The Top 10 Free Agent Signings in Chicago Cubs' History

While the signings of guys such as Alfonso Soriano and Milton Bradley are in the forefront of Cubs fan's minds, there have still been a number of great moves made by the front office throughout the years. This article will look at the ten best free agent signings in team history.

First, a few ground rules. I have only included signings made from the beginning of free agency in 1975 on, since prior to that the only free agent signings were amateur free agents, as the draft did not exist yet. Thus, everyone was a free agent to start their careers.

Also, I did not include amateur free agent signings after 1975, including the signings of foreign players such as Carlos Zambrano and Carlos Marmol, since they were not free agents in the traditional sense of the term.

What I have compiled is a list of the 10 best free agent signings that the Cubs have made as one would generally think of free agency, and while the list is far from impressive, each player made a significant contribution to the team and cemented their place in Cubs' history.

So with that, here are what I feel are the ten best free agent signings in Chicago Cubs history.

No. 10: Jim Edmonds

Date: May 14, 2008

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, when the Padres released the struggling Edmonds, who was hitting just .178 BA, 1 HR, 6 RBI through 26 games.

While it was certainly odd seeing the former Cardinals slugger don the Cubbie Blue at first, he immediately made the team better, as he and Reed Johnson formed a very productive platoon in center field the reminder of the season.

Edmonds finished with a line of .256 BA, 19 HR, 49 RBI in his time with the Cubs, and he did it while making about $300,000. This was hands down one of the best bargain signings in team history, and a big reason the team made the playoffs in 2008.

No. 9: Kevin Tapani

Date: Dec. 13, 1996

At the age of 34, and with an impressive 92-75 career record, the Cubs signed Tapani to provide some veteran leadership on what was a young pitching staff outside of Steve Trachsel.

After a 9-3 first season in which he was limited to just 13 starts, Tapani became the ace of the staff in 1998, winning a career best 19 games, despite a less than impressive 4.85 ERA. Along with Trachsel and Kerry Wood, the Cubs boasted one of the league's best rotations on their way to their first playoff berth since 1989.

Tapani earned an extension for his fine 1998 season, and finished his Cubs career with 51 wins in five seasons, a feat considering how bad the team was outside of that 1998 season.

No. 8: Mark DeRosa

Date: Nov. 14, 2006

After having a breakout year with the Rangers in 2006, in what was his first year as an everyday player, the Cubs took a chance on DeRosa, hoping that his career year was a sign of things to come and not simply a fluke. Lucky for the Cubs, DeRosa was just getting started.

While his offensive production was great, as he averaged .289 BA, 16 HR, 80 RBI including a career high 87 RBI in 2008, it was his versatility that made this such a good signing for the Cubs.

While he was signed to be the team's everyday second baseman, DeRosa played everywhere on the field besides catcher and center field during his two years with the team, as his versatility proved to be invaluable.

And while John Gaub and Jeff Stevens continue to shape up into two of the Cubs' best relief pitching prospects, the DeRosa trade is one that still doesn't sit well with most Cubs.

No. 7: Randy Myers

Date: Dec. 9, 1992

Already an established closer with 131 saves under his belt, the Cubs inked Myers to a three year contract and he quickly became one of the game's elite stoppers.

In his first season with the team, Myers saved a franchise record 53 games, as he notched a save in 63 percent of the team's wins that season.

He went on to save 112 games in his three seasons with the Cubs, leading the NL in that category twice while making a pair of All-Star appearances as well. He was one of the few bright spots on the mid-1990s Cubs.

No. 6: Moises Alou

Date: Dec. 19, 2001

Alou was exactly the middle of the order presence the Cubs needed to hit behind Sammy Sosa after watching the likes of Matt Stairs and Rondell White fill the cleanup role the previous season.

While his Cubs career started slowly, with only 15 HR and 61 RBI, he was very productive over the next two years of his contract, especially in 2004.

That year, Alou posted a .293 BA, 39 HR, 106 RBI line, as he set a career high for HR, made the All-Star team, and finished 14th in MVP voting.

Despite how successful his time in Chicago was, Alou will forever be remembered for his involvement in the dreaded Bartman incident. Curse you Steve Bartman.

No. 5: Ted Lilly

Date: Dec. 15, 2006

Depending on how much longer Lilly is a Cub and produces like he has, this signing could certainly move up this list.

In just three seasons with the team, Lilly has amassed a 44-26 record, including a 12-9 season last year that earned him a spot on the All-Star team as the Cubs lone representative.

He has quietly become one of the most consistent left handed pitchers in the game, and the Cubs will be anxiously awaiting his return this spring in hopes he is ready for Opening Day. A couple more solid seasons and this one could be at least No. 3.

No. 4: Dave Kingman

Date: Nov. 30, 1977

This move ranks so high on the list, not only because of Kingman's numbers, but because of the fact that it was the first big name free agent signing in team history.

That said, his power numbers were very impressive. In total, he launched 94 home runs in his short three years in Chicago, but 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, however, 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. All in all, not a bad signing.

No. 3: Ryan Dempster

Date: Jan. 21, 2004

After having Tommy John surgery in August of 2003, Dempster was released by the Reds that November. The Cubs decided to take a chance on the former All-Star starter, and signed him for one year, $300,000 contract.

Amazingly, he was back on the mound in a little under a year after the surgery, and he became one of the Cubs top relievers.

The Cubs brought him back for the 2005 season, and after making six starts, he returned to the bullpen where he took over the closer's role from LaTroy Hawkins. Three seasons and 87 saves later, he was back in the rotation and was a 17-game winner and All-Star.

Needless to say, Dempster has filled any and all roles for the Cubs since signing with the team, and taking a chance on him was one of the smarter moves the team has made.

No. 2: George Bell

Date: Dec. 6, 1990

On the surface, this was a solid signing, as Bell was no doubt one of the game's most feared sluggers and an asset to whatever lineup he was in.

His first and only season with the team was a successful one, as he hit .285 BA, 25 HR, 86 RBI and was named to the All-Star team.

However, it is what happened after that season that earns this signing the number two spot on this list. The Cubs, in rebuilding mode, decided to deal the slugger to the cross town White Sox, and in turn received setup man Ken Patterson and a scrawny little outfield prospect by the name of Sammy Sosa...and the rest is history.

No. 1: Andre Dawson

Date: Mar. 9, 1987

The story of how Dawson came play for the Cubs has become somewhat of a legend at this point, and regardless of whether or not it is true, it still makes for a great story.

After struggling to attract any offers in the off season, 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.