I used to call myself "the milestone jinx".
Why? Because for years I kept missing major baseball milestones by one. The first one was Ernie Banks' 499th career HR on May 9, 1970. Had the actual home run Ernie hit in Montreal on June 30, 1969 been correctly ruled a home run instead of having the umpire believe Expos OF Rusty Staub, who said on a rainy, murky night that the ball had gone under the fence and given Ernie a double, the May 9, 1970 homer would have been Ernie's 500th, in front of a nearly packed house on a sunny Saturday. Instead he hit it in front of about 5,000 people on a cold and gloomy Tuesday afternoon.
Then I was in St. Louis to see the Cubs one day before Lou Brock got his 3000th hit off Dennis Lamp.
And I was in Milwaukee on September 8, 1992, specifically hoping to see Robin Yount's 3000th hit. He needed two. He got one and walked in the bottom of the eighth, his last at-bat of the day. The crowd booed.
So on September 16, 1993, when I was traveling and changing planes in Minneapolis, I could have switched my flight back to Chicago and gone to try to see Dave Winfield get his 3000th hit. But he needed two. "No way", I thought, remembering the previous year. So I stayed on my original flight and didn't go to the game. Well, he got it -- in the ninth inning, and scored the tying run.
I was happy to not see Roger Clemens get his 300th win, because it meant the Cubs beat him at Wrigley Field in one of the most memorable games of the 2003 season.
I had planned for a couple months to go to San Francisco in 2004 to see the Cubs play... and that's when I finally got one, Greg Maddux's 300th win against the Giants on August 7, 2004, after witnessing him leaving his previous start at Wrigley six days earlier trailing 2-1; the Cubs rallied to win, but the victory went to Kent Mercker. Incidentally, the first Cub to relieve Maddux in that game was Ryan Dempster; that was Dempster's first appearance in a Cub uniform.
Since then, I have witnessed one more -- Tom Glavine's 300th win against the Cubs on August 5, 2007, a game I'd rather the Cubs had won, and also notable for the serious hamstring injury Alfonso Soriano suffered running the bases. It wasn't until Soriano came back three weeks later that the Cubs made their run to the 2007 NL Central title.
This is a rather long way of introducing Dan Schlossberg's new book, "The 300 Club", the story of all of the 300-game winners, which also asks the question, "Will there be any more?"
Schlossberg profiles each of the 300-game winners and managed to contact personally all of the living ones; there are in-depth interviews with all of the latter. If you don't think that the pressure of reaching a milestone like this affects a veteran major league pitcher, consider these quotes from Greg Maddux:
Greg Maddux remembered the burden of #300 and what it did to his wife Kathy, who was in charge of ticket arrangements and travel for a myriad of family and friends. "I didn't want it to drag on," Maddux remembered, who got #300 while pitching for the Cubs in San Francisco on August 7, 2004. He got it on his second try. "I had put my wife through another five days of hotel arrangements, tickets and 15 calls from everybody who wanted to come. That's the kind of inconvenience it puts on your family when you go through something like that. I know it's a big deal and I was thrilled to accomplish it but it puts a lot of added burdens on the people around you."
And from Tom Seaver:
Tom Seaver won #300 at Yankee Stadium while pitching for the White Sox on August 4, 1985, beating the Yanks 4-1 on a 6-hitter. Seaver pitched for the Sox in 1984-85 and part of 1986. He won #300 on Phil Rizzuto Day at Yankee Stadium. "It meant more to me than I was willing to admit. It was a constant emotional drain. The last time I'd felt like that when when I had a perfect game going against the Cubs in 1969. It was nice to win my 300th game in New York, in front of some fairly sophisticated fans." He was not surprised to see so many in the stands that day rooting for the Sox, and not the Yankees. "I wasn't totally surprised about that. Mets fans could buy tickets, too. Some people are Mets fans, some people are Yankees fans, and some people are baseball fans. I had made my name in New York so people came out to see me pitch there."
