Chicago Cubs: 5 reasonable free agents to target this offseason

LOS ANGELES, CA - OCTOBER 09: Howie Kendrick #47 of the Washington Nationals hits a grand slam in the top of the tenth inning to take a 7-3 lead during Game 5 of the NLDS between the Washington Nationals and the Los Angeles Dodgers at Dodger Stadium on Wednesday, October 9, 2019 in Los Angeles, California. (Photo by Rob Leiter/MLB Photos via Getty Images)
LOS ANGELES, CA - OCTOBER 09: Howie Kendrick #47 of the Washington Nationals hits a grand slam in the top of the tenth inning to take a 7-3 lead during Game 5 of the NLDS between the Washington Nationals and the Los Angeles Dodgers at Dodger Stadium on Wednesday, October 9, 2019 in Los Angeles, California. (Photo by Rob Leiter/MLB Photos via Getty Images) /
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WASHINGTON, DC – OCTOBER 07: Rich Hill #44 of the Los Angeles Dodgers delivers in the first inning against the Washington Nationals in game four of the National League Division Series at Nationals Park on October 07, 2019 in Washington, DC. (Photo by Will Newton/Getty Images)
WASHINGTON, DC – OCTOBER 07: Rich Hill #44 of the Los Angeles Dodgers delivers in the first inning against the Washington Nationals in game four of the National League Division Series at Nationals Park on October 07, 2019 in Washington, DC. (Photo by Will Newton/Getty Images) /

2. Rich Hill

Entering his age-40 season, left-hander Rich Hill has expressed a desire to continue pitching. His first choice is to remain in Los Angeles with the Dodgers, but it is unclear if the Dodgers are interested in meeting his asking price or guaranteeing him a contract. Whether or not he would consider pitching for a different team remains to be seen. Hill has waffled on retirement, but keeps finding the motivation to take the mound.

Hill’s second act since returning to the big leagues at the end of the 2015 season with the Boston Red Sox has been one of the most stunning resurgences in the league. He is 41-20 with a 2.91 ERA over the last five seasons and has struck out 10.7 per nine while allowing only 6.7 hits per nine. Hill hasn’t been able to manage more than 25 starts in a season, but he has been ready in the playoffs every year.

The Chicago Cubs need to fill out the back of their rotation and can offer Hill a place to finish up his career if he cannot work something out with the Dodgers. Since returning to the big leagues, Hill has made 12 playoff appearances and has a 2.70 ERA while holding opponents to a .196/.319/.274 line. The Cubs can bring him along slowly in the first few months of the regular season and ramp him up for the stretch run.

The big wild card here is Hill’s desire to move his family from Los Angeles. Returning to Chicago would make for an interesting conclusion to a long, winding career. Hill spent the first four years of his career with the Cubs and was 18-17 with a 4.37 ERA in 64 games.