The short answer is that a history of incarceration does not automatically mean someone will be held longer or receive a harsher sentence. What matters most is what the judge orders at sentencing.
Once a judge commits an individual to a specific sentence and custody level, that is what they will serve. Under federal sentencing guidelines, most inmates serve approximately 85% of their imposed sentence, with the remaining time accounted for through good time credit, earned by maintaining good behavior throughout their incarceration.
Prior criminal history does play a role, but it is factored into sentencing through the federal criminal history scoring system, which assigns points based on past convictions. A higher criminal history score can result in a longer recommended sentence under the guidelines, but the judge retains discretion and is not strictly bound by those recommendations.