Jetpack Publicize Tweet with image - wordpress

I currently have Jetpack's Publicize working nicely with my WordPress posts and Twitter. I even filtered the Open Graph tags to enable Twitter Cards and they work perfectly.
I'm trying to ensure that each Tweet also appears with an image in Twitter feeds. Currently, the only way to view the image associated with my Tweet is by clicking or tapping the Tweet and viewing its Twitter Card image.
My posts currently appear in Twitter feeds like this:
But I would like them to appear like this:
I've searched the limited Publicize documentation to no avail and I would really appreciate anyone's insight on this.
Is it even possible? Do I need to choose between displaying a feed image and a Twitter Card?
Thanks!

According to a Twitter employee:
The last URL in a tweet will be taken as "precidence" [sic] for
whether to show an image (pic.twitter) or a card (via a tweeted URL).
Source: https://dev.twitter.com/discussions/23575#comment-66500

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