Carlos Zambrano
“Big Z” was an integral part of the rotation in the days of Kerry Wood and Mark Prior. Zambrano made his first impact for the Cubs in 2002 starting 16 games and pitching to a respectable 3.66 ERA. His next four seasons would be solid, winning 15+ games on two separate occasions. Additionally, “El Toro” made three All-Star appearances as a member of the Cubs, in ’04, ’06, and ’08.
On the contrary side, Zambrano did not leave the Cubs on the best of terms after some issues with attitude and fighting in the clubhouse, and the team traded him to the Marlins in 2012. Shortly after that, he announced his retirement.
Zambrano consequently did make a lasting impact for the Chicago Cubs and on a roster of former team prospects belongs.
Rich Hill
Jeff Samardzija was a consideration here, but ultimately Hill is the selection. Hill was a fourth-round pick of the Cubs in the 2002 amateur draft. In 2005 he made his debut for the Cubs.
His rocky career with the Cubs was helped out by an impressive 2007 season. That year Hill went 11-8 with a respectable 3.92 ERA.
Furthermore, Hill has found a way to stick around baseball as his resume includes the Baltimore Orioles, St. Louis Cardinals, Boston Red Sox, Cleveland Indians, New York Yankees, Washington Nationals, and the Los Angeles Dodgers. Hill is quite a story, and it’s quite amazing how he has stuck around for so long and finds himself as the last spot to fill out this rotation.
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In brief, the Cubs have indeed had some excellent prospects over the years. In like manner, to imagine what the current lineup would look like with this level of rotation is a fun thing to ponder. It is also particularly fun of course to believe how the current Cubs lineup would match this fictional roster regarding overall performance. Under these circumstances without some of these guys, the Chicago Cubs will be competitive for a long time.