The Craziest Sports Owners Of All-Time 🧠

The Craziest Sports Owners Of All-Time

David Tepper is officially the Worst Owner in sports.

Throwing a drink at a fan was wild enough to land him on the All-Time Crazy Owner List.

Some of these guys had ZERO business owning a team:

Ted Stepien (Cavs 1980-1983)

  • You know you suck when they name a rule after you

  • He went into the ultimate WIN NOW MODE by trading every 1st rounder possible and got meaningless players in return…

  • Today teams can’t trade 1sts in consecutive seasons, “The Stepien Rule”

John Spano (Islanders 1996-1997)

  • Spano was a master con-man

  • He built such a big reputation that he talked his way into buying the Islanders

  • But there was one problem…he had no money

George Steinbrenner (Yankees 1973-2010)

There’s so many, but here’s two of my favorites:

  1. He fired and re-hired manager Billy Martin 5 different times

  2. After multiple failed attempts to trade Dave Winfield, Steinbrenner paid $40k to a Bronx gambler to obtain damaging information about Winfield

He was permanently banned from overseeing day-to-day operations

Dan Gilbert (Cavs 2005-Present)

  • After Lebron left, Gilbert wrote a public letter stating…

  • "I PERSONALLY GUARANTEE THAT THE CLEVELAND CAVALIERS WILL WIN AN NBA CHAMPIONSHIP BEFORE THE SELF-TITLED FORMER 'KING' WINS ONE"

  • LeBron won with Miami…and Gilbert re-signed him

Frank McCourt (Dodgers 2004-2012)

  • Our first look into an owner who used the “supernatural” to aid his team

  • Mccourt hired an old Russian healer, named Vladimir Sphunt to send good energy to his team

  • McCourt paid him a  yearly salary for 5 years…The Dodgers did not win the World Series in that time

Harry Frazee (Red Sox 1916-1923)

  • Frazee authored the worst trade in sports history

  • He sent Babe Ruth to the Yankees for cash considerations

  • Not to finance his team…but his upcoming broadway musical “No Nanette”

Charlie Finley (A’s 1960-1980)

  • The most petty owner on the list

  • When the A’s won the World Series, he was angry that not enough players sent him “Thank You” notes

  • So instead of diamonds in their World Series rings…he chose glass

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