MLB Free Agency: Chicago Cubs Best and Worst Signing at Each Position

The Chicago Cubs are entering a new era of their franchise, as they are finally starting to get out from under some of their bad contracts and now have a new front office tandem in Jed Hoyer and Theo Epstein.

Those two will be counted on to make some wise decisions to get the team back into the postseason, and that will start with what they do in free agency this coming winter.

Through the years, the Cubs have had their fair share of success stories, as well as colossal busts, when it comes to their free agency endeavors.

So here is a look at the Cubs' best and worst free agent signing at each position, dating back to the start of free agency in the early 1970s.

Catcher

Best: Joe Girardi (Three-Year, $5.5 Million)

Heading into the 2000 season, the Cubs signed the then 35-year-old veteran Girardi to serve as their starting catcher. He was joined by Todd Hundley the following season and the two platooned.

While his numbers were never great, Girardi did make the All-Star team in 2000 (.278 BA, 6 HR, 40 RBI) and was more or less another coach on the field during his second go-around with the Cubs. 

Worst: Todd Hundley (Four-Year, $23.5 Million)

When the Cubs added Hundley prior to the 2001 season, it came with a good deal of fanfare, as he was coming off a 24 HR, 70 RBI season and was the son of former Cubs catcher Randy Hundley, so it was a homecoming of sorts.

However, once play started, he couldn't have been a bigger flop, as he hit a combined .199 BA over his two seasons with the team as he struck out once every three at bats. The Cubs did manage to flip him to the Dodgers for Eric Karros and Mark Grudzielanek before the start of the third year of the deal.

First Base

Best: Carlos Pena (One-Year, $10 Million)

With homegrown talent Mark Grace and trade acquisitions Bill Buckner, Leon Durham and Derrek Lee manning first base for a combined 31 seasons, there were not many choices for a free agent signing at first base.

While his average was troublingly low once again, Pena bounced back from a horrible 2010 season and gave the Cubs some legitimate left-handed power in the middle of their lineup last season, as he hit 28 HR with 80 RBI.

Worst: John Mabry (One-Year, $1.075 Million)

One of the top pinch-hitters in all of baseball, the Cubs signed Mabry to fill out their bench for the 2006 season. However, when Derrek Lee broke his wrist, Mabry was forced into an everyday role.

He responded by hitting a dismal .205 BA, 5 HR, 25 RBI, and the Cubs eventually traded for Phil Nevin to take over as the everyday first baseman.

Second Base

Best: Mark DeRosa (Three-Year, $13 Million)

Coming off of a career year with the Texas Rangers, the Cubs inked DeRosa prior to the 2007 season. Many skeptics believed that his career best season would be the exception rather than the rule moving forward, but he put up similar numbers over the next two seasons.

Not only that, but he was one of the most versatile defenders in all of baseball, and when the Cubs dealt him to the Indians, it was believed to be as a precursor to acquiring Jake Peavy. That did not come to pass, and that trade stands as one that left a bad taste in Cubs fans' mouths.

Worst: Neifi Perez (Two-Year, $3.5 Million)

The Cubs have done fairly well in their history with second baseman, but the fact is that most of their second basemen in the past 40 years were either acquired through trade or named Ryne Sandberg, so finding a bad signing was somewhat tough.

In the end, I settled on Perez, although he played more games at shortstop subbing for the injured Nomar Garicaparra than he did at second base. The definition of a light-hitting, slick-fielding utility player, Perez had no business being in the starting lineup, let alone playing 154 games as he did in 2005.

Shortstop

Best: Ricky Gutierrez (Two-Year, $5.9 Million)

A utility player during his time with the Astros, the Cubs took a chance when they signed Gutierrez to be their starting entering the 2000 season, but he was steady offensively and in the field during his two years with the team.

He hit a combined .284 BA, 21 HR, 122 RBI, 149 R in his two seasons in Chicago, with a total WAR of 3.3, as he was one of the better shortstops in the National League.

Worst: Jeff Blauser (Two-Year, $8.2 Million)

A household name of sorts after appearing in the postseason year in and year out as the starting shortstop of the Atlanta Braves, Blauser picked the perfect time to have the best season of his career, when he hit .308 BA, 17 HR, 70 RBI at the age of 31 in his final season with the Braves.

Looking to fill a hole at shortstop, the Cubs signed Blauser for way too much money and paid the price when he crashed back down to Earth, and he crashed hard. In his first season with the team, he hit just .219 over 361 at bats before being replaced by career utility man Jose Hernandez in the starting lineup. He was not much better the next year, and retired following the 1999 season.

Third Base

Best: Vance Law (Two-Year, $800,000)

Coming off of a productive season with the Expos as a utility player in 1987, the Cubs signed Law to be their everyday third baseman, inking him to a two-year deal.

In his first season in Chicago, he was very good, hitting .293 BA, 11 HR, 78 RBI and making the NL All-Star team. His stats fell off the following season, but still represented one of the better Cubs third basemen between Ron Santo and Aramis Ramirez.

Worst: Willie Greene (One-Year, $395,000)

As much of a revolving door as the third base position was following Ron Santo's retirement, the Cubs acquired the majority of their one-year wonders via trade, and one of the only free agent signings to be handed the starting job outright was Greene.

After hitting 26 home runs in 1997, Greene's career tapered off greatly, and by the time the Cubs signed him for the 2000 season, the 28-year-old didn't have much left, as he hit just .201 BA, 10 HR, 37 RBI as the team's primary third baseman.

Special Mention: Gary Gaetti

After being released by the Cardinals late in 1998, the Cubs signed Gaetti as a free agent, and he proceeded to hit .320 BA, 8 HR, 27 RBI in just over a month of action to help the team to the postseason.