The book's author doesn't think there will be any more 300-game winners:
"I know I said nobody will get to the 300 win level again...and I still feel that way. But if ANYBODY can get there, it would be Roy Halladay. He pitches well into the 8th and 9th innings of games, which gives him a chance to pick up extra wins. He also can throw up to 130 pitches a game, so he has endurance. I know he is 33, and has 155 wins, but he is a horse and I think he can pitch to age 41. If he does that he has an outside chance, especially if he stays with a team that wins games like the Phillies. But again, it is an outside chance. I just think we've seen the last of 300 game winners.
"Think about it this way: you gotta win 15 games a year for 20 years or 20 wins a year for 15 years. With today's salaries, there's not a whole lot of guys who will want to do what it takes to hang around that length of time. They have all the money they need at an earlier age and are set up for life."
This is exactly what was said in the early 1970's. At the time, only two pitchers -- Warren Spahn in 1961 and Early Wynn in 1963, and Wynn just barely -- had reached the 300 level since Lefty Grove in 1941. Around that time, Bill James wrote an article predicting there would be a "flood" of 300-game winners coming up -- and that's exactly what happened. Ten pitchers have been added to the 300-win club since then.
James recently changed his tune; Tom Tango quotes James in this link:
It recently occurred to me, though, that one can track this change in a different and perhaps better way by looking at the data for just one season. In 1884, seven major league pitchers won a total of 329 games—59 by Old Hoss Radbourn, 52 by Guy Hecker, 48 by Charlie Buffinton, 46 by Pud Galvin, 43 by Billy Taylor, 41 by Charlie Sweeney, and 40 by either Jim McCormick or Bill Sweeney. Eight pitchers won 40 or more games. If seven pitchers can win 300 games in a season, then, how long would it take a top-flight pitcher to win 300 games? Seven years. You just have to remain one of those top seven pitchers for seven years. ...
We started the decade back at 16, then stabilized at 18 (18, 18, 18), and then this year  it took 19 pitchers to add together to get a total of 300 wins. 19 is a high number. 19 is the highest number ever, except for the strike-shortened seasons and the years 1876-1878. 19 is close to 21, and at 21, 300 game winners are gone. ...
Pitchers don’t have to come out of the game at the 100-pitch mark; it’s just a choice that managers make. If the commissioner succeeds in speeding up the games, one result of that should be more complete games, which would drive this number down, thus making it easier to win 300 games. All I will really say is that it is still possible to win 300 games now. Ten years from now, if that number is 21, 22, 22, 22. . ..it’s over.
It's hard to say. James may very well be correct, given the way pitchers are used these days. I don't believe that it's a financial issue, as Schlossberg says; look at Jamie Moyer, who does want to pitch till he's 50 and appears this year to be pitching at a competitive level. If Moyer winds up this year with 270 wins -- not an unrealistic goal -- he could do it. Roy Halladay, mentioned above, should end this season at age 33 with about 165 wins. He'd have to pitch into his early 40's; so would Andy Pettitte. Maybe they wouldn't need the money -- but competitive professional athletes, when seeking a goal, would probably do it for the accomplishment, as long as they feel they can still pitch and teams would still want them.
The pitcher not mentioned by Schlossberg who has a real shot at 300 is CC Sabathia. Sabathia won't turn 30 until next month and should end this season with over 150 wins (he's currently at 141). As long as he can stay healthy and has a desire to pitch, he's got a real shot at it.
A longer shot is Carlos Zambrano, who just turned 29. Returning to the rotation tonight with 106 career wins, if Z can return to the form which had him not miss a start from 2003-2007 and pitch as he is capable of pitching, maybe that 300th win could await him 12-13 years from now.
The book is informative and food for thought, although there were some annoying typos and the 300th win boxscore under the Don Sutton chapter was Warren Spahn's 300th win. This one's definitely worth your time. Full disclosure: the publisher sent me a review copy of this book.