5 best free agent fits for Chicago Bears to replace Eddie Jackson

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4. Should the Chicago Bears pursue Jordan Whitehead this offseason?

Geno Stone and Jaquan Brisker both grew up in the Pittsburgh area, but so did Jordan Whitehead, who went to Pitt. He started his career with the Tampa Bay Buccaneers but really broke out last year with the New York Jets. 

One of the big differences between his time with the Bucs and the Jets is that he started to play the deep safety role a lot more. For example, he had 1,213 snaps as the free safety in the Bucs' defense over four years. In two years, he had 1,23 snaps as the free safety in the back end. 

This has caused Whitehead to play at his best. Now, he is set to hit free agency again and his stock is much higher than the first time around. He knows how this goes and will likely want to hold out for the highest bidder. It may help that the Chicago Bears hold the cap situation cards as we enter the offseason. Simply put, if the Bears think Whitehead is a fit next to Jaquan Brisker, nothing can stop them from making it happen. Does it happen?