Rabbi David Cooper

The Angel of Death is a messenger of God. It has been associated with the dark angel Samael, who represents Satan, but acts only under the direction or approval of God.
Many stories describe the battle between the Angel of Death and humans. This angel sometimes must resort to deception, for it is not all powerful. Indeed, occasionally Death is defeated.
King David once asked God when he would die. God responded that no person would ever know in advance the time of their death.115 But because of David's merit, he learned that he would die on a Sabbath day when he was seventy years old.

So David spent every Sabbath day exclusively in the study of Torah, for it is said that the Angel of Death has no power over anyone fulfilling one of the commandments. One Sabbath day, which was also the holy day of Shavuot, David heard a strange, wondrous sound in his garden. He went to see what was making the noise and the steps leading to the garden collapsed, killing him. The Angel of Death had caused such an alluring noise, David forgot that death was near.116 The Angel of Death has many tricks up its sleeve.
On the other hand, when the sage Rabbi Joshua ben Levi was about to die, the Angel of Death was directed to carry out one of his wishes. The scholar asked Death to show him what it looked like where he was going, which the angel agreed to do. But before departing, Rabbi Joshua said, "Give me your knife [that which you use to kill people], lest I be frightened along the way." This is how Rabbi Joshua got the Angel of Death to hand over to him the instrument of death.117
When they arrived at Paradise, Rabbi Joshua jumped over the wall, thereby entering without first dying! The Angel of Death grabbed the corner of his garment, but Rabbi Joshua swore that he would not return to his earthly life (only to await death).
The Holy One had to intervene, saying that Rabbi Joshua's oath not to return to life would only be valid if in his entire life he never made an oath that had to be annulled. This of course is almost impossible for we are always making casual oaths, like promising ourselves that we are going to do something that we never do, or, conversely, swearing that we will never do a thing again, and then do it anyway. It is the reason Jews say the kol nidre prayer at the time of Yom Kippur, so that unintentional vows and unfulfilled oaths are not held against someone. But in the life of Rabbi Joshua, he had never said or thought anything that he did not fulfill. So his vow not to return back to life was honored.
The Angel of Death pleaded with him. "You must return my knife!" For without this knife, nobody would ever die again. Rabbi Joshua refused to return the instrument of death. It was a standoff, and the entire universe held its breath.
Finally, a bat kol (a heavenly voice) boomed out: "Return it to him, for mortal creatures require it!" Thus death was reestablished. What would the universe look like if "mortals" ceased to die? After this, the Angel of Death was never again misled into giving away its knife, even though another sage tried the same maneuver.118

So Rabbi Joshua tricked Death and entered Paradise without dying. Ten others are said to have entered Paradise "alive," the best known of whom are: Elijah the prophet; Hanoch, the father of Methuselah; Serah, the daughter of Asher; and Bithiah the daughter of Pharaoh (who was given this reward for having saved Moses).119
Kabbalah adds another dimension to death, suggesting that it is not monolithic but has a number of levels. It says that the Angel of Death is protected and "ridden" by the Shadow of Death. Although they have different energies, they are inseparable partners. Moreover they have different gateways into the realm of death, for there are "gates of death" and "gates of the shadow of death." Indeed, it is said that there are innumerable, mysterious passageways to death "hidden away from humankind, who know them not."120
Death, therefore, is far more complex than simply a realm of non-living. The actual dying process, the transition, the time immediately after death, the entire first year following one's death each have unique qualities. All along the way, those who are living can serve, support, and be advocates for those who are dying or who have entered the death realms. Many people feel helpless in the face of death, but the truth is that by understanding the many facets of death and dying, we come to realize that there is a great deal we can do.

THE DEATHS OF SAGES
The Talmud records a number of deaths in which sages return in dreams to describe the dying experience. In one story, Rava was attending his dying friend Rabbi Nachman. Nachman asked Rava to intervene with the Angel of Death, to use his influence so that Death would not torment Nachman. Rava was surprised by this and asked Nachman why he did not make the request himself of the Angel of Death, for Nachman was highly reputed and had great merit. Nachman replied that when the Angel of Death has been instructed to end somebody's life, that person no longer has any influence.

The story continues. Rava asked Nachman to return in a dream after his death to describe what dying was like. Indeed, Nachman did return in a dream. "Did you suffer pain?" Rava asked. Nachman responded, "[Death was like] the taking of a hair from milk." He added, however, "If the Holy One told me to go back into the world, I would rather not for the fear of death is too great."121 Despite his advanced awareness, Nachman was still deeply afraid of the possibility of a painful death.
This story teaches many things. People with merit can influence the Angel of Death, except when they themselves are about to die. This influence can be used to ease suffering for those in the dying process. Normally, this is done through prayer, which is the primary tool used to reach angels and Death. Additionally, the story teaches that we can communicate with other realms through dreams. Nachman tells us from the other side that his experience of death was quite easy. Nonetheless, the fear of death far exceeds the experience, so much so that Nachman did not want to return to go through it again, even though the actual experience for him was as simple as taking a strand of hair out of milk.
In another talmudic story, when Rava himself was dying, he was attended by his brother, Rabbi Se'orim. As in the previous story, Rava asked his brother to tell the Angel of Death not to torment him. His brother asked him, "Are you not his intimate friend?" Rava's response was, "Since my mazzal [fate] has been delivered to him, he does not pay attention to me."
In this story as well, Rabbi Se'orim asked his brother to return in a dream after his death to describe what dying was like. Rava did so. When asked if he suffered, he replied, "As from the prick of a cupping instrument."122
Cupping is an ancient technique in which glass spheres are heated and then placed on a person's skin. As the cup cools, a vacuum forms inside and the skin is drawn up by suction. Ostensibly the process draws toxins from the body, through the skin. The Chinese use this method today and I have experienced it. The sensation is unusual, but not uncomfortable. In fact, the pulling of a bandage off skin is far more irritating.
So the sages are clearly informing us that the dying experience is altogether tolerable, but that the potential for being tormented in the dying process is unbounded. No matter what our station in life, how many good deeds we have done, how pious a life we have lived, the Angel of Death does as it wishes when taking someone to the other side. Yet, if someone has an advocate who speaks in their behalf, the dying process can go much easier. This is important information for anyone who is in a position to help a person going through this transition.
Also, the sages apparently asked others to return after death, to describe not only death itself, but what it was like in the death-realms. Dreams are usually the vehicle for this transmission between different realities.
Almost everyone dreams of close relatives who have died. These dreams are often quite vivid. Sometimes they occur soon after death and often they reoccur for months or years.
The sages trained themselves to work with dreams. We can do the same. When we are skilled in this process, we can communicate in exactly the same way these stories describe. We can ask dream images questions like: "How was death for you?" or, "What is it like where you are?"