1. The Parshah begins with Yaakov sending מלאכים to Eisav. Rashi explains on the words וישלח יעקב מלאכים that they were מלאכים ממש, to tell us they were angles and not human messengers. However, if the word מלאך also means messenger (being the word “angel” comes from the Greek word “angelos” which means messenger), then how does saying מלאכים ממש tell us they were angels, if it just translates as real ממש)) messengers? Why is it that we call angels מלאכים if really it means messengers? It’s because a real messenger is someone that identifies with the message and therefore angels are the quintessential messengers because they have no identity of their own, rather they identify solely by their mission. That’s the reason why מלאכים can’t multitask because they are completely absorbed and identify with the task at hand. Therefore, by saying מלאכים ממש-real messengers, it’s saying that they were actually angels and not human messengers because ממש messengers refers to angels who are the prototypical messengers. In the הקדמה to the ספר המקנה, he explains the Pasuk כי שפתי כהן ישמרו דעת ותורה יבקשו מפיהו כי מלאך ה' צבאות הוא (end of Haftarah Parshas Toldos). Why is it that a person should seek out a Rebbi who is דומה to a מלאך? As mentioned, a מלאך has no identity of his own and is completely absorbed and identified by his mission. The ideal Rebbi is someone comparable to a מלאך in this sense that he has no ulterior motive in teaching Torah and has no self-interest rather he is only identified by and dedicated to his mission which is to teach Torah.
  2. ויירא יעקב מאד ויצר לו (לב,ח) The Pasuk says that Yaakov was very frightened and he was pained. Rashi says he was scared maybe he’ll get killed and it pained him maybe he’ll have to kill someone. The רא"ם asks why he was pained that he might have to kill someone if the הלכה is הבא להרגך השכם להרגו? The question is difficult to understand because even if it was permitted the kill, it can still be painful. He was allowed to get killed and yet he was still frightened to get killed, and the same goes for having to kill someone. Reb Simcha HaKohen Sheps, a Rosh Yeshiva from Torah Vodaas, said over a story with the Brisker Rav that his wife, the Brisker Rebbetzin, had twin girls and they died on Friday night. When he came to their house Friday night, they told him not to come inside because he was a Kohen. When he returned on motsei shabbo, he saw Reb Berel and Reb Dovid carrying out the נפלים and they were crying. The Brisker Rav told them that the Rambam says אין מתאבלין עליהם so no crying. We see that a person’s emotions need to be completely controlled by the Halacha. Therefore the רא"ם asked on Yaakov why was he pained to have to kill someone if it’s a דין that is מותר. The דעת זקנים בעלי התוספות explain that he was ויצר on the fact that he was scared of עשו after Hashem had promised him that everything will be fine.
  3. ויצו אתם לאמר כה תאמרון לאדני לעשו (לב,ה) Some of the words in the Pasuk are seemingly unnecessary. Once Yaakov says לאמר, he doesn’t need to say כה תאמרון and once it says כה תאמרון, there is no need for the לאמר? Yaakov instructed the מלאכים to say עם לבן גרתי. Rashi says גרתי בגימטריא תרי"ג, כלומר עם לבן הרשע גרתי ותרי"ג מצות שמרתי ולא למדתי ממעשיו הרעים. The only way for Eisav to have understood the message of Yaakov saying תריג מצות שמרתי was if this message of the מלאכים was said בלשון הקודש. How did the מלאכים know to say this message in לשון הקודש? The Gemara in סוטה לח ע"ב says that anytime it uses the לשון of כה, it indicates that it needs to be said in לשון הקודש, as it says כה תברכו by ברכת כהנים. Therefore, it was necessary for it to say כה תאמרון as well in order for the מלאכים to know that they were to say the message from Yaakov in לשון הקודש in order for Eisav to realize that גרתי is תרי"ג.
