"We won that battle thanks to Jane Canary," said no one. Ever.
I have seven pirates across two accounts who are at the highest possible level, and I don't remember Eagle Shades being this difficult to defeat during the Contest of Champions. Even if my pirate and all companions gang up and attack (and hit) only one character at a time, their health is so high it would take multiple rounds to defeat them. Which wouldn't be a problem except they are able to heal themselves numerously, and with a suspiciously high amount of health in between the rounds. And since the drop rate is so overwhelmingly low (potentially upwards of six lengthy battles), its more weathering hits with your tank companions than any real strategy.
Which brings me to my point. The absolute best thing that happens is Jane Canary being defeated - because let's face it, she's completely fucking useless. But because the Contest of Champions is a promotion quest, they resurrect her dumb ass each round and force me to use her in a crippled state further stacking the deck against my poor crew.