2. LB Jessie Armstead
A truly beloved member of the NY Giants, Jessie Armstead was just more unlucky than anything to not win a super bowl with Big Blue.
Drafted in the 8th round of the 1993 draft, Armstead came in when expectations were high for the team coming off two recent Super Bowls. However, the team fizzled off a bit in the ’90s, and Armstead failed to win a Lombardi with the Giants before his exit in 2001 after an amazing nine-year career with the team.
A true rags-to-riches story, no one was anticipating that the former Miami Hurricane would do the types of things he did in the NFL as an 8th round pick. Yet, Armstead was a force at the linebacker position for the NY Giants, racking up 31.5 sacks, 12 picks, and two touchdowns during his time with Big Blue.
He was a true do-it-all linebacker that gave it his all every snap and was a total fan favorite. He did at least get to play in one Super Bowl, although again, it was a very one-sided loss against the historically great 2000 Baltimore Ravens.
During his time with the NY Giants, Armstead made five Pro Bowls and four All-Pro teams, showing just how lethal of a player he was.
Of all the great NY Giants to never win a Super Bowl with the team, this one is right up there at the top as the hardest to swallow.