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[Tusky]

I am about to take the elm of a ship - the good ship SS. Winning

[Jubal]

Take care that my next win doesn't leave you stranded on the beech, then.

[Tusky]

oak k

[Jubal]

And I'll have another win, if I may(ple)

[Tusky]

I just won so hard it made me sick(amore)

[Jubal]

I didn't realise the experience would overwh(elm) you that much

Win!

[Tusky]

I wish to con(i)fer my sincerest congratulations to you for that win, there.

[Jubal]

Okay, I'm not sure I can teak many more of these tree winning puns.

[Tusky]

Maybe it's time to bid them a cherry-o

[Jubal]

I guess we'll have to see what root this thread goes in next if we branch off in another direction.

[Tusky]

I do not have a dog, but am aware that they sometimes bark

[Jubal]

Well, let us avoid the cat-astrophe of running out of tree words and instead segue to animal puns!

Win(telope)

[Tusky]

victree! (frog)

[Jubal]

Vic-uña-tory!

[Tusky]

M-win-k