Is the tree of the field a man?

Question

Dvarim 20:19 reads:

כִּי תָצוּר אֶל עִיר יָמִים רַבִּים לְהִלָּחֵם עָלֶיהָ לְתָפְשָׂהּ לֹא תַשְׁחִית אֶת עֵצָהּ לִנְדֹּחַ עָלָיו גַּרְזֶן כִּי מִמֶּנּוּ
תֹאכֵל וְאֹתוֹ לֹא תִכְרֹת כִּי הָאָדָם עֵץ הַשָּׂדֶה לָבֹא מִפָּנֶיךָ בַּמָּצוֹר

When you besiege a city for many days to wage war against it to capture it, you shall not destroy its trees by wielding an ax against them, for you may eat from them, but you shall not cut them down. Is the tree of the field a man, to go into the siege before you?

Rashi explains that the word 'Ki' denotes a (rhetorical) question not a statement:

Is the tree of the field a man, to go into the siege before you]?: The word כִּי here means“perhaps:” Is the tree of the field perhaps a man who is to go into the siege by you, that it should be punished by the suffering of hunger and thirst like the people of the city? Why should you destroy it?

So the Torah is saying: Is a tree like a man? No!

If so, why do we find that many commentaries try to find connections between man and trees?

Answer 1

Rashi's understanding is only one, as Michoel said, of the "70 faces of Torah". The syntax of this pasuq is inherently ambiguous, and it is not clear whether the correct reading of the verse is as a rhetorical question or a statement. Ibn Ezra explains that the Torah is in fact equating people and trees:

ולפי דעתי: שאין לנו צורך לכל זה וזה פירושו כי ממנו תאכל ואותו לא תכרות, כי האדם עץ השדה. והטעם: כי חיי בן אדם הוא עץ השדה

In my opinion, we don't need these or those [erroneous explanations of other commentators]. Rather, the [correct] explanation is, "For you should eat from it, and not destroy it, because [as] a person is the tree of the field." Meaning, the lives of people are [as] trees of the field.

Regardless of which explanation holds more ground grammatically, the point remains: throughout TaNaKh, trees are powerful metaphors for righteous people, happiness, stability, and the Torah itself. As Shalom wrote, poetic/midrashic license allows us to read this (admittedly ambiguously phrased) pasuq in a way to derive meaning. See, for examples, some of the sources that Jeff Spitzer brings in his article here, including the Tzena uRena and the MaHaRaL of Prague.

Answer 2

The simple reading of the verse is, as you stated, the Torah is saying "no it's not, so don't attack the trees."

But because the Torah chose to word it in such a fashion, the commentaries saw that as poetic license to draw similarities between humans and trees. (But not in such a way as to violate the halachic interpretation of the verse, namely, don't cut down fruit trees when laying siege to a city.)