(a) Len may not represent Fred to contest the Winny’s will, because such representation would be adverse to Harold.

      A lawyer must avoid conflicts of interest. A lawyer may not represent a new client in a matter that is adverse to a former client. A matter is adverse to a former client if it is the same or substantially the same matter.

      Here, Len previously drafted and executed both Harold and Winny’s wills. In drafting those wills, Len received confidential information from Harold that Sam would receive the Jackson Pollock painting regardless of who died first, based on an understanding that he had with Winny (see discussion below in part (b)). Now, Fred, Winny’s former spouse and Winny’s heir under Virginia’s intestacy statute, wants Len to represent him in contesting Winny’s will.

      Representing Fred would clearly be adverse to Harold, even though Harold is deceased. The duty of loyalty is a continuing duty which survives the death of the former client. The representation would be adverse because based on Harold and Winny’s wills, Sam is entitled to the Jackson Pollock painting, and representing Fred, who claims he is entitled to the painting, would cause Len to breach the continuing duty of loyalty he owes to Harold.

      There is an exception where a lawyer may represent a new client who is adverse to a former client if he receives the informed consent, in writing, from both clients. However, Harold is not able to consent because he is deceased. Additionally, even if Sam had the capacity to consent for Harold, he would not do so, given that he objected to Len representing Fred.

      Thus, no, Len may not represent Fred in contesting Winny’s will.

      (b) There likely was not an enforceable contract between Harold and Winny that precluded Winny from changing her will after Harold died. Contracts to make a will are not presumed in Virginia. Instead, a contract to make a will must be proved by clear and convincing evidence, either by extrinsic evidence; by the terms of the will itself; or by a contract itself.

      Here, it is unlikely that the facts show clear and convincing evidence of a contract to leave Sam the Jackson Pollock painting. Although there may be extrinsic evidence that Harold privately told Len that he and Winny had an understanding that Sam would inherit the painting regardless of who died first, this does not rise to the level of clear and convincing evidence. Additionally, if Len introduced evidence of this conversation, he would be breaching his continuing duty of loyalty and confidentiality to Harold, which survives even death of the client. Furthermore, nothing in the facts suggest that the terms of either will, or a separate contract, evidences a contract to leave Sam the painting by clear and convincing evidence

      (c) Winny’s note to Len is not sufficient to change her will.

      A will is invalid if it does not show present testamentary intent of the testator on its face. Wills may be either 1) typewritten and validly executed by the testator signing (or acknowledging a previous signature) in the joint presence of two witnesses and which the witnesses sign in the testator’s conscious presence, or 2) holographic (wholly in the testator’s handwriting and signed by the testator).

      Here, although Winny’s note met the requirement of a holographic will, because her letter to Len was wholly in her handwriting and signed by her, the note itself does not show Winny’s present testamentary intent. Testamentary intent requires that the testator show that she presently intends for the document to be her last will and testament. In this case, Winny’s note expresses that she wants to change her will, not that she is changing her will. Additionally, Winny states that she will call Len next week so that she can come by and discuss it with him. These facts strongly indicate that Winny did not intent for the letter to Len to operate as her last will and testament, and instead, that the letter was simply just instructing Len to draw up a new will. Therefore, the letter to Len does not show testamentary intent and is invalid.

      Thus, because Winny’s letter to Len lacked testamentary intent, it is insufficient to change her will.

3a) Len May Not Represent Fred to Contest the Will as it Would Violate His Duty of Loyalty to Winny and He May Be Called as a Fact-Witness Here

In Virginia, under teh Virginia Rules of Professional Conduct, an attorney is required to investigate potential representations for conflicts of interest or other reasons that may bar them from representing a client. If there is a substantial risk that a conflict of interest will materially limit their ability to represent a client, an attorney must get consent from the client in writing after consultation, if the attorney reasonable believes they can still provide diligent and competent representation, unless a conflict is sufficiently gross that it cannot be waived. However, lawyers also have a duty of loyalty to their past clients, and may not undertake representations for current clients that would be directly adverse or substancially related and adverse to a matter an attorney previously worked on for a prior client. In such a case, an attorney can only undertake the representation if both the former and current clients waive the conflict after consultation in writing. An attorney is also barred from representing a client if there is a substancial likelihood that an attorney will be called as a fact witness to a contested matter in a case.

