ˈæftɚ ðə dˈɛθ ʌv hɪz fˈɜːst wˈaɪf ˈoʊkli mˈæɹid mɐtˈɪldə kɹˈuːɡɚ wˈʌn θˈaʊzənd ˈeɪthˈʌndɹɪd nˈaɪn wˈʌn θˈaʊzənd ˈeɪthˈʌndɹɪd nˈaɪnti wˈʌn; ðə dˈɔːɾɚɹ ʌv hˈɛnɹi kɹˈuːɡɚ, hˌuː hæd ðə juːnˈiːk dɪstˈɪŋkʃən ʌv sˈɜːvɪŋ æz bˈoʊθ ɐ mˈɛmbɚɹ ʌv pˈɑːɹləmənt wˈʌn θˈaʊzənd sˈɛvənhˈʌndɹɪd sˈɛvənti fˈoːɹ wˈʌn θˈaʊzənd sˈɛvənhˈʌndɹɪd ˈeɪɾi; wˈʌn θˈaʊzənd sˈɛvənhˈʌndɹɪd ˈeɪɾi fˈoːɹ wˈʌn θˈaʊzənd sˈɛvənhˈʌndɹɪd nˈaɪnti ænd æz ɐ nˈuː jˈɔːɹk stˈeɪt sˈɛnəɾɚ wˈʌn θˈaʊzənd sˈɛvənhˈʌndɹɪd nˈaɪnti tˈuː wˈʌn θˈaʊzənd sˈɛvənhˈʌndɹɪd nˈaɪnti sˈɪks.
After the death of his first wife Oakley married Matilda Cruger (1809–1891); the daughter of Henry Cruger, who had the unique distinction of serving as both a member of Parliament (1774–1780; 1784–1790) and as a New York State Senator (1792–1796).