Cubs: Best and worst free agent signings all-time, by position

Cubs: Hitting on free agents is not always easy, the history of the Cubs proves that signings are always a gamble regardless of the resume.

The long history of the Chicago Cubs franchise has seen star players come in by all possible means, trades, drafting, free agency, amateur free agency, etc. Free agency itself has been such a mixed bag for the Cubs over the years, but that is pretty much the case with every team. Not every signing is going to go as expected, for better or for worse.

That is what the main focus of this article is going to be. We will look at free agent signings the Cubs have made in their history for each position and determine which ones were the best, and which ones were the worst. Of course, much of this is arbitrary among fans, but some are more obvious than others. We know who many of the absolute best and worst free agent signings of all time are, but it is much more interesting when you look at it by every position.

It is worth noting before proceeding into the slideshow that there are certain criteria for the upcoming list. First, this is free agent signings only, and amateur free agents do not count. Draft and trades obviously do not count, but more specifically trades then signing extensions also do not count. So for example, anyone who was traded here but got an extension or re-signed right away after the deal was done (i.e. Dexter Fowler) will not count. However, guys who left and then came back will count.

Without further ado, here are the best and worst free agent signings in Cubs history by position.

Cubs: Free agent starting pitching can be one of the biggest gambles in baseball considering the pressure that is one them.

Best: Jon Lester

I doubt people expected different. Jon Lester signed the six-year deal with the Chicago Cubs in December, 2014 as the team was coming out of the rebuild and into contention. Theo Epstein reunited with his former Boston colleague in one of the biggest signings of the offseason. The goal was to bring in the multi-time All Star and postseason master to replicate the success he had in Boston and help bring the Cubs that elusive World Series title.

He did just that. Lester pitched to a 3.64 ERA, 3.86 FIP, 1.25 WHIP and 940 strikeouts in 171 starts as a Cub. In the postseason he was co-NLCS MVP in 2016 and won Game 5 of the World Series, beginning their historic comeback to claim the title. He was also a two-time All Star and Cy Young finalist in 2016 during his time in Chicago. The fans loved him, he loved the fans, he was worth every penny.

Worst: Danny Jackson

Jackson had a pretty decent career as an MLB pitcher. He pitched 15 years in the Majors and posted a 4.01 ERA and 3.77 FIP in 353 appearances. He also won two World Series titles Royals and Reds, and was a two-time All-Star.

However, his time with the Cubs was brutal. In 1991 he signed a four-year, $10.5 million deal to be the next ace; at the time this was a lot of money. Jackson ended up pitching in only 183 2/3 innings on the North Side and posted a dismal 5.19 ERA, 4.47 FIP, 1.6 WHIP and a 5-14 record (win-loss record actually mattered to people back then).

In July, 1992 he was traded to the Pirates for infielder Steve Buechele (who was actually halfway decent for the Cubs). Naturally after he left Chicago he followed up with some very solid seasons with Pittsburgh and Philly.

Cubs: Most of the great Cubs catchers came to the franchise by other means, but there were some notable free agent ones.

Best: Joe Girardi

Girardi might have been drafted and brought to the Majors by the Cubs, but after lengthy stints in Colorado and New York the Cubs brought him back via free agency in 2000. It was his second stint with the Cubs he played at his best.

In 2000 he made his one and only All-Star appearance, hitting .278/.339/.375 in 106 games. He was then part of the 2001 Cubs team that posted a winning record and spent time in the playoff hunt. Girardi was a respected teammate and well liked by the fans, and he felt right at home again considering he also was from Evanston, Illinois.

Worst: Todd Hundley

Decades ago, Randy Hundley was a very popular player for the Cubs. He was part of the 1969 team that was on the verge of making the playoffs until the “Miracle Mets” dashed their hopes. As for his son Todd, he was not so popular. Todd Hundley was a longtime New York Met, and was very successful there. He was a two-time All Star and slugged 124 home runs, including a 41-home run season in 1996, in 829 games with the Mets.

Hundley signed a four-year, $24 million deal in 2001. His tenure as a Cub saw him hit just .199/.285/.398 in 171 games before being dealt to the Dodgers after the 2002 season. What made things worse is that he had some personal beef with the team and fans, which did not do him any favors. Flipping obscene gestures to heckling fans do not get forgotten easily.

Cubs: One of the biggest signings in franchise history included a guy who primarily played second base.

Best: Ben Zobrist

He might have been a utility guy, but we will count him in this. Zobrist was one of the final pieces needed to win a World Series championship in 2016. After winning a World Series with the Kansas City Royals in 2015, the veteran utility man signed a four-year, $56 million deal prior to the 2016 season. His ability to switch hit, put the bat on the ball and get on base was an ideal fit for a young lineup.

