Many people had excellent ideas on how the Owl might win the Race of Eight Winds. A number of people leaned on the Boromar Clan for assistance. Many came up with ways to turn the contestants against one another. One suggested glamerweave sashes imbued with subliminal mind control magic. It was a tough choice, but in the end our panel of judges went with the following plan, submitted by Jessica Chemise.
How will the Owl win the Race of Eight Winds? By ensuring the outcome is decided ahead of time, of course.
First, you need to identify the goal, stated and implied. That is, it is obvious that you need to win the race, but what you need to do is make everyone else come in less than first. Sometimes, it doesn’t need to be obvious. In other cases, it may need to be obvious but untraceable back to you.
Hire an experienced ranger to fly as a second. She/He is ONLY involved to take out any unexpected last minute additions to the roster, such as OTHER adventurers. Actually trying to win will negate our agreement, and the rest of the payment.
Manipulate events so that the Hawk’s rider personally owes us a favor in exchange for silence. Call it in prior to the race.
Next step: Pegasus and Hippogriff need taken out. As the fastest competitors, they are our biggest threat.
Highwater’s representative is known for its pride, and the solution is obviously to encourage the Gargoyle and Hawk to team up against it. Once they have taken out the Pegasus, then the two (presumably weakened) will be the next targets. Not from our rider, of course. From the Griffon, who sees them in their weakened state and is compelled to take at least one of them out to satisfy the fans (this is, of course, helped out by the favor we called in from the Hawk). This leaves the Griffon open to attack from the other, and taking advantage of this division allows us to swoop in and take out the weakened Griffon, no matter the outcome. The Hawk has the blackmail threat hanging over his head to keep him from passing us at this point.
At this point, two of the three ‘threats’ to our victory have been dealt with. Only the Hippogriff remains.
Have a trained poisoner coat the Glidewing’s crossbow bolts with a sleeping poison without the rider’s knowledge. Have a third party (a loyal compatriot, disguised and protected from scrying), make the glidewing rider an offer, claiming to be a speculator who has a large wager riding on the supposition of the Glidewing winging the Hippogriff’s rider. He has taken out the Hippogriff and disqualified himself for using poison (albeit unknowingly) in one fell swoop.
At this point, the owl-rider flies the length of the track, crossbow still in her belt. We are out several thousand gold…. but it isn’t about the money, or the land. it’s about the Rod of Eight Winds.
Victory.
For pure creativity, an honorable mention must go to MetaDM. Unfortunately, the question was specifically how the Owl would WIN… but bonus points for giving us a glimpse into the race!

The Owl gives it up to his toughest competitor.