Can the president issue a blanket pardon or does he need to enumerate each crime being pardoned?

What do you mean by “could [he] enter”?

I think that the contract would be unenforceable. Traditional contract principles would tend to suggest that.

Would the pardon be valid? I think so, but there’s no clear answer. I am skeptical (and think i court would be as well) of any effort to restrict the pardon power beyond what’s provided in the constitution.

Would the president have committed a crime by entering to such an agreement (or providing such a pardon)? Maybe. You could certainly convince me. (But again, I think it would be a uphill battle to criminalize the president’s exercise of his specifically-granted powers).

Would it be impeachable? (I know some posters disagree with me but), the “modern” view is that anything is impeachable and, as a result, the president and all executive and judicial officers serve at the pleasure of the legislature. But even if that wasn’t true, it would certainly seem like the type of misuse of office that would fall within the traditional notion of “high crimes and misdemeanors”.

You don’t have to admit guilt; some states still allow an Alford plea— a defendant does not admit to the crime and asserts their innocence. But does admit their is enough evidence to prove they have committed the crime beyond a reasonable doubt.

Elements of a contract are:

  1. Mutual assent, expressed by a valid offer and acceptance
  2. Adequate consideration
  3. Capacity
  4. Legality

You could not have the contract force a pardon but you could write a contract with financial penalties for non-performance. For instance, if I contract with someone to paint my house and they refuse to do that I cannot force them to paint it but I can get financial damages for non-performance.

Why would that not work here?

Interesting. Is that a distinction without a difference? How often does it happen that way?

If the judge decides that a plea bargain is objectively fair, they still need to make sure that the defendant actually committed the crime that is the subject of the guilty or no contest plea. This involves a conversation between the judge and the defendant, in which the defendant will need to admit under oath certain facts that show their guilt. In this conversation, the judge also needs to make sure that the guilty plea is knowing and intelligent. The defendant must understand the rights that they are waiving, such as the right to a jury trial, the right to confront the prosecution’s witnesses, and protections against self-incrimination. If the defendant is not represented at this stage, they will need to waive the right to counsel. They also must understand the charges and their obligations under the plea agreement, including the sentence that will be imposed. The defendant should be aware of the range of sentences that they could receive if the case went to trial.

SOURCE: https://www.justia.com/criminal/plea-bargains/finalizing-a-plea-bargain/

You can’t enforce a contract that is against “public policy.” It’s a messy area, but one of the clearest examples would be a contract to do something illegal. It’s seldom as interesting as we’re supposing (a common example is a contract to perform some work that you are not properly licensed to do), but our hypothetical is a pretty straightforward example.

Don’t make the contract to do something “illegal” in the contract. Make the contract to carry out the will of the president for the term of the contract. That could be, “Get me a Big Mac.”

I would assume that the president can enter into an employment (or other) contract with someone, sure.

But if we’re imagining crimes committed and a pardon promised and a breach of the contract (by either president or goon), you’re going to be quickly into “contrary to public policy” territory. Because you’re going to have to prove breach and damages in this hypothetical case.

Twelve years later, in Biddle v. Perovich, the court hinted that it no longer believed in the necessity to “accept” a pardon. They ruled that a convict has no right to reject a commutation, and a commutation is an exercise of the pardon power. They also said the Solicitor General’s argument that no acceptance was necessary for any pardon was “very persuasive.”

Suppose we were back in the days when corporal punishment was a thing.
You are convicted, and sentenced to 100 lashes.
The president gives you a pardon.
The executioner does not flog you.
Whether or not you accepted the pardon is irrelevant to the State.

It may be irrelevant to the state but it might be relevant to you.

While most people would be happy to avoid punishment there are more than a few cases of people wanting to endure the punishment to make a political statement.

Also, if we went with a pardon meaning an admission of guilt (which I know is far from settled in this thread) then some people may well want to refuse the pardon because they want to assert their innocence.