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As George is suggesting changes in the team's uniforms, at a Yankee game with Elaine, Jerry meets Karen Hanson, the Miss America contestant from Rhode Island. Because pageant rules forbid her from going out alone, when Jerry learns Karen's regular chaperone is unavailable he asks Kramer to fill in. Meanwhile, Elaine interviews for Jacqueline Onassis old job at a big publishing house. And, though turned down for the editor's spot, a chance encounter with the former First Lady's companion leads to her working as his assistant.
Claiming extensive knowledge of the pageant and its history, Kramer readily accepts the offer to chaperone. But, after he steadfastly refuses Jerry's suggestion that he keep a low profile, the date is ruined when Kramer is hired as Karen's pageant consultant. As Kramer sets out to make Karen the next Miss America, Jerry invites George to Atlantic City for the pageant weekend, though Elaine is unable to join them because new boss Justin Pitt desperately needs new socks. Meanwhile, after giving Yankee player Danny Tartabull some tips on his swing, George convinces manager Buck Showalter to switch from polyester to cotton uniforms.
As Kramer prepares Karen for the pageant and Elaine struggles to find just the right socks for her demanding boss, Jerry and George are disturbed by some noisy birds outside their hotel room window. However, after Jerry uses a bucket of water to quiet them, Karen wakes to find the trained doves for her magic act have been mysteriously drowned. Suspecting they were murdered, Kramer then spots the telltale ice bucket and accuses Jerry of sabotaging Karen's chances at becoming Miss America. Forced to sing in the talent competition instead, Karen is roundly booed by a hostile pageant crowd as Jerry, George, Elaine and Justin all watch on TV. Finally, George's idea becomes a nightmare for the Yankees when the new uniforms shrink after their first washing.
"The Chaperone" featured appearances by Danny Tartabull and Buck Showalter, both at the time part of the Yankees as player and manager, respectively. The scenes in the Yankees' locker room were actually shot at the Anaheim Angels' locker room when the Yankees were playing the Angels – weeks and in advance of the show's other scenes.
Ian Abercrombie auditioned for the part of Mr. Pitt on August 9, 1994 at 3:00 in the afternoon.
The name "Mr. Pitt" was a late substitution for the name "Maurice Templesman." Templesman, a mysterious millionaire diamond merchant, was the last love of Jackie Onassis. Templesman declined to permit Seinfeld the right to use his name, so the character was changed to Justin Pitt. Despite the change, Elaine still won the character's attention because she happened to be dressed like Jackie Onassis.
Though he didn't receive on-screen credit, Regis Philbin performed the voice over for the Miss America emcee.
MISS RHODE ISLAND:
"No, thanks. I'm watching my weight."
"Ah. I'm watching my height. My doctor doesn't want me to get any taller."