After Oliver Cromwell's death was the Commonwealth doomed, because of structural factors, or a republic like the United Provinces could have survived but it failed because of contingency and individuals' actions? How guilty is Cromwell for not setting solid foundations for the continuity of the Commonwealth?
Yes, the Commonwealth was doomed after Cromwell's death, but the reason why is both structural factors and contingency/agency - because the actions of a few individuals (including but not limited to Cromwell) set those structural factors in motion.
In term's of Cromwell's guilt, I would say that he bears ultimate responsbility for the institutional weaknesses of the Commonwealth. To be totally fair, he did try to fix those weaknesses repeatedly - but because of the actions he took at the beginning that set up the structural factors in question, those efforts came to naught.
That's the TLDR, I'll do the specific explanation below the cut, because it's going to go long.
Background
Just to make sure everyone's on the same page: in 1640, Charles I is forced to call Parliament even though he hates doing it. He dissolves Parliament after three weeks. (Hence why it's called the Short Parliament.) He's then forced to call Parliament again, and this Parliament is the Long Parliament. The Long Parliament enacts a whole series of legislation that Charles I hates, and then in 1642 the conflict between King and Parliament breaks out into the First English Civil War (1642-1646).
During this first phase of the conflict, it takes a while for Parliament and the Parliamentary generals to get their act together. Things begin to turn around in 1644 when the Scottish Covenanters join the war on Parliament's side and they win the Battle of Marston Moor - which gives Parliament control of the North of England and is the first battle where Cromwell plays a major role. The next year, Parliament gets rid of the original Parliamentary generals through the Self-Denying Ordinance, forms the New Model Army under Fairfax and Cromwell (the one guy specifically exempted form the Self-Denying Ordinance), and Fairfax and Cromwell go on to completely destroy the Royalist armies at Nasby and Langport.
Charles hangs on for a bit, but is eventually captured in 1646 and the first Civil War ends. The question is now: what do we do, now that Parliament has won?
The Putney Debates
Once the fighting was over, the political fighting could begin and it was quite complicated. You had the Long Parliament, which was dominated by the moderate "Presbyterian" faction who had been locked out of military power by the Self-Denying Ordinance. You had the New Model Army, which was religiously Puritan but split politically (more on this in a second). You had the Scots, politically constituted by the Scottish Parliament and militarily represented by the Covenanter armies, who wanted Presbyterianism to be extended throughout Britain. And then you had the Royalists and Charles I, who were usually but not always the same faction.
I'm going to focus here on the part of this conflict that involved the Long Parliament and the New Model Army. The Long Parliament wants to do a deal with Charles I - although the problem is that Charles is stretching out negotiations in the hopes that if everything collapses into anarchy he might get himself back on the throne - it wants a unified British Presbyterian Church established (because it had kind of agreed to set one up as the cost of getting Scottish support during the war), and it wants to get rid of the New Model Army which it views as dangerously radical and way too powerful.
The New Model Army isn't sure what it wants, because it's split between the Agitators (i.e, the Levellers) and the Grandees (the senior officers of the Army, led by Cromwell and Fairfax) - although the one thing both sides agree on is that they're not going to accept a single established Presbyterian Church and that they aren't going anywhere until they get their back pay and some sort of reforms happen that justify four years of civil war.
In the mean-time, everyone's getting very testy. First, the Long Parliament orders the New Model Army to disband in early 1647. The New Model Army refuses to disband. Then the New Model Army takes control of the prisoner Charles I in early June. In late June, a pro-Presbyterian mob invades Parliament calling for an established Presbyterian Church and for Charles I to be brought to London, causing all of the Independent (i.e, Puritan) MPs and the Speaker to flee the city and seek the protection of the New Model Army. Then in August, the New Model Army marches on London, and forces Parliament to enact a Null and Void Ordinance undoing everything the Long Parliament had done since June, which causes the Presbyterian MPs to withdraw from Parliament (temporarily), which means the Independents are now in the majority.
All of this is very confusing, and no one in the New Model Army is sure what to do now that they hold all the cards. So the New Model Army decides to have a public debate at Putney in late October in order to hash out what the Army's position is going to be.