Zobrist had established himself in Tampa Bay and had played with then-Cubs manager Joe Maddon there. In his first season as a Cub he made the All-Star team, and went on to win the World Series MVP award after driving in the go-ahead run in Game 7 and hitting .357/.419/.500 in the Fall Classic. Overall he hit .269/.362/.411 with a 104 OPS+ in 461 games as a Cub. Worth every penny.

Worst: Neifi Perez

This is a name that fans love bringing up in, “Hey! Remember that guy?” conversations. Perez came to the Cubs organization as a free agent in August 2004 after a rough year in San Francisco. The veteran infielder had a nice run with Colorado, hitting .282/.313/.411 from 1996-2001. He also won a Gold Glove in 2000. His tenure with the Cubs was very blah. While a .276 average is certainly not terrible, he put up a .297 OBP, .681 OPS and 74 OPS+. That is…not good.

Perez was a regular on the field and ended up playing in 154 games in 2005. They did not break the bank on him, and he was certainly not the worst free agent signing ever, but many would agree he got way too much playing time for the production he was putting up. At least he is a fun footnote in Cubs trivia.

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.

Cubs: The team has had so many great players at the hot corner, but not many have come in via free agency.

Best: Vance Law

The former White Sox and Expos infielder came to the Cubs in 1988, and he put together a nice tenure on the North Side. Law would play two seasons with the Cubs and he hit .269/.332/.388  with a 101 OPS+ in 281 games. In 1988 he made his one and only appearance in an All-Star game as he hit a career-high .293 and 78 RBI. The following year he was part of the “Boys of Zimmer” Cubs team which won the NL East. Not a bad find for the Cubs.

Worst: Brent Lillibridge

Remember Brent Lillibridge? If you do, good for you. After spending most of his MLB career with the White Sox, the Cubs brought him in for the 2013 season to play at third. It was not a big signing by any means and he did not last very long with the Cubs. He played in only nine games and recorded one hit in 24 at bats with zero walks and two RBI. He was DFA’d and purchased by the Yankees in June. If you really want to play a fun game of “Obscure Cubs”, this is one to add to the list.

Cubs have had some solid luck finding left fielders in the free agent market.

Best: Moises Alou

It was back and forth between Alou and Dave Kingman, but we will go with Alou here. Alou has a spot in the mythical, “Hall of Very Good” as he had an impressive and long MLB career. He is one of 11 players in MLB history to retire as part of the 300-300 club (between 300-399 home runs and a .300+ average).

From 2002-2004 the slugging left fielder called Wrigley Field home after the Cubs signed him to a three-year, $27 million deal. In those three seasons he hit .283/.353/.484 with an .837 OPS, 116 OPS+, 258 RBI and 76 home runs. He made one of his six career MLB All-Star Games in 2004 when he hit a career-high 39 home runs.

While he is most remembered for the infamous “Bartman play” in Game 6 of the 2003 NLCS, the guy was an incredibly good ballplayer and delivered consistently as a Cub. In terms of ranking all-time signings regardless of positions, he is arguably top-five.

Worst: Candy Maldanado

He played all over the outfield, but we will count him as a left fielder for this list. Maldonado was a solid ballplayer from 1981-1992, hitting .258/.321/.425 with 124 home runs and a 109 OPS+. He was part of the 1992 World Series champion Toronto Blue Jays team as well.

Prior to the 1993 season he signed with the Cubs. He only played in 70 games as a Chicago in 1993 before being traded to Cleveland, and in those games as a Cub he hit a dismal .186/.260/.286 with three home runs and an OPS+ of 48. Yikes. The North Side was not sweet for the Candyman.

Cubs: Right field free agents have seen some big hits and big misses.

Best: Andre Dawson

Hall of Fame right fielder Andre Dawson spent six years as a member of the Cubs and is considered one of the best players in franchise history. “The Hawk” had tremendous power at the plate and a rocket for an arm. Five of his six years in Chicago he made the NL All-Star team, which was especially great in 1990 when the mid-summer classic was played at Wrigley Field. Dawson as a Cub slugged 174 home runs, slashed .285/.327/.507 with a 125 OPS+, .843 OPS and 587 RBI.

Despite being on a losing team he won the 1987 NL MVP award, leading baseball in home runs (49), RBI (137) and the NL in total bases (353). The best part of him signing as a free agent? The Cubs literally handed him a blank contract for him to fill out. Not only the most unique free agent signings in team history but ended up being one of the best. Dawson was elected to Cooperstown in 2010 and despite his plaque showing him wearing an Expos hat, his time with the Cubs is well remembered by baseball fans.

