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43. Ed Reulbach

A Pitcher for the back-to-back World Series Championship teams in 1907 and 1908, Ed Reulbach was the beneficiary of playing for some potent Cubs teams.  It certainly didn't hurt his winning percentage as he would lead the National League three years in a row in that category (1906-08), and he had at least 17 Wins in his first five years.  The success of his team didn't mean that he didn't help his cause as he had an ERA under 2.00 in four of those years, all of which were good enough for a top six finish.  Reulbach would also lead the NL in H/9 in 1905 and 1906.

47. Derrek Lee

A World Series Champion with the Florida Marlins in 2003, Derrek Lee was one of the many players who was jettisoned off in their fire sale.  Lee would play for the Cubs for six and a half seasons, where he had 1,046 for the team with a beautiful Slash Line of .298/.378/.524 and was a two-time All-Star.  He will always be remembered for his spectacular 2005 season, where he won the Batting Title (.335), Slugging Title (.662), and OPS Title (1.080), and he would have career highs in Home Runs (46).  He would finish third in MVP voting that year, and he would also have a ninth place finish in 2009.

50. Jake Arrieta

It is safe to say that midway through the 2013 season that when the Baltimore Orioles traded Jake Arrieta (with Pedro Strop) for Steve Clevenger and Scott Feldman that the Cubs got the better end of the deal.

40. Kiki Cuyler

While Kiki Cuyler’s best years in baseball were as a Pittsburgh Pirate, he actually spent more time with the Chicago Cubs.  Playing 949 Games for Cubs, Cuyler would have five seasons where he batted over .300, two of which would see him exceed .350.  Cuyler's first three years in Chicago (1928-30) would see him lead the National League in Stolen Bases, and he would also finish first in Doubles in 1934.  Overall, he batted .325 with 1,199 Hits for the Cubs, and he would be chosen for the Baseball Hall of Fame in 1968 when he was voted in by the Veteran's Committee.  The Cubs would also place Cuyler into their Hall of Fame in 2021, the first year of their exstence.