Ranking the top 5 free agent signings in Chicago Cubs history

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.

5 best free agent signings in Chicago Cubs history: #1 – Jon Lester

Look, if you made it this far, odds are you know how this ends. With Big Jon fist pumping as he stomps off the mound in Cleveland five-plus years ago, on the brink of doing what so many others had tried and failed to do over the last 108 years.

Jon Lester changed everything when he came to the Chicago Cubs prior to the 2015 season. He, along with the hiring of Joe Maddon as manager, put an end to the acceptance of losing that had long taken hold of the franchise and set a new tone forward.

Lester flirted with 20 wins not once, but twice, with the Cubs – winning 19 during his NL Cy Young runner-up 2016 season then 18 two years later. A pair of All-Star appearances, a bulldog mentality that permeated throughout the dugout and clubhouse when he started and some of the grittiest pitching performances I’ve seen as a Cubs fan.

When you not only come to a team to change the culture and expectations, but deliver on said change, you earn a special place in the history books. Lester helped end not one, but two, of the most infamous title droughts in sports – and his exploits in Chicago won’t soon be forgotten.