After All That, Did Jake Arrieta Make a Mistake In Negotiations With The Cubs?

The waiting is finally over. After suspecting it since a standing ovation sent him to the dugout after his masterful performance in Game 4 of the 2017 NLCS, it’s finally official. Jake Arrieta will not suit up for the Chicago Cubs in the foreseeable future. In what has been a historically disciplined free agent market, Jake signed a 3 year $75 million contract that will make him the next ace of the rebuilding Philadelphia Phillies.

I could go on a wandering soliloquy about how much Jake has meant to this franchise, this fanbase, and this city. How his excellence propelled our rebuild ahead of schedule. How he amazed us with a run of dominance the likes of which we probably won’t see again. Or how he created culture and inspired his teammates with his tireless work ethic and his naked photo shoots.

But the Chicago sports media landscape has been rife with tearful goodbye’s to Jake this past week. So I’ll go in a different direction. Looking at the contract he signed with Philadelphia, I can’t help but wonder if Jake made a big mistake this offseason.

He let Scott Boras whisper sweet nothings in his ear and went home with a sub-optimal contract. Not to say that $75 million is chump change. But Theo offered Jake $120 million over six years a few short weeks ago. The only way Arrieta exceeds $120 million of earnings in the next 6 years is if he signs for more than $45 million coming off his 35-year old season in 2020. Given GM’s increasing reluctance to dole out cash to veteran players, that scenario seems exceedingly unlikely.

I’m happy for Jake that he finally signed. And I’m even happier that he won’t be playing in St. Louis or Milwaukee. But I can’t help but feel like he was getting too much advice from the wrong people. His agent spent so much time selling his client to front offices, and I firmly believe he failed to understand the nature of this 2017-2018 free agent market.

It goes without saying that the Yu Darvish signing energized the fanbase. He’s our shiny new toy. But, at the end of the day, in their heart of hearts, most Cubs fans would rather have Jake than Yu. And after seeing how much it took to sign him, it feels like we should have kept him. It would have required Scott Boras and Jake to check their egos at the door and listen to what the market was screaming at them. And it didn’t happen.