At Putney, both sides put forward manifestos for what the Army should stand for. The Agitators put forward the "Agreement of the People," which calls for:
the Long Parliament to be dissolved and elections to be held for a new Parliament.
these elections to be held after a reapportionment of Parliament to establish equal districts on the basis of one-man-one-vote.
elections for a new Parliament every two years.
the electorate to be made up of "all men of the age of one and twenty years and upwards (not being servants, or receiving alms, or having served in the late King in Arms or voluntary Contributions)." (i.e, fairly universal male suffrage).
Parliament is to have full Executive and Legislative authority, except that the people shall have liberty of conscience, freedom from conscription, equality before the law, and there shall be amnesty for anything done or said during the Civil War.
The Grandees, who freaked the fuck out when they heard these terms and started immediately calling the Agitators "Levellers" (i.e, 17th century for "commie bastards"), put forward the "Heads of Proposals," which calls for:
the Long Parliament to be dissolved and elections to be held for a new Parliament.
these elections to be held after Parliament decides on "some rule of equality of proportion...to the respective rates they bear in the common charges and burdens of the kingdom," or on the basis of some other rule that will make the Commons "as near as may be" to equally proportioned.
for the next ten years, Parliament and not the King has authority over the military, finances, and the bureaucracy.
for the next five years, Royalists aren't allowed to run for elected office or hold appointed public offices.
the Church of England will continue to exist, but you don't have to read the Book of Common Prayer if you don't want to, you don't get fined for not going to CoE services or attending other services, and there will be no imposition of a Presbyterian Covenant.
You can see that there are some overlapping areas (no more Long Parliament, elections every two years, some form of reapportionment, some form of liberty of conscience) but there are some really significant differences - a republic versus a constitutional monarchy, a unicameral Parliament versus retaining the House of Lords, and universal suffrage versus property requirements.
During the Putney Debates, Cromwell flatly refuses to accept anything other than a constitutional monarchy, Ireton (Cromwell's son-in-law) refuses to accept universal suffrage, but the two sides agree that a committee will work out a compromise on the basis of everything else from the "Agreement" as long as the Agitators agree to go back to their regiments.
Then the King escapes from captivity and everyone panics. Cromwell and Fairfax scramble a new manifesto together and try to get the New Model Army to approve that manifesto along with everyone taking a loyalty oath to Fairfax and the General Council of the Army, the Agitators see this as a stab in the back and start up a mutiny, and Cromwell and Fairfax crush the mutiny and arrest the Agitator leadership. In late November 1647, Charles I, who has been recaptured by this point, signs a secret agreement with the Scots to invade England and restore Charles to the throne in return for Presbyterianism being established in England.
The Second Civil War
Things slow down for a bit, because the Scots are actually quite divided about this agreement - the Kirk actually condemns it as "sinful" - and it takes until April for the pro-agreement faction (known as the "Engagers") to get a majority in the Scottish Parliament.
In May 1648, Royalist uprisings break out across the kingdom, with South Wales, Kent, Essex, and Cumberland being particular centers of Royalist strength, and the Scottish Covenanter army crosses the border and invades England. Unfortunately for Charles, the Royalists, the English Presbyterians, and the Scots, they completely fail to coordinate their actions and the New Model Army is able to completely crush the uprisings one-by-one and then turns its attention to the Scots.
At the Battle of Preston in August 1648, the New Model Army under Cromwell wins another one of its ridiculously lopsided victories that make his emerging belief that he had been chosen by God somewhat understanable, and the formidable Covenanter army is crushed.
By this point, Cromwell and the rest of the Grandees are convinced of two things: one, no more negotiating with the King. As the Army Council put it rather ominously, it was their duty "to call Charles Stuart, that man of blood, to an account for that blood he had shed, and mischief he had done." Two, the (English) Presbyterians could not be trusted. They had conspired with the King and their Scottish co-religionists to overthrow the government and abolish religious liberty, and thus they had to go.
Thus, in December 1648, Pride's Purge is carried out, in which a detachment of troops acting under orders from Ireton (and thus from Cromwell) bar 140 MPs from taking their seat and arrest 45 of them. This effectively ends the Long Parliament, and the remaining 156 MPs continue to sit as the Rump Parliament. In the New Year, the Rump Parliament then votes to put the King on trial for treason and then afterwards establishes the Commonwealth as a unicameral Republic.
What Comes Next?
You'll note a couple things at this point: first, Cromwell's political positions are fairly fluid and change with events, so that he goes from being a staunch constitutional monarchist in late 1647 to a determined regicide by January 1649. Second, even though it's been a few years since the Putney Debates, Cromwell and the Grandees haven't implemented the "Heads of Proposals" - most crucially, they haven't dissolved Parliament and called for new elections, nor has a new Constitution been established.
