Three Goals for Ben Cherington at the Winter Meetings

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Win Trades

It is no secret that the Pirates have fared poorly on the trade market in recent years. The trade for Chris Archer easily goes down as the worst trade in the history of the organization and will most likely be one of the worst trades historically in the MLB once the dust fully settles. The Pirates failed to develop a front-end starter in Tyler Glasnow and traded him, traded away another front-end starter in Shane Baz, and traded away a perennial All-Star (most likely) in Austin Meadows. All for Chris Archer – who is a fantastic person – but just has not performed at all with season ERAs of 4.30 and 5.19 in his two years with Pittsburgh.


Tyler Glasnow had a 1.78 ERA as a starter for the Rays this season.

Austin Meadows was an All-Star.

The other trade Neal Huntington will be known for is the Gerrit Cole trade. Huntington traded away Cole for Michael Feliz, Joe Musgrove, Colin Moran, and Jason Martin. Huntington was highly criticized for not landing a top prospect from the Astros. All four of the acquired players would help the Pirates at some point in 2018 and 2019, but none of the four players came anywhere close to the level of production of Cole. Cole had two straight All-Star seasons for the Astros and two straight Cy-Young bids. Once again the Pirates lost big on a trade.

Next. Free Agent Target: OF Kevin Pillar. dark

A small market team like the Pirates can simply just not make mistakes with trades. Failed trades like these can set a small-market organization back for years – and that is not an exaggeration. The margin of error is small and Cherington must be up for the task. He has to win with any larger trades that he makes during these Winter Meetings – and through those trades, earn the trust and excitement that the city of Pittsburgh is so ready to give to a successful and passionate GM.