An acolyte of Siegbert Tarrasch, his sound, strategic play enabled him to defeat a number of the world's top players, including David Bronstein, Aron Nimzowitsch and Milan Vidmar.

However, his health and tactical play were insufficiently strong to enable him to repeat these victories on a consistent basis.

Winter was a widely respected author of chess books and was a nephew of J. M. Barrie, the creator of Peter Pan.

Harry Golombek described his play as "classic, scientific and sober; away from the board, he was revolutionary, illogically moved by his emotions (he contrived to be both a fervent communist and a staunch patriot) and, more often than not, drunk."

Winter has the distinction of being the only British Champion to have served time in prison (for his political activities).