Worst: Milton Bradley

Whether it was his underachieving play or his disgusting attitude, Milton Bradley will be seen by many as one of the worst signings in franchise history, period. Bradley was signed by Jim Hendry prior to the 2009 season on a three-year, $30 million contract. The veteran outfielder was an All Star with the Texas Rangers the year prior, hitting a career-high 22 home runs and leading the AL in OBP (.436), OPS (.999) and OPS+ (162).

From a production standpoint, it made sense, but many were wary about his past attitude problems. Sadly he neither improved his attitude nor played up to expectations. Bradley got into it with his manager, his teammates did not like him and he chased himself out of Chicago after hitting only 12 home runs with an OPS of .775 and 100 OPS+. The numbers are pretty average, not horrible, but he was expected to do a lot more. He was eventually traded to Seattle after the 2009 season for Carlos Silva. Shame he was his own worst enemy because in his prime he was a very good hitter.

Remember when Bradley threw the ball into the stands with two outs? That summed up his Cubs tenure right there.

Cubs: Finding the number of starting center fielders that came to the Cubs via free agency was not easy.

Best: Jim Edmonds

Cubs fans might not like this, but longtime nemesis Jim Edmonds fit incredibly well on the 2008 division champion team. The longtime Angel and Cardinal obliterated Cubs pitching in his career and was seen as one of the team’s biggest villains. When he signed with the Cubs in 2008, after a brief failed stint in San Diego at the ripe age of 38, North Side fans wanted to puke.

However, the veteran slugger and eight-time Gold Glove winner came up so big in his 85 games as a Cub. He slashed .256/.369/.568 with 19 home runs, a .937 OPS, 135 OPS+ and 17 doubles. On June 21, he homered twice in the fourth inning against the White Sox. While his time in Chicago was brief and he is still probably seen as a Cubs villain, cannot discredit him for his contributions in a Cubs uniform.

Worst: Willie Wilson

We had to give it to someone, so Willie Wilson is the somewhat unfortunate receiver of this dishonor. Wilson signed with the Cubs prior to the 1993 season as his career was winding down. He was 37 and had played in the majors since 1976. Wilson was a two-time All Star, two-time Silver Slugger winner, Gold Glove winner (1980), 1982 batting champion (.332), and was part of the 1985 World Series champion Kansas City Royals.

Wilson was simply old and washed when he came to the Cubs. In his 122 games in Chicago (1993-1994) he slashed .256/.298/.355 with one home run and a 77 OPS+. He was released in early 1994 and finished his MLB career with 2,207 hits in 2,154 games. Again, we had to give it to someone. Sorry, Willie.

Best: Rod Beck

Known to many as “Shooter”, Rod Beck remains to this day as one of the most popular Cubs relievers the team has ever had. After spending seven years in San Francisco, where he was a three-time All Star and racked up 199 saves, he signed with the Cubs prior to 1998. Beck was a massive part of that magical run to the postseason as he recorded a career-high 51 saves and pitched to a 3.02 ERA, 3.72 FIP, 1.3 WHIP, 81 strikeouts and 20 walks in 81 games. Those 81 appearances was the most by any National League reliever.

Beck recorded save #51 in game 163 at Wrigley Field when the Cubs defeated his former team, the Giants, in the tiebreaker for the Wild Card. While Beck struggled mightily in 1999 and was traded to Boston mid-season, 1998 will never be forgotten.

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HONORABLE MENTION: Randy Myers

We do have to mention one of the more underrated relievers the Cubs have had. Myers could easily be argued over Beck, and honestly based on numbers…probably should be. He signed as a free agent in 1993 and that year recorded a Cubs record 53 saves, which was first in the majors. Myers was an All-Star for the Cubs in 1994 and 1995 and finished his Cubs tenure with 112 saves, a 3.52 ERA and 177 strikeouts in 168 games. Beck gets the slight nod over him simply for the fact he was such a big part of the Cubs making only their third postseason since 1945 in 1998.

Worst: Jose Veras

Prior to the 2014 season the Cubs brought in veteran Jose Veras to be a backend bullpen piece. Veras had an overall solid career bouncing around teams, and had a stretch from 2010 – 2013 where he pitched to a 3.55 ERA, 3.66 FIP, 272 strikeouts and 1.3 WHIP in 266 appearances. He was coming off a career-best 3.02 ERA in 2013 with the Astros and Tigers. The Cubs gave him a one-year, $3.85 million deal with a club option in 2015.

His time in Chicago was brief and horrendous. In 12 appearances he blew two saves, pitched to an 8.10 ERA, 6.28 FIP and 1.7 WHIP. He was DFA’d in favor of Hector Rondon and was released in June. A few days after being released the Astros picked him up and he pitched to a 3.03 ERA and 1.3 WHIP in 34 games the rest of 2014.

Hopefully there will be more impactful free agents for the Cubs in the near future. This list certainly will spark some debate and stat-searching. There are probably guys that have been overlooked.