Cubs Could Create Full-Circle Moment By Signing Top Free Agent Pitcher

The Chicago Cubs have a chance to create a cool reunion with one of baseball's top free agents this winter.

Apr 3, 2019; Atlanta, GA, USA; Detailed view of Chicago Cubs hats and gloves in the dugout against the Atlanta Braves in the fifth inning at SunTrust Park. Mandatory Credit: Brett Davis-Imagn Images | Brett Davis-Imagn Images

The next couple of months should be a rollercoaster ride for Chicago Cubs fans.

As of November 2, the franchise has already had ten players (Caleb Thielbar, Drew Pomeranz, Kyle Tucker, Aaron Civale, Taylor Rogers, Ryan Brasier, Willi Castro, Carlos Santana, Michael Soroka and Brad Keller) elect free agency, which goes to show how different Chicago's roster might shake out by the time spring training rolls around.

The biggest story to follow is what happens with Kyle Tucker. He's expected to get the most lucrative contract in free agency this winter, with some estimates putting his projected contract in the range of $450 million. Most believe it's unlikely that the Cubs would be willing to offer him that much, so Chicago's fan base may need to prepare to receive news that Tucker has signed elsewhere relatively soon.

Chicago Cubs outfielder Kyle Tucker (30) | David Banks-Imagn Images

While that potential announcement is going to sting when it arrives, the good news is that the Cubs should be actively seeking people to replace Tucker in the lineup (albeit at a more affordable price) and also find ways to bolster their pitching staff.

One free agent starting pitcher that Chicago should keep an eye on is Dylan Cease, who spent the first five seasons of his MLB career on Chicago's South Side, with the White Sox, before getting traded to the San Diego Padres before the 2024 season.

How Dylan Cease's Cubs Connection Could Bring Him Back to Chicago

San Diego Padres starting pitcher Dylan Cease | David Frerker-Imagn Images

ESPN senior writer David Schoenfield clearly sees why Cease and the Cubs sense, as he called Chicago the top free agency fit for the 29-year-old pitcher in a November 3 article.

Schoenfield also noted that the Cubs' pursuit of Cease would make for a nice full-circle moment, given that Chicago originally drafted Cease in the sixth round of the 2014 MLB Draft while Cease was still in high school.

Cease then worked his way through the Cubs' minor league system for a few years before being a key part in a trade that brought former White Sox southpaw Jose Quintana to the Cubs a few weeks before the 2017 trade deadline.

Dylan Cease

Drafted by the Chicago Cubs in the 6th round of the 2014 MLB June Amateur Draft from Milton HS (Milton, GA). pic.twitter.com/3sL6GQiWFJ

— Scouting_Baseball (@scoutingbasebl) March 28, 2022

While a lot of things have happened since that 2014 MLB Draft, the Cubs' organization clearly once had a strong affinity for Cease. This could perhaps cause them to pinpoint him when deciding which pitchers to pursue in the coming months.

And maybe Cease still recalls his time in the Cubs' organization fondly, and would be more than willing to reunite with his former franchise this offseason.

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