  4. Rashi brings two explanations on the word גרתי. The first explanation is that Yaakov was saying to Eisav that it’s not כדאי to hate me because I’m only a גר and the ברכות of הוה גביר לאחיך were not מתקיים. The second explanation is גרתי בגימטריא תרי"ג that I lived with לבן and I still kept all the מצות. But why would עשו care if Yaakov kept the תרי"ג מצות or not to the point where Yaakov felt the need to tell him this information? To answer this question, both these explanations should be read together. The Brachos of Yitzchak were on condition that only if Yaakov keeps the Mitzvos would the Brachos be fulfilled. Therefore, by saying not to hate me because the Brachos were not fulfilled doesn’t mean anything because maybe he didn’t fulfil the conditions. Therefore, the second reason is needed to say that I did keep the Mitzvos and still the Brachos were not fulfilled and therefore there is no reason to hate me. The second explanation is needed to explain the first explanation. Therefore, Yaakov needed to tell Eisav that he kept the תרי"ג מצות in order for the first explanation, that the Brachos were not fulfilled, to be even though he fulfilled the specific conditions.
  5. Rebbetzin Kreindel, the wife of the שו"ת זכר יהוסף and sister of ר' ישעיה (פיק) ברלין would say that it says הוה גביר לאחיך, שהרי לא נתקיימה בי. If you take out the בי, the ב and י from גביר, you are left with גר. The Brachos were not מתקיים בי because Yaakov was only a גר.
  6. ויאבק איש עמו עד עלות השחר (לב,כה)
    Yaakov fought with the שרו של עשו who is the יצר הרע. What did the מלאך appear like to Yaakov? The Gemara in Chullin 91a brings a מחלוקת. One opinion says כעובד כוכבים נדמה לו and according to the other opinion כת"ח נדמה לו. Similarly, the Gemara in Sukkah that says when a תלמיד חכם dies, the יצר הרע appears to him כהר but to a רשע, it appears to him כחוט השערה. Either way, it seems that there is no defined appearance and it appears as an illusion differently to different people. The reason is because the יצר הרע really has not מציאות and it’s only נדמה. The יצר הרע is only a דמיון that takes on the form of whatever it needs to be in order to distract a person. The מהר"ל in נתיב היצר discusses the Gemara in Kiddushin that says the יצר הרע is מתחדש בכל יום because something that is of מציאות today looks like it did yesterday. But something of no מציאות that is only דמיון looks like something new and different every day. This is why when Yaakov asks what his name is, he says why are you asking my name because a name is only by something that is defined as opposed to something that cannot be defined because it has no מציאות or identity. This is the meaning of what Yaakov said when the Pasuk says ויקרא יעקב שם המקום פניאל כי ראיתי אלהים פנים אל פנים. Because really the יצר הרע only exists for us to defeat him. Therefore, when a person sees through him, he is really seeing the face of Hashem because the יצר הרע is a representation of Hashem, creating obstacles which gives him the challenges which can be overcome, which gives him the opportunity for growth. Therefore when you see through the obstacles, you see it as the hand of Hashem. When Yaakov says כי ראיתי אלהים פנים אל פנים, he is saying that when he sees the true meaning of the יצר הרע, he is really seeing a מציאות of קדושה.
    The Gemara in Pesachim 22a says אין בגידין נותן טעם and the גיד הנשה is just עץ בעלמא yet the Torah prohibits us to eat it. This is the same idea of the יצר הרע that there is really nothing to it and its all דמיון.
    But how can the יצר הרע appearing like a ת"ח be bad? The Medrash in Breishis on the Pasuk וירא אלוקים את כל אשר עשה והנה טוב מאוד וכו' says that טוב is the יצר טוב and מאוד is the יצר הרע. In addition, it says טוב זה החיים ומאוד זה המות. How is that we see the יצר הרע from the word מאוד and how could מואד be מות? The answer is that too much good is bad. If a person tries and thinks he can be perfect, he will not succeed and he will get depressed and down about himself because it is humanely perfect to be imperfectly human. The יצר הרע can appear to someone looking like a ת"ח saying you have to be perfect like this and if you don’t, you are a failure and a nothing. But a person must remember that he is not supposed to be like that ת"ח nor can he be like such a person, but rather he is to be the best person he could be with the skills and talents that Hashem gave him. In Judaism, it’s not all or nothing. Most of the human progress takes place in the gray area between all or nothing. But is the message of the גיד הנשה negative, that unfortunately Yaakov was attacked and he limps or is it a positive message of hope? From the חינוך and other ראשונים, it’s clear that it’s a positive message. The idea is that even though Yaakov was attacked and injured, he persevered and continued to walk on. To be able to walk even when your צולע על ירכו, when you can’t be the perfect image of the ת"ח, that is the real challenge and only if a person continues onward will he reach where he needs to get. This is really the story of the Jewish people that even though we are hated and attacked, we don’t give up and throw in the towel, rather we continue on pushing through.
