English Translation
My father took out a lot of money.
Isn’t this more like “My father sent me a lot of money”? I think くれた implies it took out/sent money on my behalf.
The English-Japanese pair doesn’t match.
くれた, however, means “to do for someone’s sake”. お金を出してくれた in this sentence doesn’t mean “to send me money”, but “to pay/invest on my behalf”. – i.e. I did not receive money directly from my father. My father 1) paid money to the third party; or 2) invested into a project/organization that I was involved.
Give the たくさんの + お金 collocation, I interpreted the sentence as the second meaning. We have a specific phrase 出資する（しゅっしする）= 出す + 資本（しほん; capital）.
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Thank you @MsFixer, that is very helpful.
So, I noticed the くれた and took it to mean “for me/on my behalf”; my dictionary says that one of 出す meaning is also “to send”, so I kind of thought that could be the meaning, but what you said maid it clear that choice would not be appropriate in this case.
So maybe it is better to think about the basic meaning of the verb (to take out, or to put out), and how it could be used metaphorically.
So in this case, it looks like dad had to spend a lot of money for me, even though no dictionary would list that meaning.
I think the “on my behalf” part would be important to underline, however…
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Yes, “on my behalf” is the important part, indeed.
出す is a simple common word that can be used in a variety of situations. Such a simple one is often a tricky one as well.
Your dictionary says that one of the meanings is “to send”. That is correct. Here are examples:
Tom wrote a letter to Mary. = Tom wrote a letter and sent it to Mary. = トムはメアリ―に手紙を出した。(Note: we don’t say トムは手紙を書いてメアリ―に出した。It’s super redundant. You had better drop 書いて.)
Mary said to Tom: “Bring the garbage to the garbage pickup site.” = メアリ―はトムに「ゴミを出して」と言った。
I need to submit this application by tomorrow. = この申請書を明日までに出さないといけない。(Note: 出す is interchangeable with 提出する（ていしゅつする）)
The image of 出す in these three sentences is “to release something from the initial position to somewhere else”. That’s why 出す can be “to send”, or “to take something out”.
お金を出す literally means “to take out one’s money out of his pocket” (i.e. the initial location of his money was in his wallet or bank account, and he releases it). We also have similar expressions: お金を使う（つかう）and お金を費やす（ついやす）. お金を使う (to use) and 費やす (to spend) are more frequently used for one’s own use whereas お金を出す is to pay/invest for someone else’s benefit.
The original Japanese sentence “私の父がたくさんのお金を出してくれた” can be replaced with “私の父がたくさんのお金を出した” (i.e. drop くれた). Both of them mean “my father paid/invested on my behalf”. Conjugating くれた with the verb 出す, the speaker (I) expresses her appreciation. Dropping くれた makes the nuance vague – the speaker might or might not want her father to pay/invest money, and keep him out of the loop.
Hope this helps 
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