Before you start feeling too sorry for Roger Clemens over having failed in his last two attempts at winning 300 games after leaving the game with the Yankees leading, consider Early Wynn.
Wynn enetered the 1962 season with the White Sox needing 8 wins to get to 300. He had his last great season in 1959, going 22-10 with a 3.17 ERA. Coincidentally, so did the Chisox, who won the AL pennant for the first time since the 1919 "Black Sox" disaster and last time until 1983. These White Sox were slipping toward mediocrity and would finish 85-77 in 1962 in fifth place in a 10-team AL. Wynn had witnessed a similar slippage in his career. He won 13 games in 1960 but lost 12 and saw his ERA rise to 3.49 (still 9% better than the league average). In 1962, he sustained that level with a 3.51 ERA and 8-2 record, but he lasted 17 games or roughly half a season. If he had finished the season, he would have had the projected win total needed to reach 300 for his career.
When the 1962 season rolled around Wynn was 42 and the Sox were in the midst of a youth movement. A number of older stars were either taking on reduced roles or had left the club. That includes 1961 players like Sherm Lollar, Minnie Minoso, Roy Sievers, Billy Pierce, Cal McLish, Luis Aparicio, Al Smith, Turk Lown, Warren Hacker, Don Larsen, and Herb Score, who were all gone by 1963 (aside from 35 games by Lollar).
Wynn stood at 7-12 on September 8, with a 6-3 over the Senators at Comiskey. He had one win to go to reach 300. He had just lost two heartbreakers: 2-0 against the Twins' Jim Kaat on August 28 and 4-3 against the Indians' Pedro Ramos in the first game of a doubleheader, September 3. Win 299 broke a personal four-game losing streak (with a 2-3 loss to Jim Perry and a 9-2 to Robin Roberts preceding the two above).
Wynn had three starts remaining and lost each one miserably: 5-10 to Boston at home September 18, 1-5 to the Yankees at home September 23, and 3-7 to the Yankees away September 28. In the last game Wynn led 3-1 going into the seventh but allowed 6 over the next two innings.
In the offseason, the White Sox released him to pursue his 300th win elsewhere (talk about a great marketing department!). When other options did not present themselves, Wynn returned to the White Sox only to get cut in spring training.
He signed with his old team, the Indians, on May 31, 1963. His first start was June 21 against-who else?-the White Sox (apparently the Indians' did have a good marketing department). He hooked up in a pitchers' duel with Juan Pizzaro, with no runs scored through eight full innings. With two outs in the ninth and a man at third, Wynn allowed a game-winning home run to Ron Hansen.
His next start was June 28 again against the White Sox, this time at Comiskey. He and Chicago starter and future baseketball star Dave DeBusschere matched up for a 2-2 tie through five and one-half innings. Wynn fell behind 3-2 in the sixth. His spot in the order was due up third in the top of the seventh, and even though the first two batters were out, Wynn was pinch-hit for. The Indians ended up losing, 4-3.
His next start was Independence Day against the Red Sox at home in the first game of a doubleheader (again good marketing). He left after six innings with a 1-0 lead after allowing a lead-off single in the seventh (sound familiar?). The Indians ended up winning, 4-3 in 12 innings, on a Jerry Kindall home run, but Wynn was no longer the pitcher of record.
He next pitched two meaningless innings of relief, July 7, in the second game of a doubleheader against the Yankees at home. He entered the game behind, 4-2, and pitched two shutout innings. The Yankees ended up winning 7-4 in ten innings.
His next start was July 13 in the second game of a doubleheader against the Kansas City A's away (only 13,565 showed up). The Indians led 1-0 going into the bottom of the fourth when Wynn allowed a leadoff homer to George Alusik to tie the game.
He made up for it in the fifth, leading off with a single (the only man to do so in his 300th win), scoring a run, and starting a four-run rally. The Indians ended up scoring all their runs with two outs with four singles and two walks. The inning ended with catcher John Romano trying score on an Al Luplow single to left.
Wynn allowed three in the bottom of the fifth after the first three batters singled. The bases were loaded with one out for Jerry Lumpe. Lumpe doubled to right to drive in all three runners but Lumpe, representing the tying run, was out at third trying to stretch the hit to a triple. Wynn got Alusik to pop out, and the inning was over.
Wynn was up second in the top of the sixth and he was pitch-hit for by Woodie Held, who doubled but did not score. The Indians added two more runs to win 7-4. Jerry Walker pitched the final four innings, allowing just three hits and no runs for a posthumous save.
Wynn had his 300th and final win. He is only one of three men, Steve Carlton and Nolan Ryan being the others, to not complete his 300th game. He would start only one more game, July 27 again against KC, in which he lasted just four and one-third innings. In total he pitched 15 more games and just figured in one more decision, a loss July 21 at Yankee Stadium, in which he allowed one run in 2.1 innings. He ended up with a 2.28 ERA in 20 games.
So for a man who would be among the top 21 in wins all-time, the aptly named Early Wynn would only win one of his last 23 games and two of his last 28. He is said to have taken the most attempts (eight) to win his 300th game. It is also said that Roger Clemens has a picture of Wynn in his locker to remind him of who is ahead of him in career wins.
Maybe with the road Wynn traveled to get to 300, Clemens should find someone else to emulate.