Cubs: Best and worst free agent signings all-time, by position
Cubs: The shortstop position has overall been a solid position for the Cubs throughout history.
Best: Ricky Gutierrez
He might be known as the guy who had the lone hit against Kerry Wood on May 6, 1998, but he later joined the Cubs and was a very solid player for them. He signed with the Cubs prior to the 2000 season and played two seasons on the North Side. Gutierrez hit .284/.359/.401 with 21 home runs, 98 OPS+, and 122 RBI in 272 games. In 2001 he played in a career-high 147 games and hit a career-high .290. Not much else to say but he quietly played very well for the Cubs. He, like several others on this list, was part of the competitive 2001 team.
Worst: Jeff Blauser
From 1987-1997, Jeff Blauser was a key player in the Atlanta Braves success. Over that time Blauser played in 1,184 games and hit .268/.355/.415 with a 106 OPS+ and 109 home runs. His efforts helped get him make two All Star teams and he won a Silver Slugger award in 1997. On top of all of this, he absolutely mashed Cubs pitching, slashing .351/.413/.611 with a 1.023 OPS in 299 plate appearances.
Prior to the 1998 season the Cubs landed Blauser on a two-year deal. The Chicago Tribune caption literally read, “Cub-Killer Blauser Joins the Team“. Blauser ended up hitting .226/.343/.342 with a .685 OPS in 223 games as a Cub. He would not play with any other team in the Majors after 1999. Naturally, the Cub-killer could not replicate his performance with the Braves.