Expression: "He would never have a deal causing him loss."

[Tom]

Hi

Is the following sentence correct and natural?

[Yankee]

.
That sounds a little odd to me, Tom. What's the context?
.
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"Nearly all men can stand adversity, but if you want to test a man's character, give him power." ~ Abraham Lincoln

[Alan]

Hi Tom,

Your sentence is a bit too 'condensed' to sound natural to me:

[Molly]

? He would never be involved in an unprofitable deal.