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Some of the most momentous deals in MLB history have gone down right as the deadline was about to hit.

Gleyber Torres looks to become one of the all-time great Yankees, despite a tough start to 2020, and the Chicago Cubs won the 2016 World Series. It's very likely that neither one of these statements would be true had the Cubs and Yankees not negotiated a trade involving these two players. It's one that could truthfully be labeled as a win-win trade.


But that's not the case too often throughout the thousands of deals that have gone down over time. One-sided deals are great representations of the risk that comes with swapping unknown prospects, aging veterans and other commodities. Just ask Nolan Ryan, Jim Fregosi and the New York Mets -- though this deal did not occur at the deadline, but in the offseason. So too did the deal that sent Frank Robinson to the Baltimore Orioles, and so on.

With the 2020 MLB Trade Deadline set for Monday, August 31 at 4:00 pm -- one that may not be the most exciting we've ever seen because of the strange circumstances surrounding the season -- we take a look back at some midseason deals that left one team as a clear winner, and one as a big, big loser.

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