With Yu Darvish signing a six-year deal with the Chicago Cubs, former Cub Jake Arrieta is the only ace left on the market this winter.

A move that had been building for seemingly the entire offseason finally went down last weekend. Free-agent right-hander Yu Darvish and the Chicago Cubs agreed to terms on a six-year contract worth $126 million. It’s quite a lengthy contract for a pitcher who has already had Tommy John, and becomes the most expensive deal inked by a free agent who had already had the surgery (Stephen Strasburg signed a $175-million extension with the Washington Nationals, but never tested the open market).

Darvish to the Cubs makes sense on multiple levels. The team needed an ace to lead a rotation that features Jon Lester, Kyle Hendricks, Jose Quintana and Tyler Chatwood in slots two through four. They are all solid and established veterans, but none are quite cut out to take the ball in Game 1 of a playoff series.

It’s not surprising that the Cubs made an aggressive play to sign a front-line starter to their rotation. The wheeling-and-dealing winter of the Milwaukee Brewers all but guaranteed they would make a major move to keep pace. What is very interesting is that the team never even engaged Jake Arrieta or agent Scott Boras at any point. Their focus shifted to Darvish immediately after missing out on Shohei Ohtani.

That can’t be a good sign for Arrieta and Boras. The Cubs have gotten to look at the 31-year-old for the last five years. They’ve taken him from a bust with the Baltimore Orioles to one of the best pitchers in baseball. Along the way, he strung together one of the most dominant stretches in MLB history, won a Cy Young, threw two no-hitters and was the winning pitcher in two games of the 2016 World Series.

Arrieta did just about everything in his power to show the Cubs he was worth a long-term deal, but began struggling with command in the second half of 2016 and all of last season. But even with his issues, Arrieta had led the major leagues in hits per nine two years in a row before seeing a spike up to eight per nine in 2017 with a massive increase in home runs allowed. That hiccup weighed more heavily on Theo Epstein’s mind than the established track record that saw Arrieta go 68-31 with a 2.73 ERA and five more playoff wins with a 3.08 ERA in nine starts.

In five years with the Cubs, Arrieta was never willing to engage on extension talks before free agency — and why would he? Boras clients never sign extensions. This is Arrieta’s one shot at a nine-figure deal, and he needed to get it right.

In this brave, new MLB world where owners and GMs refuse to give in and open their checkbooks, Jake Arrieta may have to continue waiting if he wants to find the best deal. Removing the Cubs from the equation will no doubt make that more difficult. Their hesitancy to even make an offer will also lead to questions over his long-term health. Arrieta has never had a major surgery but was limited to only 30 starts last year by lower-body injuries.

Darvish labored through the worst season of his career in 2017 and then imploded in the World Series. The Cubs still saw him as the better bet to lead their rotation for the next six years. For the teams remaining in on Arrieta, that should be cause for concern. The Brewers, Minnesota Twins and possibly the Los Angeles Angels or St. Louis Cardinals remain as the best potential landing spots for the free agent. None of them have such a pressing need in the rotation to jump first on Arrieta or cave to whatever Boras demands. The Brewers and Twins have never signed a free agent to a nine-figure deal, while the Cards and Angels have already had busy offseasons.

The market just didn’t play itself out in Jake Arrieta’s favor, but he is hardly alone. Fellow Boras clients Eric Hosmer and Mike Moustakas still need deals. Mid-tier starters like Alex Cobb and Lance Lynn are also unsigned. Eventually, things will break. Unfortunately for Arrieta, the Cubs had two choices and they went away from their own player. A nine-figure deal will still come his way, but it might require a compromise on years (a pillow deal seems hugely unlikely, but don’t rule it out) or annual value. Scott Boras almost always comes out on top when he matches wits against MLB front offices, but he’s got his work cut out for him now more than ever as he attempts to find a home for Jake Arrieta.

 



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