10 Most Infamous Wrestling Losing Streaks

1. Shelton Benjamin

Curt Hawkins
WWE.com

Usually, the end of a losing streak is a moment of catharsis to the wrestler subjected to it. Their heat with the office has either dissipated, or the initial source of friction has been forgotten about entirely.

Not so much for Shelton Benjamin. His 2005 losing streak wasn't a punishment for a backstage transgression - it was a way of introducing to him a new manager, one who took it upon themselves to galvanise the gifted technician and navigate his route to the main event. Wrestling has a glorious history of managers compensating for the charismatic deficiencies of those in their charge - a trope which has been left to gather dust for much too long.

That tradition wasn't exhumed; instead, Benjamin was accompanied to the ring by his mother - or, more accurately, what WWE's gigantically racist creative team assumed what the mothers of African American athletes looked like.

Momma Benjamin was an obese, loud, ultra-annoying woman - one who slapped and berated her son in the aftermath of his losses, before ensuring victories by interfering on his behalf. The character was such a lead balloon that you suspect Benjamin was happier losing on his own accord.

Contributor
Contributor

Michael Sidgwick is an editor, writer and podcaster for WhatCulture Wrestling. With over seven years of experience in wrestling analysis, Michael was published in the influential institution that was Power Slam magazine, and specialises in providing insights into All Elite Wrestling - so much so that he wrote a book about the subject. You can order Becoming All Elite: The Rise Of AEW on Amazon. Possessing a deep knowledge also of WWE, WCW, ECW and New Japan Pro Wrestling, Michael’s work has been publicly praised by former AEW World Champions Kenny Omega and MJF, and current Undisputed WWE Champion Cody Rhodes. When he isn’t putting your finger on why things are the way they are in the endlessly fascinating world of professional wrestling, Michael wraps his own around a hand grinder to explore the world of specialty coffee. Follow Michael on X (formerly known as Twitter) @MSidgwick for more!