Separated at Birth?

(Former?) Red Sox Manager Terry Francona and Shia LaBeouf

(Thanks to Swagstein for the suggestion)

Separated at Birth?

Anna Nicole Smith's lawyer / boyfriend Howard K Stern and writer Bill Simmons

Separated at Birth?

WWE superstar Edge, overpaid Washington Nationals OF Jayson Werth and actor Michael Shannon

Separated at Birth?

Actor Eugene Byrd and NFL cornerback Nnamdi Asomugha

Separated at Birth?

NBA players Serge Ibaka (Thunder) and Elton Brand (76ers)

Separated at Birth?

Blue Jays pitching prospect Deck McGuire and actor Matthew Lillard

Separated at Birth?

A rock hyrax and San Antonio head coach Gregg Popovich

Separated at Birth?

Actor Chris Noth and Kentucky C Josh Harrellson

Separated at Birth?

American Idol contestant Casey Abrams and this red toy poodle.

Separated at Birth?

Shrek and Giants S Antrel Rolle