WWE

A Tragedy Helped Will Ospreay Choose AEW Over WWE

Originally posted on The Sportster | By Shawn Van Horn | Last updated May 28, 2025 4:51 PM ET

After becoming one of the most celebrated wrestlers in the world with promotions like New Japan Pro Wrestling, Will Ospreay signed with AEW in November 2023. It led to a few back and forth comments between Ospreay and Triple H after WWE tried to get him to join them, but it's safe to say that Ospreay made the right decision. During his time in AEW, Ospreay has arguably become Tony Khan's most over star. He is a two-time AEW International Champion and was the favorite to win the Owen Hart Foundation Tournament, which made his loss to "Hangman" Adam Page at Double or Nothing a surprise. Despite the upset loss, don't look for Will Ospreay to regret his decision, because when he signed with AEW he was not only thinking about his wrestling career but his family, which was created amidst tragedy.

Will Ospreay's Girlfriend Is Fellow Wrestler Alex Windsor

Last August, Will Ospreay spoke about his first year in AEW with the New York Post. During the talk, he mentioned why he signed with AEW in the first place, which had everything to do with his girlfriend, fellow wrestler Alex Windsor.

They've been together for a few years now, but their relationship, while a happy one, was formed out of mutual grief. This is because Windsor was married to another wrestler named Ryan Smile, who was also Ospreay's best friend. Sadly, after just one year of marriage, Ryan Smile took his own life in 2020.

Will Ospreay Signed With AEW Because Of His Family

A few years later, Ospreay and Windsor, who were already close friends, bonded on a deeper level as they both struggled to get over losing Smile. This led to the two becoming a couple and Ospreay becoming a father to Ryan's son. Ospreay said that his family living in England led to him signing with AEW over WWE.

“I really had to do this for my missus, for my son because they need me... There is no disrespect toward them [WWE] at all. I admire anyone who can do it. … After everything, I don’t want to move her anywhere I want her to feel safe and I want her to feel looked after.”

Triple H may have had some choice words about Will Ospreay not being able to handle "the grind" of WWE, but when you learn why he chose AEW, you can tell that he's already able to handle so much more.

This article first appeared on The Sportster and was syndicated with permission.

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