{"numbering":"asc","slides":[{"index":1,"title":"10. CF Jim Edmonds — one year, league minimum (2008)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/jim_edmonds.jpg","caption":"

Surprised to see the longtime Cardinal here? The Cubs signed Edmonds in May 2008 after receiving little center field production to start the season — .245/.324/.315 with a 67 wRC+ in 66 games. Edmonds’ own early-season struggles led to his release by the Padres, but he turned things around on the North Side.

Playing in a platoon with Reed Johnson, Edmonds hit .256/.369/.568 (.937 OPS) in 85 games with the Cubs, smacking 19 home runs. The season ended with an NLDS loss to the Dodgers, but taking a flier on a longtime rival addressed a weak spot for the Cubs.

"},{"index":3,"title":"9. RP Randy Myers — three years, $11 million (1993-95)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/wrigley-field-4.11_1.png","caption":"

Myers enjoyed three good years as the Cubs' closer, posting a 3.52 ERA and 1.31 WHIP while converting 112 saves (in 129 tries). He led all closers in saves (53) in 1993, earning both NL Cy Young and MVP award votes. His 38 conversions led the NL in 1995.

Myers is remembered in Chicago for two notable blown saves. He surrendered a game-tying single on Aug. 15, 1993, "Randy Myers poster day," and hundreds of fans threw their posters onto the field to express their disappointment.

On Sept. 28, 1995, a fan ran onto the field to confront Myers after he surrendered a go-ahead two-run homer against the Astros. The Cubs were fighting for an NL wild-card spot, and while they won in extra innings, they missed the playoffs.

Myers earned two All-Star selections as a Cub (1994-95) before moving on to the Orioles for the 1996 season.

"},{"index":5,"title":"8. UTIL Mark DeRosa — three years, $13 million (2007-08)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/derosa_otd_2008.jpg","caption":"

DeRosa joined the Cubs in 2007 after a career year with the Rangers a season prior. The veteran was a swiss army knife on back-to-back Cubs postseason teams, playing every position except pitcher, catcher and center field.

DeRosa hit .289/.373/.451 with a 113 wRC+ as a Cub. He drilled a then-career-high 21 home runs in 2008 and was one of the few bright spots in that infamous 2008 NLDS — going 4-for-12 in three games.

The Cubs traded DeRosa to the Indians on New Year’s Eve 2008, a deal which netted them then-prospect Chris Archer. They later shipped Archer to Joe Maddon’s Rays in 2011 in exchange for starter Matt Garza.

"},{"index":7,"title":"7. LF Dave Kingman — five years, $1.4 million (1978-80)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/davekingman.jpg","caption":"

Kingman provided immediate thump to the middle of the Cubs’ lineup. He hit 28 home runs in 1978, and for an encore led MLB in long balls (48) in 1979. He slashed .288/.343/.613 that season, easily the best of his 16-year career.

Kingman played a lead role in one of the most memorable games in Cubs history — a 23-22 loss to the Phillies on May 17, 1979. He went 3-for-6 with 6 RBIs that day, all three hits leaving the ballpark. The third was an absolute bomb.

After back-to-back All-Star game appearances, the Cubs traded Kingman to the Mets in February 1981.

"},{"index":9,"title":"6. SP Ted Lilly — four years, $40 million (2007-10)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/tedlillyap.jpg","caption":"

Remember him? Lilly joined the Cubs the same offseason as DeRosa and helped the Cubs go worst-to-first in the NL Central in 2007. The soft-tossing lefty was a steady presence on the mound, sporting a 47-34 record, 3.70 ERA and 1.14 WHIP in 3+ seasons in Chicago.

Some of the best seasons of Lilly’s career came in a Cubs uniform. He posted career bests in innings (207 — 2007), wins (17 — 2008) and ERA (3.10 — 2009), making his second and final career All-Star appearance in 2009.

Lilly compiled a 3.69 ERA through 18 starts in 2010, one of which saw him take a no-hitter into the ninth inning against the White Sox at Wrigley Field. The Cubs traded him and infielder Ryan Theriot to the Dodgers ahead of the July 31 deadline.

"},{"index":11,"title":"5. UTIL Ben Zobrist — four years, $56 million (2016-19)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/zobrist.jpg","caption":"

I mean, Zobrist delivered the biggest hit in Cubs history. That alone earns the guy a spot on this list.