However, he was brought back the following season on a one-year, $2 million deal, and he hit just .204 BA, 9 HR, 46 RBI. So in essence, he could fill both spots on this list, but instead, we will give him special mention.

Left Field

Best: Dave Kingman (Three-Year, $825,000)

The Cubs' first big free agent signing, Kingman was a slugger in every sense of the word. In total, he launched 94 home runs in his short three years in Chicago, and that was enough to make him a fan favorite and to carve his place in team history.

His 1979 season was by far his best, as he led the NL with a career-high 48 home runs, while also hitting a career best .288 and driving in 115. That netted him an 11th place MVP finish and the first of two All-Star appearances with the North Siders.

Worst: Alfonso Soriano (Eight-Year, $136 Million)

Coming off of a 46 HR-41 SB season with the Nationals, the Cubs inked Alfonso Soriano to one of the richest deals in baseball history.

He then immediately lost the ability to run the bases and still refuses to lay off of a breaking ball low and away. So far through five years he has put up an average season of .266 BA, 26 HR, 73 RBI which in no way, shape or form is worth $18 million per season.

Honorable Mention: Moises Alou

Center Field

Best: Jim Edmonds (One-Year, $300,000)

With Felix Pie quickly proving he could not handle the everyday center field role, and Kosuke Fukudome failing to deliver the type of run production the Cubs needed in the fifth spot in the lineup, the Cubs were faced with a pair of issues early in the 2008 season.

Then, the answer to both problems fell in their lap. The Padres released the struggling Jim Edmonds, who then proceeded to hit .256 BA, 19 HR, 49 RBI after joining the Cubs while forming a fantastic platoon with Reed Johnson.

Worst: Jacque Jones (Three-Year, $16 Million)

Coming off of a solid run with the Twins, the Cubs signed Jacque Jones to be their starting right fielder heading into the 2006 season, and he responded with a .285 BA, 27 HR, 81 RBI season. The next season, however, he fell off badly and was benched before working his way back into the starting lineup in centerfield, yet he would end the season with just five home runs. He was traded before the start of the third season, as the Cubs cut their losses at that point.

Right Field

Best: Andre Dawson (One-Year, $750,000)

After struggling to attract any offers in the offseason, largely because of collusion on the part of the owners that season, it is said that Dawson and his agent came to Cubs owner Dallas Green with a signed, blank contract and told him he would play for whatever the Cubs offered him.

That ended up being $500,000, with a $250,000 bonus if he managed to started the All-Star game and won the MVP. And wouldn't you know it, that is exactly what he did.

Despite playing for a 76-85, last place team that season, Dawson's stat line of .287 BA, 49 HR, 137 RBI was enough for him to be named MVP. He led the league in HR and RBI while taking home the Gold Glove and Silver Slugger as well.

Dawson went on to five more productive seasons with the Cubs after his MVP 1987 season, and he goes down as the best free agent signing in team history.

Worst: Milton Bradley (Three-Year, $30 Million)

Coming off of a career year in which he hit .321 BA, 22 HR, 77 RBI and led the AL with a .436 on-base percentage as a member of the Rangers, the Cubs signed Bradley hoping to break up their many right-handed bats.

He struggled mightily, though, hitting .257 BA, 12 HR, 40 RBI and eventually getting kicked off the team for the remainder of the season for his negative impact on the clubhouse. The Cubs then dealt him to the Mariners for Carlos Silva in a bad-for-bad trade.

Dishonorable Mention: Kosuke Fukudome, Jeromy Burnitz

Starting Pitcher

Best: Kevin Tapani (Three-Year, $11.25 Million)

Coming off a 13-10 season with the White Sox, the Cubs scooped up Tapani for a bargain considering he would be the ace of their 1998 playoff team.

After a solid 9-3 season in 1997, Tapani apparently found the fountain of youth, as he went 19-9 in 1998, having his best season at the age of 34. The team then gave him a two-year extension that did not yield as good of results, but the original deal was a fantastic one.

Worst: Danny Jackson (Four-Year, $10.55 Million)

Just two seasons removed from a 23-8 season with the Reds, the Cubs signed Jackson with expectations of him being the staff ace. Swing and a miss on that one.

In his first season with the team, he went a paltry 1-5 with a 6.75 ERA in 14 starts and three relief appearances. The next season was more of the same. as he went 4-9 in 19 starts before being dealt to the Pirates for third basemen Steve Buechele.

Relief Pitcher

Best: Rod Beck (One-Year, $3.6 Million)

Beck played a huge role in the success of the 1998 team, saving 51 games and leading the NL in appearances with 81, as he had the best season of his impressive career.

This signing is sullied a bit by the fact that the Cubs gave him a three-year, $13.5 million contract extension after the 1998 season. However, the Cubs only ended up paying him $5.5 million for his poor 1999 season, as they dealt him to the Red Sox for Mark Guthrie, a midseason move that dumped his contract in the process.

Worst: LaTroy Hawkins (Three-Year, $11 Million)

On the surface, Hawkins' first season with the Cubs in 2004 looks great. He had a 2.63 ERA in 77 appearances and saved 25 games after taking over the closer's job from Joe Borowski early in the season.

However, he also blew nine saves, including two huge ones in late September that were a big part of a collapse that cost the team the Wild Card.

The 2005 season was more of the same, as he had four losses and was 4-of-7 in save opportunities, and after 21 appearances that season, the Cubs had finally seen enough, and, to the joy of fans everywhere, traded him to the Giants for David Aardsma and Jerome Williams.