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Do you think a chapter would ever go down the path of loaning there company's greatest warrior to the Deathwatch?

Well the Deathwatch need chaplains for spiritual guidance just like any other marines, It would depend on how zealous the chapter was if they would send their best one I suppose.

Chapters are willing to second the rest of a Company's command staff to the Deathwatch, so I don't see why not.

Turns out even if the chapter did loan out there company's champion, upon arriving at the Deathwatch HQ, his title\rank wouldn't matter, it's effectively stripped. He would just be a plain kill team member. It's all good tho because Deathwatch do actually have there own champions.

Going by the Deathwatch RPG they do have champions among their number.

I'd say it's more likely the Company Champion served in the Death Watch before that, but sending him anyway isn't totally odd. He's a great warrior but the Chapter works perfectly well without him.

Judging by the Kill Team Cassius set, the Dark Angel actually is a Champion.

Zameon Gydrael, Company Champion
https://www.games-workshop.com/resources/catalog/product/threeSixty/60010699004_DeathWatchZameonGydrael360/01-01.jpg

Mind, he uses a plasma pistol instead of his bolt pistol and combat shield, but he's a Dark Angel- of course he does. Looks like he brought his own sword, though!

It has also just come to my attention that yonder Kill Team Cassius is actually the unique marine components of the boxed game Deathwatch Overkill. Perhaps if you can find someone with a copy, there may be a section in the lore there about that character, as well.

Cart before the horse. Chapters don't send their Company Champions, they send other promising members who become badass enough to be Champions during their time in the Deathwatch.

I mean, literal link to a Dark Angel company champion DW kill-team member.
I just figured being in a boxed game he might have more lore, and indeed via Lexicanum

Zameon Gydrael is a member of the Deathwatch. Hailing from the Dark Angels Chapter where he was a Company Champion, he is one of the oldest and most experienced members of the Deathwatch.

This quote is from White Dwarf 109 (Feb 2016) of the new serial system, with the release of DW: Overkill the boxed game.
I couldn't guess how often the practice is though. However, for many chapters, the company champion isn't a permanent position. Perhaps yearly or at least periodically, they choose a new champion via some method. I'm sure after a stint as champion, the veteran would be more likely to fight as Vanguard than Sternguard with their experience in single combat. It just says he was a champion, not necessarily that he was one when he joined the Deathwatch. The Dark Angels for example, though it differs by the company, select a winner from various contests, mental fortitude, duelling competitions and the like. For the Blood Angels, Company Champions fight to claim or defend their title on feast days. Its a title of honour to be won and defended, rather than promotion in the hierarchy of the Chapter usually, so being an ex-champion is entirely possible. Hence his plasma pistol instead of carrying the ceremonial combat shield and bolt pistol, he could actualy just be a company veteran at his formal induction to the DW having been replaced by another Champion.