Ranking the top 5 free agent signings in Chicago Cubs history

With MLB Network waging war on one of the most reputable reporters in the game, no offseason moves being made because of the ongoing lockout and a complete and utter lack of Chicago Cubs-related news to fill my day, I’ve taken to re-reading my favorite Cubs books, watching a lot of old Cubs games and looking back at my three decades of fandom.

The big news prior to the lockout? The Cubs look like a legitimate contender for the top free agent in this year’s class in Carlos Correa. The former AL Rookie of the Year, should he come to the North Side, has the potential to wind up on this very list someday: the top 5 free agent signings in Chicago Cubs history. Let’s get started.

5 best free agent signings in Chicago Cubs history: #5 – Moises Alou

I recently looked back on Moises Alou’s absolutely bonkers 2004 season when, at age thirty-seven, he decided to go out and turn in one of the best single-season performances of his 17-year big league career.

Coming off one of the most heartbreaking scenes in Cubs history the prior October, expectations were high heading into ’04. Things didn’t pan out – but that’s not because of Alou. He put the finishing touches on his Cubs career in a major way, smashing a career-high 39 home runs and driving in106 runs.

All told, during the span of his three-year stint in Chicago, Alou did everything asked of him and then some. The veteran outfielder slashed .283/.353/.484, driving in 258 runs and averaging 25 home runs and 86 RBI per year. And let’s not forget. He was a monster during that 2003 run, with a 1.074 OPS in the NLDS and a .907 mark against the Marlins.

5 best free agent signings in Chicago Cubs history: #4 – Ben Zobrist

This isn’t the last member of the 2016 World Series championship-winning team we’ll see on this list, but let’s first give Ben Zobrist his due.

Hot off a World Series title with the Kansas City Royals the year prior, Zobrist inked a four-year, $56 million with Chicago, bringing a versatile veteran presence to what was still one of the youngest (and most promising) teams in the league.

In his first season with the Cubs, he got on base nearly 39 percent of the time, earned the third All-Star selection of his career and, just for good measure, brought home World Series MVP honors after hitting .357 and driving in the go-ahead run late in Game 7.

His time in Chicago ended rather unceremoniously due to off-the-field personal matters between he and his then-wife. His salary, freed up by his decision, wound up going to Craig Kimbrel who, in turn, was flipped for Nick Madrigal and Codi Heuer this past summer.

But that’s not what you should remember Zo for. In his three-plus years here, he brought an old-school vibe and backed it up with his performance. He got on at a .362 clip, played all over the diamond – and did it all in the back half of his thirties. This guy was – and is – a Cubs legend.

5 best free agent signings in Chicago Cubs history: #3 – Ryan Dempster

Nearly four years ago, the Cubs held competitions around the city with the chance for individuals to win tickets to games ahead of the 2018 season. Given I worked two blocks away, on my lunch I headed over and there was Ryan Dempster, leading the charge.

Now a presence on Marquee Network, Dempster still plays a large role in the franchise and its identity – but for our purposes here, we’re going to focus on his work on the mound from 2004 to 2012, when he thrived as both a closer and a starter on the North Side.

During that stretch at different points, he led the league in games finished and games started. He racked up 87 saves and also had a 17-win 2008 season in which he received down-ballot Cy Young votes. Upon transitioning to a starter from the bullpen, all he did was eclipse 200 innings for four straight seasons, working to a respectable 3.81 ERA in the process.

The Cubs signed him in free agency twice – and the results speak for themselves. Better yet, at the tail end of his time with the team, he was traded to Texas in the deal that netted Kyle Hendricks. We all know how that career has gone and what he’s accomplished to this point. This was a huge win.

5 best free agent signings in Chicago Cubs history: #2 – Andre Dawson

You can’t have this list and not have Andre ‘The Hawk’ Dawson at or near the top of it. The main thing separating Dawson from the top spot is something that he, like so many other Cubs icons, failed to bring home: that World Series ring.

But that doesn’t take anything away from Dawson’s time with Chicago. The veteran, thankful to be free from the shoddy playing surface up in Montreal and the injuries that accompanied it, came to Wrigley in 1987 and immediately proved he had plenty left in the tank, hitting 49 home runs and driving in 137 en route to NL MVP honors.

That marked the first of five-straight All-Star appearances for Dawson, who also brought home a Silver Slugger and a pair of Gold Gloves during that run. Although he never replicated those MVP-caliber numbers, he was still a major factor on those Cubs teams in the late 80s and early 90s.

Dawson’s Cubs career included 174 home runs (and, with it, the seventh-highest slugging percentage in franchise history) and, at the end of his 21-year career in Major League Baseball, a plaque among baseball’s immortals in Cooperstown.