1. Tony Boselli – Retired at 29 in 2002

The 1990’s could be referred to as “The Golden Age of left tackles in the NFL.” A few of them have already been inducted into the NFL Hall of Fame (Orlando Pace and Jonathan Ogden). But Tony Boselli might’ve been the best of them all, and would’ve been well on his way to an enshrinement in Canton had his career not been cut short by injury.

The first ever selection of the Jacksonville Jaguars franchise was one of the early “genetic freaks” at left tackle, showing remarkable athleticism for a man that stood 6’7 and weighed 320lbs. He was a five time Pro Bowl selection and three time All Pro in his six year career. His career came to a premature end due to an injury to his left shoulder, a result of years of weightlifting and constant pounding. Boselli attempted a comeback with the Houston Texans, but he was never healthy enough to make it onto the field.