NEW YORK—There were times when Josh Hamilton imagined playing alongside old Tampa Bay pals Carl Crawford and Rocco Baldelli in the World Series.

Like the devil’s head inked on the crook of his left elbow—one of his 26 tattoos—those thoughts faded.

“That would’ve been a heck of an outfield. Carl, Rocco and me, running balls down, throwing guys out, hitting home runs,” Hamilton said this week during a Manhattan visit. “It would’ve been awesome to play with them.”

“It just wasn’t in the cards,” he said.

Then again, the Texas Rangers star already won...

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