Randall Winston was the Mayor of New York City throughout Spin City's six-year run. He was played by Barry Bostwick.

Mayor Winston was a city councilman for ten years prior to becoming Mayor and also a borough President for some time. He is a Democrat (this fact is mentioned only in passing, such as brief references to the DNC). He is a liberal and believes strongly in public education.

Winston appears to be an intelligent and charismatic mayor who has the ability to connect with voters. Much of this is a carefully orchestrated sham by his, especially Mike. The Mayor is actually unbalanced in a number of ways. He is childish, vain, outrageously dim and often oblivious to events, such as forgetting he is the mayor. He behaves in very odd ways behind the scenes, and sometimes in front of them. He has little or no self-control, blurts things out and generally behaves like a child. He is not, however, without a degree of media skill - he is capable of thinking on his feet and 'winging it' at public events when required. The Mayor also suffers from a lack of focus, letting his mind wander from topic to topic almost at random, and often becoming obsessive and carried away with minor, trivial things.