For a time, until the late 2010s, the Yankees didn’t usually hand too many contract extensions per se. It was just one of The Boss’ things. George Steinbrenner was a big spender in free agency, sure, but extensions weren’t really frequent.
He wasn’t opposed to re-signing hitters who entered the market after stints with the Yankees, though, which is what happened when Alex Rodriguez exercised his opt-out clause after the 2007 season. He was signed to a mammoth 10-year, $275 million pact that wasn’t technically an extension. But Steinbrenner did hand out a few notable deals to his players before they entered free agency, and after he ceded control of the team and passed, his sons did the same.