The Worst Trade Deals That Ever Happened in MLB

A trade deal can make or break a season, and it's something that every team needs to balance to perfection every year. As the deadline looms, the pressure grows, and if the team hasn't already bagged the required players, managers can come under extreme stress to make a switch. 

Unfortunately, not all MLB trades go as planned - as fans of MLB betting will be able to testify to. Here’s a look at some of the deadline deals done that would have been better left unsigned.

This 2018 was one to remember with Glasnow, Meadows and Baz all going from the Pirates, with the Rays sending Chris Archer in the opposite direction. For a long time, it didn't look as if the deal would be done, as the Rays could have held onto Archer for one more year. 

The lure of getting two of the best young talents from Pittsburgh, plus their first pick from 2017, was too much for the Rays to ignore. 

The move turned out to be phenomenal for the Rays, with Meadows becoming an All-Star in 2019, plus Glasnow performing exceptionally well. On the flip side, Archer hasn't found his feet in Pittsburgh and missed the whole of the 2020 season due to injury.

The Cubs were so keen to land Rich Harden before the 2008 deadline that they were willing to offer a package of four players to Oakland in return. The deal was done with Harden heading to Chicago and Josh Donaldson and three prospects heading in the opposite direction. 

Although the Cubs were sure they'd done a great trade, it didn't really work out so well. Harden was outstanding at the tail end of 2008, with a 1.77 ERA from 12 starts. Unfortunately, he never recaptured that sizzling form and disappointed on the mound. 

At Oakland, the three prospects never really delivered on their early promise, but Oakland were still left smiling due to the form of Josh Donaldson. He performed so well in 2013 that he finished in the top eight players in the MVP voting and again the following year. In 2015 he was traded to Toronto, where he eventually won the award.

This was the tale of two pitchers, with the Cubs trading Ryan Dempster in return for Kyle Hendricks from Texas Rangers. The switch occurred in 2012, and the Cubs got the best out of the deal. 

Before moving, Ryan Dempster had 16 starts and an ERA of 2.25 but didn't manage to capture the same form in Texas. In 12 starts, he posted a shocking 5.09 ERA, way below the expected performance. In contrast, it may have taken Hendricks a further two years to make the majors after the switch, but he proved to be a solid pitcher notching up 162 starts in six seasons with an ERA of 3.14.