14 months from october 2018 (i.e. two thirds of the sentence) would be up in november 2019.
21 months from october 2018 (i.e. the full sentence) would be up in june 2020.
as he still seems to be applying for parole (two thirds of the sentence) the dates don't add up. so, is he serving another sentence on top of the drugs sentence? did he not go straight to prison in october 2018?
the other question is, why didn't he serve the 2011 suspended sentence when they had him in 2016?
My understanding of this apparent timeline discrepancy is this:
Shortly after CB went on trial for the abuse of his ex's daughter in April 2016, he did a bunk to Portugal. It's still not entirely clear how he managed to do this as you would have thought he'd have been held on remand. Anyway, somehow he managed to slip away before the official sentencing.
When he was then extradited back to Germany from Portugal in late 2017, he was ordered to serve the 15 month sentence for the abuse charge following the Braunschweig's High Court verdict made on October 7th 2017.
Then in August 2018, having served 10 months of the sentence, he was eligible to be released under the "two-thirds penalty" provision that Germany has. And because there was a *advertiser censored*-up (and then a delay) in adding the Sylt charge to the extradition warrant, the authorities had no choice but to let him leave prison on parole while they tried to sort it out.
CB then fled Germany and about 4 weeks later on September 27, 2018, CB was arrested in Milan and extradited back to Germany to serve out the 21-month Sylt sentence as should have happened originally.
As SleuthD pointed out though, if he began serving that sentence when it was ratified in October 2018, the dates of his appeal for release towards the end of 2020 didn't match up since he would have already completed the full 21 month sentence by that point.
What I think happened though is that when he was extradited back to Germany in 2018, he was ordered to serve out the remaining "third" of the abuse charge sentence as well, for breaching the terms of his parole by fleeing the country. So I think he served the remaining 5 months for that and then the 21 month sentence for the Sylt offence came into effect around March 2019.
If the court decides in favour of the prisoner within the framework of its prognosis, he has a right to release. However, he is not completely free then, the sentence is only suspended. This is, so to speak, a break from the prison system. He is under probation at least for the duration of the remaining sentence. He must show by law-loyal behavior that the decision to dismiss him early was correct. If he does not prove himself, the revocation of the probation is imminent and the remainder of the sentence must be “served”.
Will I be released from prison after two thirds of my sentence? - Criminal Law Germany