Here, there is a gross conflict of interest. Len is the attorney who drafted Winny's first will and the attorney to whom the note at issue was sent. Len is therefore under an obligation of a duty of loyalty here to Winny, even though she is dead. As such, he cannot undertake this representation for Fred because it is substancially related to the matter he previously worked on for Winny, namely the will, and it is adverse to her interests in that it is an attempt to undermine her will that he executed. While Winny did mention to Len her intent to change her will regarding the painting, it would still be adverse to Winny's interests to attempt to throw out the original will. This is therefore a gross conflict of interest that cannot be waived. And even if it was waiveable, Winny is dead, and so therefore cannot consent to the representation. Her consent cannot be presumed and therefore a waiver of the conflict of interest cannot be obtained both from Fred and from Winny.

Further, there is a substantial risk that Len will be called as a fact witness here as to matters that are substancially in dispute. Specifically, in a contest for the will and the purported contract between Harold and Winny, Len would have to testify as the discussions he had, the note he received from Winny, and other relevant facts around the will and Winny's intent. As such, Len is also barred from representing Fred as he is likely to be fact witness of a disputed matter, another gross conflict that cannot be waived.

3b) There was No Enforceable Contract Between Harold and Winny Because the Requirements for a Contract or a Contract Concerning a Will Were Not Met and Such a Contract Would Not Divest a Person of Changing Their Will

In Virginia, it is possible for parties to contract for a will. To do so, the parties must have a clear and definite contract, for which the party seeking enforcement has performed, and the failure to enforce the contract would operate a fraud. For there to be a contract there must be an offer, acceptance, and consideration. Such a contract must be proven by clear and convincing evidence and if proven, would result in a constructive trust as to the matter at hand. Even if such a contract exists, a person always remains free to change their will, however, a constructive trust may prevent the distribution of property according to its terms.

Here, there does not even appear to be a contract. The only fact known about the supposed contract is that Harold at one point had an understanding with Winny that Sam would inherit the painting, regardless who died first. It is not clear, however, if Winny agreed to this and there was an actual contract or if it was merely an informal understanding that both sides consider freely revocable. It is also unclear if there was consideration for this contract, though such might arguable exist if both Winny and Harold mutually agreed for the painting to go to Sam. However, the single conversation with Len is not sufficient to show that there is a clear and definite contract. While Sam might be able to enforce it as, though he did not perform, he appears to have been the intended beneficiary, there is no evidence at all to suggest that failure to enforce the contract would work a fraud of Sam as there is no evidence Sam acted in any reliance on this promise. And given the paucity of evidence, it is particularly unlikely that any court would find there was a contract by clear and convincing evidence. Further, even if such a contract existed and even if Fred could enforce it, technically this would not bar Winny from changing her will and would only allow Sam to bring an action to enforce a constructive trust to gain possession of the painting.

Thus, there was no enforceable contract between Winny and Harold that prevented Winny from changing her will.

3c) Winny's Note to Change is Insufficient to Change Her Will Because it Cannot Be an Express Revocation Nor Does it Meet the Requirements for a Seperate Will Because it Lacks Testamentary Intent

In Virginia, a valid will is only revocable by certain limited acts. A testatory may revoke a will through a physicial act, such as striking through a portion of it or destroying it, though such destruction must be done in their presence. A testator may also revoke a will expressly through the execution of a new will in conformance with the requirements for a will or through contradiction by the execution of a new will, to the extent it contradicts the prior will. For a holographic, that is handwritten, will, the will must be in the testator's handwriting, must be signed by testator, must make clear its present testamentary intent, and must have two disinterested witnesses able to testify as to the testator's signature. A codicil, that is an amendment to a will, must also be executed with the same formalities as a will. Virginia also has a harmless error statute that will allow for a document to be potentially be a will, even if it does not conform to the formal requirements, so long it is a signed document and exhbits testimentary intent that the document is intended to be a will by clear and convincing evidence. Mere future intent to make a will is insufficient.

Here, to succeed, Fred would have to argue that the note is a revocation of her previous will or is itself an actual will. This Fred cannot do. Winny's handwritten note cannot give Len the power to modify or revoke Winny's will because any such act must take place in the testator's presence and at their direction. This means that the note may have instructed Len to prepare a document for execution, but did not empower him to modify Winny's will.

The note also fails to itself be a will or codicl that could modify Winny's prior will because it lacks present testamentary intent. Winny may have signed the will and it is in her handwritting, by there is no present intent for it to be a will or a codicil. Specifically, Winny talks of how she "would like to change" the will and how she "will call you next week to come by and discuss it with" Len. This strongly suggests that there is no present testamentary intent, but rather that it is a statement of future intent to change the will. Even though the note is signed, the Virginia harmless error statute does not help here as there is no present testamentary intent.

Therefore, Winny's note was not effective as a revocation or modification of her prior will because it could not empower Sam to modify Winny's will, nor did it show the necessary present testamentary intent to itself be a will or codicil to her previous will.