The Cubs signed Zobrist for his contact-oriented bat after their offense shut down in the 2015 NLCS. His 2016 Game 7 heroics aside, Zobrist was a respected presence in the Cubs’ clubhouse, hitting .269 with a .362 OBP in four seasons.

Zobrist slotted anywhere from leadoff to fourth in the lineup. The Cubs signed him to play second base, but he moved to the outfield frequently, opening up numerous lineup possibilities.

Championship teams need steady veterans, and Zobrist was exactly that during his time in Chicago.

"},{"index":13,"title":"4. SP/RP Ryan Dempster — one-year, $500K (2004-12)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/ryan-dempster-0208.jpg","caption":"

Dempster’s longevity in Chicago alone warrants a Top 5 spot on this list. The Cubs signed him in January 2004 amid his recovery from Tommy John surgery, a pact that evolved into a eight-and-a-half-year relationship.

Dempster emerged as the Cubs' closer, racking up 87 saves through 2007. He moved into the rotation in 2008, winning 17 games to go along with a 2.96 ERA — making his second All-Star game.

Dempster finished his Cubs career 67-66 with a 3.74 ERA and 1.32 WHIP in 374 games (154 starts). The Cubs shipped him to the Rangers at the 2012 deadline, landing a prospect named Kyle Hendricks. The rest, as they say, is history.

"},{"index":15,"title":"3. LF Moises Alou — three years, $27 million (2002-04)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/alou-ap-2003.jpg","caption":"

Alou could be higher on this list, but third feels about right. He spent three seasons on the North Side, beefing up the middle of the order alongside Sammy Sosa.

Alou slashed .283/.353/.484 with 76 home runs as a Cub, 39 during his 2004 All-Star season. He was a force at the plate in the 2003 postseason, hitting .388 with a .423 OBP in 12 games. According to FanGraphs, his performance in Chicago was worth $44.8 million, making his actual contract a relative bargain.

Alou is largely remembered in Chicago for being involved in the Steve Bartman incident, which is unfortunate. No doubt we'd look back on his Cubs tenure differently had they reached the 2003 World Series.

"},{"index":17,"title":"2. RF Andre Dawson — one year, $650K (1987-92)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/andre_dawson_cubs_slide.jpg","caption":"

It’s funny how one of the Cubs’ all-time best free agent signings is one they hesitated to make.

Dawson remained unsigned into March 1987 due to collusion by league owners over signing free agents. Then 32, his résumé featured six Gold Gloves and three All-Star appearances. He rejected a low-ball offer from the Expos, whom he played for the previous 11 seasons.

Expressing a desire to play for the Cubs, Dawson and his agent, Dick Moss, presented GM Dallas Green with a blank contract to fill out. The Cubs obliged, and Dawson, free from Montreal’s AstroTurf — which left him with chronic knee pain — delivered.

Dawson won the 1987 NL MVP award behind 49 home runs (t-No. 1 in MLB) and 137 RBIs (No. 1). He signed an extension in spring 1988 and remained a Cub through 1992, slashing .285/.327/.507 with 174 homers and 587 RBIs in six seasons.

All that from a guy the Cubs almost didn't sign. Go figure.

"},{"index":19,"title":"1. SP Jon Lester — six years, $155 million (2015-present)","image":"https://www.nbcsports.com/sites/rsnunited/files/archive/assets_media_gallery/chicago/2020/03/24/lester-806.jpg","caption":"

This move turned the tide, legitimizing Theo Epstein’s plan to build the Cubs into annual contenders. Lester signed what was then the largest deal in team history, joining a last place club on the verge of a breakout behind an elite farm system.

In signing Lester, the Cubs gained an ace for their rotation, a battle-tested veteran and two-time World Series champion. His experience and leadership has proved to be invaluable to the Cubs' clubhouse.

In five seasons, Lester is 74-41 with a 3.54 ERA and 1.24 WHIP. He’s made two All-Star appearances (2016, ’18); he’s been rock solid in the postseason, posting a 2.44 ERA in 12 games — two coming in relief.

Without Lester, there is no 2016 championship. He changed the Cubs' culture, and not only is the best free agent signing in team history, but one of the best in Chicago sports history as well.

"}]}

Cubs' best 10 free agent signings of all time