cars and drinking.
Split into simpler sentences: Bragger set him on the road to stardom and Tommy won many races out of him. But, when Bragger went for a spell, Tommy spent all of his winnings on flashy suits, hired cars and drinking.