Guest Stars Richard Herd as Milton Cooper Chris Mulkey as William Pettifer Co Starring Ma'a Tanuvasa as Guard Mariano Farrar as Clarence Whitmour Daisy Kim Murakami as Yuki Uncredited Meaghan Rath as Alexa Alana Ian Anthony Dale as Earl Blackstone Beulah Koale as Evan Kekoa Scott Caan as Milton Cooper - 1941 Chi McBride as Capt. Charles Sumner Alex O'Loughlin as Steven McGarrett Sr - 1941 Taylor Wily as "Biggie" Tupa Jorge Garcia as Officer Mike Flanagan Dennis Chun as Sgt. Naskiuchi