4. Honorable Mention: Derek Jeter: 10 Years, $189 Million
Technically signed one year prior to Jeter hitting free agency, the Yankees locked up their future Captain before the 2001 season, ending any drama for the next decade.
After this deal was signed, the only uncertainty remaining was, "How many celebratory Jello Shots could Jeter down, and where?"
Any time you can lock down an icon before he makes it to market, that decision's probably wise. Not a free agent deal, but still the fourth-richest contract this team has ever signed, meaning -- against all odds -- there are only three $200 million-plus contracts of any kind on this franchise's books all time.