During Wat Tyler’s Rebellion the Tower of London was sacked and royal officials were executed. Among the royal officials was Henry of Bolingbroke, who by virtue of being the son of John of Gaunt was also in danger. Fortunately for Henry he was saved by John Ferrour. But what if John hadn’t saved Henry? What if Henry was killed during the rebellion? Assuming the rebellion is still squashed, this is going to look bad for Richard, due to his failure to protect his cousin and officials. Gaunt’s also going to be in mourning and in need of a male heir. He might attempt to legitimise the Beauforts or try to have another son with Constance of Castile to make up for that (as of now the latter is more likely). Mary de Bohun would possibly go to the Convent here, as Thomas of Woodstock wanted (which increases his power as he gets the full Bohun inheritance). How would this affect the succession? Would Richard declare the Mortimers his heirs earlier? What else might change.
 
The death of a prince of the blood would take a considerable amount of shine off of Richard's quashing of the rebellion. This has immediate consequences for the government of the realm. Firstly, Richard assumed personal control of government in the wake of the revolt, despite being just 14. This was acceptable in part because the "permanent council" system that had been set up after Edward III's death had been a miserable failure and also in part because Richard came away from the revolt looking like a hero to the nobility. That's not the case here and might mean that the council system continues on into the mid 80s.

Secondly, and most dangerously for Richard, Gaunt may come away from this blaming Richard for Henry's death. Gaunt protected Richard throughout his life. Richard's childhood reign 1381-1386 is basically a series of incidents in which Richard fucks up badly, everyone wants to get rid of the kid and/or the people around him, and then Gaunt and Joan of Kent swoop in to calm everyone down. It's not a coincidence that there's a rebellion almost the moment Gaunt and Joan are out of the picture or that Richard, after two years of political impotence, is able to overthrow the government of the Lords Appellant upon Gaunt's return. But does Gaunt bother to play this role in ATL? Or does Gaunt let Richard destroy himself even more quickly in ATL?

He might attempt to legitimise the Beauforts or try to have another son with Constance of Castile to make up for that (as of now the latter is more likely).
Gaunt repudiated Katherine and reconciled with Constance after the revolt in OTL. They may have tried having more children after that, as there is some evidence (though it is very slim) that Constance was pregnant in 1386. I think it is a guarantee that the two try for more children in ATL.

Mary de Bohun would possibly go to the Convent here, as Thomas of Woodstock wanted (which increases his power as he gets the full Bohun inheritance).
I suspect that Richard may try to push the girl onto his landless half-brother, John.

How would this affect the succession? Would Richard declare the Mortimers his heirs earlier? What else might change.
The Mortimers get an awful lot of attention in retrospect thanks to the Wars of the Roses, but there's almost no actual evidence that Richard wanted them as his heirs. On more than one occasion Richard tried to destroy the Mortimers, just as he did the Lancastrians.

edit: I'll clarify, there is a chronicle reference to Richard announcing the fourth earl of March as his heir, but there's no government record that he actually changed the line of succession in this way -- no act of parliament, no letter patent, nothing. Considering that the parliament in question is 1386, it's clear that the pronouncement before parliament was only done to counter the threat to depose him (i.e., to threaten the ascension of an even younger boy king).
 
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The death of a prince of the blood would take a considerable amount of shine off of Richard's quashing of the rebellion. This has immediate consequences for the government of the realm. Firstly, Richard assumed personal control of government in the wake of the revolt, despite being just 14. This was acceptable in part because the "permanent council" system that had been set up after Edward III's death had been a miserable failure and also in part because Richard came away from the revolt looking like a hero to the nobility. That's not the case here and might mean that the council system continues on into the mid 80s.
Agreed. It’s one thing for a revolt to be defeated but kill numerous officials in the process. It’s another for it to kill a Prince of Blood and the second-in-line to the throne. Richard not gaining power until he is older would be interesting, it’d probably slow down the rise of some of his favourites such as Michael de la Pole. Could this lead to some people seeing Richard as a hopeless case?
Secondly, and most dangerously for Richard, Gaunt may come away from this blaming Richard for Henry's death. Gaunt protected Richard throughout his life. Richard's childhood reign 1381-1386 is basically a series of incidents in which Richard fucks up badly, everyone wants to get rid of the kid and/or the people around him, and then Gaunt and Joan of Kent swoop in to calm everyone down. It's not a coincidence that there's a rebellion almost the moment Gaunt and Joan are out of the picture or that Richard, after two years of political impotence, is able to overthrow the government of the Lords Appellant upon Gaunt's return. But does Gaunt bother to play this role in ATL? Or does Gaunt let Richard destroy himself even more quickly in ATL?
That would be very interesting. Gaunt abandoning Richard out of spite, would be interesting, though he might continue to support him (but still dislike him) in case people take his abandonment of Richard as a sign of him planning to take the throne, which could make him even more unpopular. He could also try and guilt trip Richard into showing him and his family extra favour.