  7. ויפל על צוארו וישקהו ויבכו (לג,ד) The Rav said the following vort from his father. Rashi explains why there are נקודות on the word וישקהו. The first opinion is שלא נשקו בכל לבו. The second opinion of רשב"י is הלכה היא בידוע שעשו שונא ליעקב, אלא שנכמרו רחמיו באותה שעה ונשקו בכל לבו. The first explanation makes sense that the dots are coming to minimize that usually when it says וישקהו, it is wholeheartedly so comes the dots to tell us that he was not נשקו בכל לבו. But according to the second explanation that it was a real נשיקה, how do the dots reduce and takedown from the simple meaning of the Pasuk?
    The רשב"י says that הלכה היא בידוע שעשו שונא ליעקב. Therefore, when it says וישקהו, the simple reading of Pasuk is that it was a fake kissing and the dots come to tell us that it was a real kissing. But it’s reducing the meaning because a “real” kissing for עשו who is שונא ליעקב is that he doesn’t really mean it, and therefore if he does mean it in this context, its degrading and reducing him in the sense that he can’t stick to his שיטה that עשו שונא ליעקב. If one holds of the ideology of עשו שונא ליעקב but if he loses himself in a weak moment and is overcome by emotions and is נשקו בכל לבו, that shows that he is inconsistent and that’s the גנאיthat עשו can’t stick to his own ideology. (על דרך צחות, the velt says this is why חסידי אומות העולם are called חסידים because they don’t keep הלכה).
  8. In the Haftarah, the Pasuk says מחמס אחיך יעקב תכסך בושה (עובדיה א,י. Most Rishonim learn that it’s referring to the חמס that Eisav did to Yaakov that he should be embarrassed about. But in the שערי תשובה או"ח ס' תפב, he quotes הרב מאיר ערמאה (son of the עקידת יצחק) explaining the above Pasuk that Eisav should be embarrassed that Yaakov had to come with trickery, which looked like חמס, in order to get the Brachos. Eisav should be embarrassed about this that Yaakov went through all this effort to attain חיי עולם and Eisav who had greatness disregarded it and opted for רע. The Pasuk is referring to the חמס done by Yaakov from Eisav and the בושה is that Eisav had it all and didn’t appreciate its importance and therefore gave it up, while Yaakov who initially didn’t have it strived for it.
  9. ותמנע היתה פילגש לאליפז בן עשו ותלד לאליפז את עמלק (לו,יב)
    Rashi says להודיע גדולתו של אברהם כמה היו תאבים לידבק בזרעו. תמנע wanted to be the פלגש of Avraham but he rejected her so she went to אליפז in order to be דבק בזרעו. One could have said that Avraham was justified in his decision to reject תמנע because after all, עמלק ended up coming from her. But the Gemara says that there was a טענה on Avraham for not marrying her because maybe had he married her, עמלק would not have been born. The same idea is found by דינה that Yaakov was punished for hiding her from Eisav because maybe had they gotten married, she would have turned him around. The message is that we cannot prove anything from History because perhaps history would have been different had they acted differently. Of course, the Gedolim of each generation make decisions based on the information they have in front of them, but one can’t point to a moment in history and say they were right in how they acted based on what ended up happening because who knows what could have been had they acted differently.
    The same idea can be found in the Kuzari in מאמר שני סעיף כד. He discusses the reason why בית שני did not become a גאולה שלימה, and there was no השראת השכינה and ארון, was because most of the תלמידי חכמים did not come up with Ezra and they remained in בבל. The people that went up with the Ezra, the עשרה יוחסין were from the lower end of the Jews and those that remained in Bavel were כסולת נקיה because they were the purest of Jews and Ezra brought up the intermarried Jews. After the חורבן, the Gedolim in Bavel could have said to themselves that they were right to not go up but rather to stay in Bavel because, in the end, nothing came of it. But the Kuzari is pointing out that it’s really the opposite of what we should think that really had they gone up, it would have been a different story and the fact that it only became what it became was because they didn’t go up. This is another prime example that you can’t prove anything from history.