Cubs have extended just six homegrown players in last 40 years

Last night, my wife and I went out to dinner – and proved that even with an 8:30 reservation, you can, indeed, still be in bed and asleep by 10. The downside of that scenario is that I woke up by 5 this morning, so I pulled up Twitter and one of the first things I saw on my feed was this.

So right then and there, my mind started racing and I knew going back to bed just wasn’t an option. This fact really changed how I looked at the Cubs’ lack of extensions for the 2016 World Series-winning core; at least in some regards.

Now, when you’re the ownership group that got a franchise that hadn’t won in over a century to the top of the proverbial mountain, one would think maybe some of those past patterns may be cast to the side. But, as we all know, that hasn’t proven to be the case when it comes to the Ricketts family and extensions for homegrown guys.

(Also, as has been pointed out repeatedly on Twitter, until recently, the Cubs, frankly, were just not great at developing homegrown talent – which undoubtedly plays a huge role here).

The lone exception being David Bote, who inked a five-year, $15 million extension that covers 2020-2024 with a pair of team options that, assuming he’s still on the roster, will surely be declined by the front office. Why? Because he’s only once been a league average hitter (by wRC+ and/or OPS+) once in his career and has hit just 200/.285/.353 since the start of 2020.

Prior to Bote, the Cubs gave Starlin Castro, who once looked like a franchise cornerstone and a guy with an outside shot at 3,000 knocks, a seven-year, $60 million extension. He didn’t even finish out that extension with the Cubs, with Chicago trading him to the Yankees following the 2015 campaign.

A pair of fan favorite Cubs pitchers and some icons from yesteryear

Carlos Zambrano fetched nearly $100 million from the Cubs in the form of a five-year, $91.5 million pact, late during the 2007 season as a 26-year-old. He earned the third All-Star selection of his career and picked up a pair of Silver Sluggers during the next four years, before the new Theo Epstein-led regime sent him to the Marlins in exchange for Chris Volstad.

Three years prior, the Cubs locked up former NL Rookie of the Year Kerry Wood, giving the right-hander a three-year extension on the heels of a dominant 2003 campaign that saw Chicago get to the brink of its first World Series since 1945. That year, Wood led the league with 266 strikeouts en route to the first All-Star selection of his career. We all had visions of where Wood, paired with Mark Prior, would lead the franchise in years to come which, well, turned out to be nowhere.

Still, who could forget Wood’s final go-round with the Cubs, walking off the mound after notching a strikeout against the White Sox, with his son leaping into his arms? What a moment.

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Three-year pacts with Mark Grace and Shawon Dunston round out this list, just reinforcing the lack of A) extensions with homegrown talents, the entire point of this piece and B) the lack of homegrown guys the organization successfully developed and turned into quality big league players over the last 40 years. Let’s hope we see more success with this next wave of Cubs prospects.