I'm trying to scrape from the following website
Specifically, I'm trying to obtain the player's draft position, aka "X overall" which appears in the line
1st round (3rd pick, 3rd overall)
var rawText = page.plainText;
var regExp = /pick, ([\d]+)\w\w overall/;
var matches = regExp.exec(rawText);
Your regex seems fine (the match below works) so there must be something wrong with the string you're matching against.
console.log("1st round (3rd pick, 3rd overall)".match(/pick, ([\d]+)\w\w overall/));