NinerSickness
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I think one of the flaws with your OL analysis is that Joe Thomas was (is) considered the best LT in the league. Jake Long is coming off an injury riddled season where he didn't perform like an elite LT.
I did consider that. That's why I listed him 3rd. I was having a hard time finding the record-breaking OLT contracts over the years, so I don't have a huge sample size yet. I just remembered Freeney & Mario broke records in that respect. Joe Thomas had the biggest in history so far if I'm not mistaken.
The weird thing is that Steve Hutchinson was the highest-paid OL in the league at one point as a guard. That was the year a lot of record-breaking contracts were signed if I remember correctly.