Visiting Cuba in 1895, during its war of independence from Spain, he travelled unperturbed through some of the island's most dangerous territory while writing for the Daily Graphic.
The next year his regiment was transferred to India, where he fought Pushtun tribesmen on the border with Afghanistan, penning articles for the Daily Telegraph from a blood-splattered foxhole on the battlefield.
He was then sent to Sudan, where he took part in the British army's last great cavalry charge, at the Battle of Omdurman in 1898.
After narrowly losing a by-election in Oldham, he returned to the journalistic fray as a war correspondent in South Africa for the Morning Post during the second Boer war of 1899-1902.
There he hit the front pages in his own right; he was captured by the Boers while accompanying a scouting expedition on an armoured train.
Even that could not stop Churchill, who soon escaped from the prisoner-of-war camp, travelling almost 300 miles to safety in Portuguese East Africa.
As Mr Read notes, by the time of his return from Africa, Churchill had saved more than 4,000 from his writing, equivalent to 400,000 today.
With judicious economy, he told his brother, I shall hope to make that carry me through the lean years.
But he returned to old habits in the years to come.
Notable extravagances involved losing badly gambling in Monte Carlo and betting that share prices would continue to rise when the Wall Street crash hit.
Churchill did not continue to write simply for adventure or fun;
he did so to make ends meet.
But even that was not enough.
He required bail-outs from wealthy friends in 1938, 1940 and 1946 to save him from bankruptcy.
Both books manage to tell their tales of Churchill the adventurer and gambler elegantly.
And for a financial biography, Mr Lough's is a surprising page-turner.
But the two authors only briefly link their assessments of Churchill's personality to the important decisions he made in office—and even then only in vague terms.
For instance, both fail to mention how his frequent bouts of depression may have contributed to his impulsiveness and risk-taking.
Although their stories are worth telling, they have left bigger questions about Churchill to other historians.