Wynn, however, had picked up his 299th victory before the end of 1962, and he was determined to get to 300 career wins. He attended spring training with the White Sox in 1963 but failed to make the team. Several teams offered him one-game contracts, but Wynn held out for a full-time deal, which he got from the Indians on June 21. Cleveland then added him to the starting rotation to give him the opportunities he needed. He failed to win in his first three starts with the Indians that year, and the nine months and seven starts that had elapsed from 1962 to 1963 are still, as of , the longest gap between any pitcher's 299th and 300th wins in MLB history.
