Highland Cup 2025 - Lessons Learned as a Finalist

By Caitlin Whittier 

My name is Caitlin Whittier. I am a fifth year student and external moot director for the LSOU. Beyond my wildest imagination, I made it to the final round of the Highland Cup Mooting Competition of 2025 as a second-time mooter, alongside my partner who was mooting for the first time. For those of you who have never mooted before, essentially what it entails, is analyzing the respondent and appellant factums of the court case, creating submissions grounded in relevant legal principles cited in the case, then taking on the role of a lawyer in front of a judge and responding to questions on the spot. This is a valuable experience for learning how to think on your feet, and gain the argumentative skills of a real lawyer! 

Facts of the Case (R. v. Underwood, 2025) 

● Buddy Ray Underwood, in a joint enterprise with 4 accomplices, committed numerous offences, such as kidnapping and unlawful confinement, prior to killing a woman named Nature Dupperon through an overdose of fentanyl injections. 

● (Appellant position) The trial court convicted Underwood of second-degree murder, finding that the murder was not committed according to a plan, as required under section 231 (2) of the criminal code. Additionally, they did not find him to be a substantial and integral cause of the victim’s death, specifically because the victim died from fentanyl injections, in which none were directly administered by Underwood himself. He was more so an “intimidating force” for his accomplices. 

● (Respondent position) On appeal, Underwood’s sentence was increased to first-degree murder, due to the finding of two legal errors with the trial judge’s analysis of planning and the substantial cause test. This court found that there was a significant level of planning involved and Mr. Underwood played a substantial role, leading to the victim’s death. 

● The increased conviction to first-degree murder was a unanimous decision by the Alberta Court of Appeal, making it a particularly difficult case for the appellant. 

First-degree murder - section 231 (2) and 231 (5) of the Criminal Code Under section 231 (2), first-degree murder requires;

(a) Premeditation - a conscious intent to kill, prior to the act 

(b) Deliberation - a killing not committed on impulse 

Under section 231 (5), murder is first-degree when it is committed during the course of accompanying enumerate offenses meaning other unlawful acts leading up to the murder. In this case, the murder occurred following kidnapping, unlawful confinement, poisoning through fentanyl injections, and aggravated assault.  

General Tips for Mooting! 

Speaking and Answering Questions 

Public speaking is a huge factor in scoring high and advancing through the rounds. It is important to present confidently and speak with power in your voice. The judges can sense nerves from a speaker. Take a deep breath and get in the right head space before your submissions. A big tell tale sign of nervousness is fast speaking. Be mindful to speak with a steady pace throughout your submission. This way, when you are asked a question, you can take your time answering, as you were already speaking at a steady pace, it is less obvious when you take a second to answer. 

Ensure you are responding directly to the question asked and not just continuing with your submission. They will notice and that is not what they are looking for. 

When answering questions from the judge, they actually don’t always expect you to answer right away. Instead of scrambling and stuttering, I learned that it's better to say, “your honor, may I have a brief indulgence to collect my thoughts”. They almost always grant you that time, a brief 10 seconds, giving you time to think, structure your argument, then respond. The real lawyer that judged me, Holly, said that people actually use this method in real court rooms as well.  

Emphasizing important words 

When doing your submission, it is important to place the correct emphasis on certain words to really get your point across. To help me remember the exact words, I bold them in my notes, and emphasize them when rehearsing. 

What I Learned

1. Know the facts of any case you cite 

If you mention any case law (provided in the factum or elsewhere), to support your argument with case precedence, or to state a quote from a justice, it is important to briefly state the context of the case and why it is significant to your argument. 

My submission originally stated a legal principle from case law like this: “Justice Simmons stated, in R. v. Ally, that courts should refrain from concluding that planning and deliberation are evident solely based on an inference of intent to kill”. 

After taking family lawyer, Holly’s advice, I changed my citing of case law to begin like this: “In R. v. Ally, a comparable case regarding guilt based on uttered threats, Justice Simmons held that the evidence of prior threats is not enough to support a finding of premeditation. I then went on to use my original quote. This new introduction into my point, gives greater context and clarity to my argument, strengthening my overall submission. 

2. Actually responding as the respondent 

When arguing on the side of the respondent, it is critical to listen to the appellant speeches, identify flaws in their arguments, and respond to them in your own submissions. When I argued the side of the respondent, I looked for key errors in the appellants’ submission and responded to it as a header to one of my main arguments. Note: for proper moot etiquette, it is important to refer to your opponents as “friends”, in order to be respectful and not sound like you are targeting them personally. 

