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In the movie The Thomas Crown Affair there is the following dialog:

I'm just an amateur.
Beginner's luck, huh? Gentleman jockey wins the Derby.
Something like that.

The expression "Gentleman jockey" is not available in the more common online dictionaries, so
what does "Gentleman jockey wins the Derby" mean here and in what contexts could I use it?

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    Please include the research you've done, or consider if your question suits our English Language Learners site better. Questions that can be answered using commonly-available references are off-topic.
    – NVZ ♦
    May 21, 2017 at 16:53
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    @Josh I found the definition instantly on Google, the same one you posted, and other.
    – NVZ ♦
    May 21, 2017 at 16:59
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    @Josh Sure, they may ask. But they could also include the research that they have done. :)
    – NVZ ♦
    May 21, 2017 at 17:01
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    @NVZ Anything, anything can be found on Google. The fact that an answer can be put together from info on Google is not enough to make it answerable using "commonly available references." In this case, yes, a quick Google yields the answer, and the question showed zero research, which is why I posted a comment rather than an answer.
    – ab2
    May 21, 2017 at 17:03
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    The expression "I'm just an amateur" is also absent from dictionaries. That's because is this not an idiomatic expression. It is a sentence, and one that means just exactly what all its individual pieces mean separately. You have to look up its pieces. This is not a candidate for reopening.
    – tchrist ♦
    May 21, 2017 at 21:22

2 Answers 2

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Gentleman Jockey is an expression that refers to:

  • Amateur rider, generally in steeplechases.

By extension it is used to refer to someone who is not a professional player but may happen to be a winner despite their inexperience.

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  • thanks for your answer, I certainly googled before asking here. But I got no results for the whole phrase and didn't think of asking for part of the phrase.
    – Max Koretskyi
    May 21, 2017 at 17:31
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    @Maximus - you are welcome, preliminary research is considered essential in this site, so next time please remember to mention it.
    – user66974
    May 21, 2017 at 17:36
  • will do, good luck)
    – Max Koretskyi
    May 21, 2017 at 17:44
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    In this case Gentleman also implies upper class as used to happen in cricket
    – Neuromancer
    May 21, 2017 at 22:20
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The term gentleman jockey can be used as a derogatory term for a member of the upper class dabbling in the sport - a dilettante with no real skills.

An excellent description can be found in the January 1848 issue of The Sportsman:

Critics will tell us that at the amateur performance, Mr. So-and-so, or Lord Such-a-one, played Charles Surface or Sir George Airy, very well--for a gentleman. Even in our own line, where a gentleman is declared to be nothing and nobody without his recreations, he still plays but second fiddle at them. A gentleman huntsman, nine times in ten, is taken but as another term for a bad one; and a gentleman jockey generally unites the two on much the same understanding. At most he may reach in this sphere the acme allowed by Mr. Scrope Davies, who, in speaking of a friend’s great efforts to carry out the character in every perticular, admitted “he did look and ride like a jockey, but then it was like a bad jockey."

The Sportsman, January 1848, p. 343

I could not find any occurrences of the phrase gentleman jockey wins the Derby other than the dialog mentioned in the OP. But based on the above I would interpret it as an affirmation and rephrase of the preceding sentence:

01:14:56 I'm just an amateur.
01:14:59 Beginner's luck, huh?
01:15:02 Gentleman jockey wins the Derby.
01:15:05 Something like that.
link

In other words, my success is due to an unlikely stroke of luck, similar to an amateur (an inept one) winning a professional competition.

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