Chicago Cubs: Revisiting the Kyle Hendricks and Ryan Dempster deal

In the Theo Epstein era, the Chicago Cubs have won a number of trades. But has one been more lopsided than the deal that brought Kyle Hendricks to Wrigley?

I’ll admit, sometimes I feel like Kyle Hendricks is a home-grown product of the Chicago Cubs. He’s spent all five of his big league seasons on the North Side, won a World Series and came close to winning the National League Cy Young award in 2016.

However, Hendricks’ career with the Cubs very nearly didn’t happen and it wouldn’t have if not for former Cub Ryan Dempster. I say that because Dempster really played a role in getting Hendricks to Chicago.

At the 2012 trade deadline, Dempster was one of the hottest pitching targets on the market. He was in the midst of one of his best seasons with the Cubs, carrying a 2.25 ERA, which was the second lowest in the National League. He had 83 strikeouts and had walked just 27 batters while surrendering nine home runs in his 16 starts.

As for the Cubs, they were going nowhere. They had a record of 43-59 and were the fourth-worst team in the National League. They were looking to move assets which could help bring back prospects for the future. Dempster was a 35-year-old who was set to be a free agent at season’s end. He was the perfect candidate to move at the deadline.

This is where Dempster really helped out the Cubs, he held a trump card. Since Dempster had been in the big leagues for 10 years and was with the same team for five years he held 10-and-5 rights and could reject a trade. At one point, Dempster did, in fact, veto a trade the Cubs had lined up with the Atlanta Braves. He was later rumored to be dealt to the Los Angeles Dodgers but they apparently refused to part ways with Allen Webster so the deal fell apart.

This led to Theo Epstein and the Cubs making a deal that sent Dempster to the Texas Rangers for prospects Hendricks and Christian Villanueva. At the time, it was a trade that made sense for both teams.