Some of the Chicago Cubs best and worst moves at the trade deadline

CHICAGO, IL - OCTOBER 18: Jake Arrieta #49 of the Chicago Cubs receives a standing ovation after being relieved in the seventh inning against the Los Angeles Dodgers during game four of the National League Championship Series at Wrigley Field on October 18, 2017 in Chicago, Illinois. (Photo by Jamie Squire/Getty Images)
CHICAGO, IL - OCTOBER 18: Jake Arrieta #49 of the Chicago Cubs receives a standing ovation after being relieved in the seventh inning against the Los Angeles Dodgers during game four of the National League Championship Series at Wrigley Field on October 18, 2017 in Chicago, Illinois. (Photo by Jamie Squire/Getty Images) /
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(Photo by Norm Hall/Getty Images) /

Chicago Cubs get their big game pitcher in Hendricks

At the 2012 deadline the Cubs held the top rental arm on the market in Ryan Dempster. The Cubs had a record of 43-59 and were going nowhere and had every intention of flipping Dempster for prospects.

While Dempster was set to be a free agent, he also held a trump card, as he had full veto power due to his 10-and-5 rights. He did in fact use that power that blocked a trade to the Atlanta Braves. That resulted in him being dealt to the Texas Rangers for Kyle Hendricks.

During the Cubs stretch of success, Hendricks has become an integral part of the starting rotation. In his six years he’s posted a record of 59-41 while pitching to the tune of a 3.26 ERA. He posted a career-low 2.13 ERA in 2016, where he finished third in the National League Cy Young voting.

Hendricks has gone on to pitch in some of the biggest games in Cubs history. He won Game 6 of the NLCS against the Los Angeles Dodgers that sent the Cubs to the World Series. He also started Game 7 of the World Series against the Cleveland Indians, a game he pitched exceptionally well in.

As for Dempster, he didn’t have the greatest second half with the Rangers. He made 12 starts where he posted a 5.09 ERA. The Rangers made it to the wild card game but ended up losing to the Baltimore Orioles.

Dempster walked away at the end of the season and signed with the Boston Red Sox. The right-hander would pitch just one season for the Red Sox, before deciding to hang up the cleats and retiring from baseball.

As sellers at the deadline the Cubs came out incredibly well in this deal. Flipping Dempster, an aging pitcher in the final year of his contract for Hendricks, a young, up-and-coming pitcher was truly a steal.