14. Most Career Wins in MLB History (511)
Set By: Cy Young
MLB players make a ton of money. Like, a ridiculous amount of money. If you're a pitcher who wins a lot of games, you're rich as hell. When you hit 35 years old and have been in the league for 10 to 15 years, you have enough money for about four or five generations of your family, plus a few of their friends. So why would you stick around to play 25 or 26 years? That's basically what it would take to best Cy Young's record, keeping in mind that you'd have to average 20 wins a year to do it. Seeing as only two or three guys top 20 every season, the odds probably aren't in your favor.