Initially, one might say that Cromwell was distracted by his campaign to crush the Confederate-Royalist coalition in Ireland and then to crush the alliance between the Covenanters and Charles II. But by 1651, he's back in England and there's still no election and still no Constitution. Cromwell tries to get the Rump Parliament to call for new elections, establish a new Constitution that incorporates Ireland and Scotland now that they've been conquered, and finds some sort of religious settlement.
For two years, the Rump Parliament deadlocks on practically everything except the religious settlement, where it manages to piss off everyone by keeping the Church of England and its tithes, but also getting rid of the Act of Uniformity and allowing Independents to worship openly, but also passing all kinds of Puritan moral regulations. In April of 1653, Cromwell proposes that the Rump Parliament establish a caretaker government that will deal with the Constitution and new elections, but the Rump deadlocks on that too. This causes Cromwell to completely lose it and dissolve the Rump Parliament by force, culminating in one hell of a speech:
It is high time for me to put an end to your sitting in this place, which you have dishonoured by your contempt of all virtue, and defiled by your practice of every vice; ye are a factious crew, and enemies to all good government; ye are a pack of mercenary wretches, and would like Esau sell your country for a mess of pottage, and like Judas betray your God for a few pieces of money.
Is there a single virtue now remaining amongst you? Is there one vice you do not possess? Ye have no more religion than my horse; gold is your God; which of you have not barter'd your conscience for bribes? Is there a man amongst you that has the least care for the good of the Commonwealth?
Ye sordid prostitutes have you not defil'd this sacred place, and turn'd the Lord's temple into a den of thieves, by your immoral principles and wicked practices? Ye are grown intolerably odious to the whole nation; you were deputed here by the people to get grievances redress'd, are yourselves gone! So! Take away that shining bauble there, and lock up the doors. In the name of God, go!
Now there's no more Parliament and Cromwell and the Council are running the country on their own, but they don't have a plan for what to do next. A Fifth Monarchist member of the Council proposes appointing a "sanhedrin of saints" on the basis of religious credentials who will set up a godly commonwealth and bring about the imminent return of Christ. That doesn't happen, but the Council does like the idea of an appointed (rather than elected) body called the Nominated Assembly, which becomes known as Barebone's Parliament. This Parliament doesn't make it a year because of how badly it's divided between moderate republicans who want a functioning government and Fifth Monarchists who believe that Jesus Christ is coming back to Earth any day now, so why bother? Ultimately, Barebone's Parliament dissolves itself.
This then leads the Council to pass the Instruments of Government, which was essentially an adapted version of the original "Heads of Proposals." Under the Instrument, Executive power would be held by the Lord Protector who would serve for life, Legislative power would be held by a Parliament elected every three years, and then there would be a Council of State appointed by Parliament which would advise and elect the Lord Protector upon the death of the previous occupant. Thus, the Protectorate is born.
In 1654, Cromwell finally manages to get the First Protectorate Parliament elected...and it only lasts a single term, agrees to none of the 84 bills that Cromwell and the Council of State, and is promptly dissolved as soon as the Instruments would allow. And so on it went through the Second and Third Protectorate Parliaments, and then Cromwell died and the rest is history.
Conclusion
Coming back to what I mentioned at the very beginning about the interplay between structural factors and individual actions, I think we can see a kind of ratchet effect whereby decisions taken early on that foreclosed certain options compound on each other over time, leading to structural factors that weakened the Commonwealth.
The crucial turning point(s) to me are the decision to reject the Agreement of the People in 1647 and then the failure to enact the Heads of Proposals in 1647 after the Putney debates, or in 1648 or 1649 after Pride's Purge.
With the Agreement, you could have had a small-d democratic republic which would have offered ordinary working people new political rights and protections and the opportunity to buy-in to the new regime through an election for a new Parliament. With the Heads of Proposals, you could have had a more conservative republic that would have offered much the same to the traditional landed political class, which would have then granted their consent to the new regime by both standing for election and voting in that election for a new Parliament.
That kind of legitimacy was absolutely necessary in order to ensure the long-term allegiance of the population to the new regime in the face of Royalist revanchism, let alone the kind of radical changes (putting the king on trial, declaring a republic, establishing a religious settlement) that Cromwell and the Grandees saw as essential.
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