For example, in my second round (day one), my opponent, the appellant, stated that “the murder of Nature Dupperon was committed without the requisite planning for a first degree murder conviction, that it was done “in the heat of the moment”. 

My response: [Respectfully, Justice, I disagree with our friend’s statement that the murder of Nature Dupperon was committed without the requisite planning for a first degree murder conviction, that it was done, to use their words, “in the heat of the moment”]. I then continued into my submission… 

I said: “Simply having the when, where, and how of the act undetermined beforehand does not equate to the lack of planning. As the Court of Appeal corrected, the fact that the group discussed what to do with the body, before the killing even occurred, clearly shows their

intention that there would be a body to dispose of. This discussion, in of itself, constituted planning.” 

Another example, in my fourth round (day one), the appellant stated that “the act of planning could not be determined through a person’s thoughts alone”. 

My response: “Respectfully, your honour, I disagree with our friend’s statement that planning could not be determined through a person’s thoughts alone”. I then continued into my core arguments… 

I continued with my submission: “What’s required under first-degree murder, is the goal of the act - the intention to kill”. I then followed up further using legal principles from case law (R. v. Droste and R. v. Wallen). 

Another example, in my sixth round (semi-final; day two), I was submitting as the respondent and I noted that the appellant team said “the Court of Appeal did not show deference to the trial judge's facts”. 

I then inserted into my road map: “Contrary to our friend’s statement, that the Court of Appeal did not show deference to the trial facts, we submit that the Crown did consider the trial judge’s reasoning, however, the trial judge made two substantial legal errors, rendering their reasoning fundamentally flawed”. I then continued by stating the two legal errors that the trial judge made that my partner and I will be submitting. 

This type of respondent submission is preferable to the judges because the real life role of the respondent is to respond to the specific arguments made by the appellants. 

3. Correct use of right of reply: 

This opportunity is granted to the appellant team (who always speaks first) to exercise an optional 2 minute right of reply after the respondent has made all submissions. This is specifically intended solely to address or correct specific rebuttals, not to introduce new arguments. Before this competition, I did not exactly know the correct use for the right of reply. During the quarter finals, I was the appellant, and the judges said in my feedback that there was an error made in the respondents’ submission that I should have brought up in the right of reply to support my case. In the respondent submission, they were discussing why Mr. Underwood

should be convicted of first-degree, rather than second-degree murder. The judge asked the speaking respondent if there was any case law on second-degree murder. She responded with a firm “no, there is no case law on second-degree murder.” In my feedback, this is where the judge said I should have exercised my right of reply since this is obviously incorrect; there is extensive case law regarding second-degree murder. I had mentioned in my submission case law regarding second-degree murder and it would have been important to correct the respondents on this error to get the upper hand. Next time I play the role of the appellant, I will look out for such errors and know exactly how to respond to them! 

4. Importance of precise wording 

Be VERY intentional with absolutely each and EVERY WORD you use. Say EXACTLY what you mean. My biggest mistake in the final round was accidentally contradicting myself based on the exact wording I was using. I was arguing for the appellant side, submitting that Mr. Underwood did not meet the criteria for planning under section 231 (2) of the Criminal Code, and, therefore, could not be found guilty of first-degree murder. 

Somewhere throughout my submission, I stated: “Pursuant to section 231 (2) of the Criminal Code, a “planned” murder must entail a “calculated scheme” in which each step was “conceived and carefully thought out”. A few sentences later, I stated: “the evidence demonstrates that the group had been planning as they go, rather than executing a prearranged, calculated scheme”. This is where the judge had interrupted me saying, “so it was planned to some degree. I then realized I had unintentionally contradicted my argument through simple wording and it was hard to get out of that hole, although I did my absolute best to save it. What would have been better to say in that sentence was that the group had been “improvising the crime and reacting as they go”. It essentially says the same thing, without the risk of contradiction. This may have been a core reason why we lost points in the finale, leading to our loss, however, this is a lesson I am so grateful to have learned and will not repeat in future submissions. To my surprise, having used that submission in 3 rounds, prior to the finals, no judge had caught that. Making it to the highest level, submitting to 7 judges (professors and lawyers), is the highest level of scrutiny that your submission will ever receive. 

My Main Message! 

What I believe helped me advance so far was the essential combination of a good partner, good public speaking, and a whole lot of confidence. Advancing all the way to the finale, as a first and second time mooter, I hope will give more students hope that they CAN do it, regardless of

whether or not they have past mooting experience. Overall, this was an absolutely surreal experience where I deepened my passion for public speaking and fell even more in love with the field of law! I hope mooting can do the same for you!