Эстес, в надежде на обещанное смягчение приговора, без зазрения совести свидетельствовал на суде против своих компаньонов. В итоге суд приговорил Генри Старра к двадцати пяти годам тюрьмы, Максфилда к семи, а Сойера к пяти. Адвокату Чарльза Джонсона удалось показать противоречивость показаний Эстеса против его подзащитного и снять с Джонсона все обвинения. Льюис Эстес тоже получил по заслугам… пять лет тяжелых каторжных работ.
Оказавшись в тюрьме, Старр снова начал вести себя примерно и говорить о необходимости жить честно, убеждая молодежь не совершать ошибок, допущенных им.
«Мне уже 45 лет, — сказал он репортеру газеты «Oklahoma World», — и 17 из этих 45 я провел в тюрьме. Разве этого не достаточно, чтобы показать любому мальчишке, что в моей прежней жизни нет ничего хорошего?» И снова харизма Генри Старра и его «правильные слова» сыграли свою роль. В 1919 году он был помилован.
Два года Генри вел честную жизнь. Он увлекся кино и даже снял фильм «Должник закона», в котором сыграл одну из ролей. Фильм рассказывал об ограблении в Страуде, раскрывая негативные стороны жизни преступного мира. Фильм имел оглушительный успех. Личная жизнь Генри тоже налаживалась. В феврале 1920 года он женился на девушке, которая была моложе его на 24 года.
Но оставить своих прежних привычек Генри так и не смог. Почти ровно через год после женитьбы, 18 февраля 1921 года, он въехал на скоростном автомобиле в город Харрисон, штат Арканзас. С ним были три его компаньона. Входя в Народный государственный банк Генри не знал, что дни его сочтены. Пуля, выпущенная из дальнего угла зала, сбила его на пол.
Генри Старр умер через четыре дня после ограбления. Рядом с ним были жена, мать и сын. Незадолго до того, как сделать последний вдох, он с легкой гордостью в голосе проговорил:
— Я ограбил больше банков, чем любой другой человек в Америке…
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