By Bruce Levine–

(CBS) — The return to the field for Cubs right-hander Edwin Jackson has some irony and large challenges to overcome at the same time. Jackson has been sidelined since Aug. 21 with a lat problem in his right shoulder. His two seasons with the Cubs have been an abject failure and frustration for the people who signed him and Jackson himself.

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Jackson is a high-quality person and teammate, but the record couldn’t be worse. A composite 14-32 with a 5.50 ERA during his time in Chicago has been a hard pill to swallow for pitcher and organization as well.

Jackson will pitch Friday against Los Angeles, the team that originally drafted him in 2001. The Dodgers also send the best starting pitcher in baseball to the mound to face Jackson and the Cubs. Clayton Kershaw, with a gaudy 19-3 record and 1.70 ERA, will be the latest obstacle.

“The rehab has been mostly rest and recovery,” Jackson said Wednesday. “It was not an injury where I needed super vigorous rehab. It is always fun when you are going against guys like Kershaw. It makes the game interesting, but you don’t really think about pitching against Kershaw, I mean, you are still pitching against the (team) — you have eight other guys swinging the bat.”

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Jackson will be held to a strict pitch count, probably 60 to 70 pitches, after missing almost a month.

“I will go as hard as I can for as long as I can,” he said. “I hope to finish the year on a good note.”

The Cubs still must pay $11 million in both 2015 and 2016 to Jackson, who signed a four-year, $52-million deal before the 2013 season. The contract included an $8 million signing bonus and four years at $11 million-per.

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Bruce Levine covers the Cubs and White Sox for 670 The Score and CBSChicago.com. Follow him on Twitter @MLBBruceLevine.