As long as sports have been played in organized leagues, there have been team owners who have disgraced their respective games. Scoundrels, cheapskates and spoiled brats have always found a way to rip defeat from the jaws of victory — none worse than these 10 worst owners in sports history.

1. Harry Frazee, Boston Red Sox (1916-1923)

Fans love it when their team signs a big-name free agent or locks up a current star, but too many times organizations pay for past accomplishment instead of future production. There are obviously some baseball superstars on this list, but unfortunately much is expected from those who have been compensated at the highest level. Here’s our look at the 10 worst contracts in major league baseball.

The tumultuous one-year tenure of Bobby Valentine in Boston is over. The Red Sox were awful under the polarizing manager, and the 2012 season was the first time the franchise had lost 90 or more games since 1966. There was constant turmoil between players and Valentine in the Boston clubhouse, as well as bickering between both parties in the media. The 69-93 campaign saw general manager Ben Cherington change the club’s philosophical direction by trading away veterans Kevin Youkilis, Adrian Gonzalez, Josh Beckett and Carl Crawford.

Trading baseball players between teams has been part of the charm of the game since the 1800s. Ornery players traded after disputes with managers, struggling players traded for one another in hopes that a change of scenery will bring life back to their game, aging stars traded for young prospects, pitching traded for hitting, difficult contract negotiations avoided by trades, financially embarrassed teams trading players for cash — the game has seen all kinds of reasons for swapping players.

This is your daily link roundup of our favorite sports posts on the web for April 20.

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Regardless what the standings look like now, with the New York Yankees and the Boston Red Sox teetering near the bottom of the AL East, they are not likely to end the season there. The Baltimore Orioles are bad enough that they won’t let it happen this season, but just in case you’re wondering, the last time the Yankees and Red Sox finished last and next-to-last in their division/league was in 1966. The only other time was way back in 1925.

AL East
1. New York
2. Tampa Bay (wild card)
3. Boston
4. Toronto
5. Baltimore