Drafted in the 20th round (620th overall) by the Chicago Cubs in 1999.
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It took Sing three tries to succeed in high Class A, but when he finally did he was the Florida State League's MVP and home run champion in 2004. He earned another homer crown after moving up to the Southern League in 2005, and he set franchise home run records both years. Sing's trademark tool, obviously, is his power. His swing can get long at times, but he has a selective eye and a knack for drawing walks. Where he fits on the diamond and in Chicago's lineup is a question. Sing signed as a third baseman and got a shot at second base in instructional league years ago, but his lack of speed and range limited him to first base or an outfield corner. He does have some arm strength and has committed himself to improving defensively, but he probably won't ever be more than adequate. Blocked at first base by Derrek Lee and in left field by Matt Murton, Sing's best hope of starting for the Cubs is in right field. But they didn't protect him on their 40-man roster, meaning he'll have to continue to prove himself this year in Triple-A.
Sing's third stint in high Class A proved to be the charm. After washing out in a 2003 season marred by mononucleosis and hamstring problems, he destroyed the Florida State League last year. He made a run at the league's home run record, topped the FSL in hits, doubles, extra-base hits and homers, and won the MVP award. Sing worked hard during the offseason to get into the best shape of his career and retooled his swing under the tutelage of Daytona hitting coach Richie Zisk. Sing uses his patience to draw walks and get pitches he can hammer. His swing is a bit long and at 23 he was old for high Class A, so he still has much to prove at higher levels. Sing's position is a problem, and not because he's a below-average runner who's merely adequate at first base. With Derrek Lee ahead of him and top prospect Brian Dopirak behind him, his chances of playing regularly at first base for the Cubs are slim. He broke into pro ball as a third baseman and saw time in instructional league at second base, but his only other option is left field. Sing has a strong arm but not a lot of range. He should open the year as a first baseman in Double-A, moving to left if Dopirak receives a promotion.
More than one Chicago official compares Sing to Richie Sexson because he's tall, rangy and offers plenty of power. He tied for fourth in the Florida State League in homers last year. His .248 average was his career high for a full-season league, though he did offer hope for improvement by showing better plate discipline. Sexson put up roughly similar statistics at the same age, though in Double-A. Sing is agile and has arm strength, but he's still in search of a defensive home. A shortstop in high school, he played third base for his first 21⁄2 years as a pro before the Cubs decided his struggles there were detracting from his bat. He spent the end of 2001 at first base, then played most of 2002 on the outfield corners (more in left field than right) before returning to first in August. At some point he'll have to step up his offensive production regardless of where he settles. Sing will move up to Double-A in 2003.
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Rated Best Power Prospect in the Florida State League in 2004
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