Pirates History: Pittsburgh slugger's prudent contract extension somehow turned bad

Over the years, the Pirates have utilized their money through contract extensions. In fact, the Pirates are on a three-year streak of extending a player, including Ke'Bryan Hayes, Bryan Reynolds, and Mitch Keller.

It's tough to have a whole lot of complaints so far about those extensions, but looking back over the last decade, one slugger's early extension certainly stands out as a cautionary tale.

The Gregory Polanco contract extension hurt the Pirates more than it helped them.

The hype around Gregory Polanco coming through the farm system was so high. The international signing out of the Dominican Republic began his career in 2009 and quickly rose through the Pirates' minor-league system. By 2013, the year before making his debut, Polanco had put together a 123 wRC+ with an OPS of .791 across three levels.

He was looking like the next big thing during the Pirates' playoff window in the mid 2010s. After coming up 2014 and putting together a slightly below average season, he still entered 2015 with the starting job. He put up a 92 wRC+ with a .701 OPS, 27 stolen bases, and an fWAR of 2.2.

In April the very next year, the Pirates decided to extend Polanco to a five-year deal worth $35 million, which came as a surprise, skipping arbitration completely. Pittsburgh does not often do such things to erase the cheapest moments of a player's career, but the hype around Polanco changed everything for them.

He followed that extension with a solid 2016 season, belting 22 home runs and posting a wRC+ of 106. Then came a career-worst season that fueled his career-best campaign in 201,8 where he slugged 23 homers and produced a wRC+ of 123. Unfortunately, that was his clear peak; he ended that season with a shoulder injury that put him into a steady decline, leading him to put up a negative fWAR in each season thereafter.

When Polanco was able to post 20+ homer seasons, it seemed he'd be worth the extension, but after 2018, the Pirates were stuck with an expensive, lousy right fielder who lost all his arm strength and struck out at career-high rates. That made this one an extremely poor extension choice, given that he followed the contract with a trip overseas to continue his career in Japan.