Though if Richard does destroy himself sooner than OTL, would he still be deposed? Gaunt might still be unpopular, so unless he has a son who is really popular the people might opt for someone else (probably Mortimer). They could also just install a council of nobles to do all the ruling for him, effectively defanging him.
Gaunt repudiated Katherine and reconciled with Constance after the revolt in OTL. They may have tried having more children after that, as there is some evidence (though it is very slim) that Constance was pregnant in 1386. I think it is a guarantee that the two try for more children in ATL.
Make sense. If they managed to have a son how would that affect the Castilian situation? Would Gaunt continue to pursue the Kingdom or would he make peace like OTL. Or would it fizzle out and later restart when their son (John) gets older.
I suspect that Richard may try to push the girl onto his landless half-brother, John.
Makes sense, it would make him a decently powerful noble to support Richard (which he’ll need).
The Mortimers get an awful lot of attention in retrospect thanks to the Wars of the Roses, but there's almost no actual evidence that Richard wanted them as his heirs. On more than one occasion Richard tried to destroy the Mortimers, just as he did the Lancastrians.
I had forgotten that Richard wasn’t fond of the mortimers himself. Would he instead play the Gaunt against the Mortimers to keep him occupied?
That benefits nobody
It benefits John and by consequence Richard, since his brother is more powerful and can help support him through any trouble he runs into.

Also If I am not mistaken, wouldn’t some of Henry of Bolingbroke’s go to his sisters, making them heiresses? If so, who would Gaunt marry them of to in order to make allies?
 
If they managed to have a son how would that affect the Castilian situation? Would Gaunt continue to pursue the Kingdom or would he make peace like OTL. Or would it fizzle out and later restart when their son (John) gets older.
I suspect they would fight harder, so that John's son could inherit.
 
I suspect they would fight harder, so that John's son could inherit.
That does make sense, especially if John becomes completely estranged from his nephew. I could also see him giving up for a while, only for his son to restart the cause. The son could also marry Lucia Visconti for irony’s sake.
 
That benefits nobody
It benefits the king's half-brother at a time when wedding heiresses was the preferred way to members of the royal family.

Could this lead to some people seeing Richard as a hopeless case?
I don't think he'd be seen as "hopeless" like people would just give up on him. It may sharpen criticism of the rotating door of men who made up his "continuous council," leading to another call for mass resignations (the turnover of the membership of the council was very high in OTL) or the appointment of a single, more powerful regent -- or, who know, maybe that leads to Richard taking the reigns at much to young an age in ATL as he did in OTL.

Though if Richard does destroy himself sooner than OTL, would he still be deposed?
If Gaunt has no interest in saving Richard from himself and Bolingbroke isn't around to rein Gloucester in, then I would say it's a safe bet that deposition comes earlier in ATL.

Make sense. If they managed to have a son how would that affect the Castilian situation? Would Gaunt continue to pursue the Kingdom or would he make peace like OTL. Or would it fizzle out and later restart when their son (John) gets older.
Gaunt's military failure in Castile seems to have crushed his interest in pursuing the throne, so I imagine it would fizzle out. (Though, if Constanza was pregnant at this time, it's possible part of Gaunt's loss of interest was caused or compounded by a stillbirth around this time.)

Would he instead play the Gaunt against the Mortimers to keep him occupied?
It's seems unlikely that Bolingbroke's death butterflies the death of the 3rd earl of March in Ireland. I'm not sure how or why Richard could play Gaunt off the seven-year-old 4th earl.
 
I don't think he'd be seen as "hopeless" like people would just give up on him. It may sharpen criticism of the rotating door of men who made up his "continuous council," leading to another call for mass resignations (the turnover of the membership of the council was very high in OTL) or the appointment of a single, more powerful regent -- or, who know, maybe that leads to Richard taking the reigns at much to young an age in ATL as he did in OTL.
All of those scenarios would be interesting. I'd imagine if a single regent was appointed they'd have to be more neutral, since Gaunt isn't going to want someone who dislikes him in charge and the people probably don't want him in charge. Maybe Edmund of York could serve as Regent? Letting Richard take charge sooner would also be interesting, especially if Gaunt leaves him to his own devices entirely since it could lead to Richard messing everything up sooner as you mentioned.
If Gaunt has no interest in saving Richard from himself and Bolingbroke isn't around to rein Gloucester in, then I would say it's a safe bet that deposition comes earlier in ATL.
That would be interesting. Though if he is deposed and still lacking an heir, who would become King? Gaunt's hardly going to let Gloucester or anyone else jump ahead of him in the succession, but at the same time, unless Richard's failure in the peasant revolt increases Gaunt's popularity, few are going to want him to be King. They could alternatively just declare him mad and establish a regency council if they want to avoid a civil war.
Gaunt's military failure in Castile seems to have crushed his interest in pursuing the throne, so I imagine it would fizzle out. (Though, if Constanza was pregnant at this time, it's possible part of Gaunt's loss of interest was caused or compounded by a stillbirth around this time.)
I see, so most likely it fizzles out and then maybe restarts if Gaunt has a son who is willing to try and reclaim his throne. Would Katherine still marry Henry III if Gaunt had a son, or would she marry elsewhere?
It's seems unlikely that Bolingbroke's death butterflies the death of the 3rd earl of March in Ireland. I'm not sure how or why Richard could play Gaunt off the seven-year-old 4th earl.
Hmm, that is true. I guess Mortimer recedes into the background until he comes of age.
 
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