I'm pretty sure it does mean she overcame the obstacle of being a woman but he meant it in an admirable way, not a demeaning way. The entire world is still an Old Boys Club and the fact that Janet was the first just proves that there were barriers in place and she broke through those barriers. Still to this day, women are held back from advancing as a lot more than firemen, police officers, and combat soldiers. Even if laws have been changed, mindsets have not. The Old Boys Club is very very much alive and well.
That interview was hilarious! So his big trauma that caused him to come home crying to his mommy every day was that he had to practice with the rest of his team instead of partying? Man, this guy just becomes more of a prize every day. Get in line, ladies. He's mine!