As for Winston, he existed, and presumably continued to exist. No arguing that.
The Rocky Franchise Mirrors Sylvester Stallone's Entire Career
Others have remarked before that Rocky can be seen as autobiographical. It's the story of a low-life street bum who boxes in his spare time until he takes a gamble at greatness and almost achieves it. While Sylvester Stallone was writing the script, he was being thrown out of cheap apartments for falling through on the rent, and he even took a role in a softcore porno for $200.
"Eh, still less embarrassing than starring in Rhinestone."
When Sly realized he had a winner with Rocky, he took a gamble, refusing to sell it at any price unless he could play the lead, and almost achieved greatness -- Rocky swept a bunch of Academy Awards, but none for Stallone himself. In fact, the full seven-film Rocky series mirrors Stallone's career, if you switch out punching for acting. Consider this:
In Rocky II, Rocky has little interest in boxing again, and goes right back to failing at everything. When his former opponent, Apollo Creed, calls their previous fight a fluke, Rocky finally agrees to get back in the ring to prove he wasn't a one-hit wonder.
"One-hit wonder. Get it? Get it?"
"I got it."