McGraw: A little patience by Cubs might have led to better results

Don't be sad it's over, be glad it happened.

That's certainly a line the Cubs will be selling to fans as they move past the World Series era and onto a rebuild or reload or whatever they plan on calling it.

Was the great sell-off inevitable? What could the Cubs have done differently to avoid last week's demolition day? Let's break down what went wrong.

Jose Quintana trade

This happened on July 13, 2017. Rankings vary, but the Cubs essentially sent their best position prospect, Eloy Jimenez, and best pitching prospect, Dylan Cease, to the White Sox for left-handed starter Jose Quintana, who was attractive because he was signed through 2020.

Quintana did fine, won 13 games in 2018 and '19, and had a nice start in the 2017 division series against Washington. Obviously, this addition did not push the Cubs to another World Series. Team president Jed Hoyer talked about the process when he met with reporters on a Zoom call last week.

“We threw a lot of prospects into a lot of trades over the last five years to try to win,” Hoyer said. “We were really aggressive during this window to try to be as good a team as possible. And I'm proud of that. At the deadline, when you're winning, you should be aggressive and in the winter you should be aggressive and we were, and I don't think we left anything on the field as far as aggressiveness to try to win.”

It's always easier in hindsight to dissect these moves, but hindsight wasn't required to follow the example of Hoyer and Theo Epstein's former team, the Boston Red Sox.

The Red Sox had already won three World Series titles at that point by using a longer-term approach. They'd win one, maybe take a step back, then win again with a mix of the same stars and some new blood.

Last year, Jimenez, 24, would have led the Cubs in every offensive category. This year, Cease, 25, would be their second-best starter.

A better approach would have been to look at the Cubs' young nucleus and, rather than sacrificing the future to win in 2017, setting a goal of getting back to the World Series in '20 or '21. Along the way, maybe they should have traded one of the key guys and extended the other two. Maybe they could have retooled the roster to include Nick Castellanos.

But what ended up happening was the Cubs took a 10-year window and turned it into a three-year window.

Jason Heyward's contract

Obviously, Heyward contributed to the World Series title, but it's tough when the highest-paid player is not one of a team's 10 best players, which has been the case for most of the last six years. And Heyward's deal runs for two more seasons at $22 million per.

Did this contract have an effect on the missing extensions for Kris Bryant, Javy Baez and Anthony Rizzo? Heyward made as much as $28 million in the early years of this deal, but the Cubs likely offered less to the other guys.

Did the Cubs really need to include those last two years on Heyward's offer? It would have been nice if this deal ended when Bryant, Baez and Rizzo were hitting free agency. The Red Sox were able to unload David Price's bad contract by including him in the Mookie Betts trade with the Dodgers, so there's another idea.

Lack of player improvement

Let's face it: The last few years of Cubs baseball featured plenty of swing-and-miss or grounding into the shift. In the biggest moments late in the season, the offense failed.

The Cubs never adequately replaced Dexter Fowler and Ben Zobrist, but the success of the Cubs' hitters shouldn't have depended on having a healthy Matt Duffy somewhere in the lineup.

Breaking the bank to rescue a fourth-place team was not in the cards for the Cubs. If this group had made better adjustments at the plate, it might not have come to this.

Twittter: @McGrawDHSports

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