He is most known for his second place in the inaugural 1891 Bordeaux-Paris, that was won by his countryman George Pilkington Mills and for several attempts in the early 1900s to cross the English Channel swimming.

A good example of the dominance of British cycling in those days was the 1891 Bordeaux-Paris, which saw the Brits take the first four places, Holbein ranking second.

On 1 August 1902, Holbein failed again due to a tidal flow, heavy seas and a strong head wind, again 4 miles (6.4 km) from Ramsgate.

The mask was composed of American sticker's plaster with glass let in to enable him to see, and effectually preserve his eyes from injury.

During his attempt, he ate beef essence in liquid form and sandwiches, but was eventually pulled out when he could not make any headway against the tides.