Ranking the top 5 free agent signings in Chicago Cubs history

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.