Kaitlin Olson Outbid Rob McElhenney For Princess Diana Eagles Jacket, And She Absolutely Roasted Him For It In Front Of Jason And Travis Kelce

Kaitlin Olson and Rob McElhenney on It's Always Sunny in Philadelphia.
(Image credit: FXX)

Rob McElhenney has been married to his It’s Always Sunny in Philadelphia co-star Kaitlin Olson for 15 years, so the amount of comedic talent in their household is just unfair. But Olson really pulled one over on her husband when it came to their shared love for the Philadelphia Eagles, as she not only secretly outbid him in an auction for an autographed Eagles jacket, she absolutely roasted him over it in front of Jason and Travis Kelce.

The jacket in question was a Philadelphia Eagles letterman jacket autographed by Jason Kelce’s wife Kylie, and was the same style as the one Princess Diana famously wore back in the ‘90s. Proceeds from the auction were to benefit the Philadelphia Eagles Autism Foundation, and Rob McElhenney was all too happy to offer $10,000 for such a good cause. But then someone bid $20,000, so he raised his price, and a bidding war ensued. He explained the situation to the Kelce brothers in a clip from the New Heights podcast, saying: 

I couldn't believe that somebody was immediately jumping on every time I bid, and so my final bid was going to be representing my favorite player on the Eagles, 62. I thought that [$62,000] was a good number. I thought that was a number that would resonate in the hearts and minds of Birds fans all over the world, and again, was for a foundation that we feel really strongly about, that we really love and believe in.

Rob McElhenney recalled being confused about being outbid, so he set his final bid at $62,000 in honor of Jason Kelce’s jersey number. That’s when he apparently got a text from his wife, who had seen his generous offer going viral on social media. The Welcome to Wrexham star continued: 

And then I got a text from somebody that I know who said, ‘I've been the one bidding against you, bozo.’ And it did not even cross my mind that this was a possibility, and it turned out I live with this person.

Travis and Jason Kelce were thoroughly shocked and excited when Kaitlin Olson entered the chat, shouting their praise for how she pulled off the “inside job.” The actress, aka Sweet Dee from one of the funniest shows on Hulu right now, then proceeded to jokingly roast Rob McElhenney for having no idea it was her the whole time. Olson said: 

This moron, OK, we live in the same house. This is a foundation that’s important to both of us. The jacket looks great on [Jason’s] wife. It’s clearly for women. I want it. He mentions nothing about it. I’m like, ‘What are you doing?’

Rob McElhenney admitted it really didn’t make any sense for the jacket to go from Princess Di to Kylie Kelce to “a dude,” and he and Kaitlin Olson decided to make it a nice round $100,000 to secure the jacket for the Hacks actress. Olson concluded: 

I win, basically. I win. I win. I won the jacket for sure. He will not be wearing the jacket ever.

Might we possibly see the famed jacket on a future episode of It’s Always Sunny in Philadelphia? We’ll have to wait to find out, but in the meantime you can rewatch any of the first 16 seasons with a Hulu subscription while we wait for Kaitlin Olson’s upcoming show High Potential. Hulu is also where you can see Rob McElhenney and Ryan Reynolds run their football club on Welcome to Wrexham

Heidi Venable
Content Producer

Heidi Venable is a Content Producer for CinemaBlend, a mom of two and a hard-core '90s kid. She started freelancing for CinemaBlend in 2020 and officially came on board in 2021. Her job entails writing news stories and TV reactions from some of her favorite prime-time shows like Grey's Anatomy and The Bachelor. She graduated from Louisiana Tech University with a degree in Journalism and worked in the newspaper industry for almost two decades in multiple roles including Sports Editor, Page Designer and Online Editor. Unprovoked, will quote Friends in any situation. Thrives on New Orleans Saints football, The West Wing and taco trucks.