Do I know for sure that the Padres absolutely overpaid for Manny Machado? Or that the Phillies will certainly regret the size and scope of the contract they gave to Bryce Harper? No, of course not.
But I do know that historically speaking, most of the baseball contracts of the 10-year, 9-figure variety that teams have handed out were mistakes for the teams that proffered them. As reference, here is a list of the five players in in baseball history who had signed a deal worth $240 million or more prior to this off-season:
Notice a trend? Stanton, traded. A-Rod: first deal, traded, second deal, released. Cano, just traded. Doesn't seem like a ringing endorsement on behalf of management.
What about the other two still with the teams that signed them? One could argue that after a slow start, Pujols has been a good player for the Angels. But maybe Anaheim thought they were paying $24 million annually for the All-Star with 11 top-five MVP finishes, including three trophies, instead of the solid contributor who managed to crack the top 20 only twice since. Less could be said for Cabrera, who has struggled with injuries and age since signing that bank-breaking extension in 2014.
Yet a mega-deal's impact can extend beyond just on-field performance. For that, we can look to Zack Greinke.
Even with the enormous payouts to Harper and Machado, Greinke still owns the title as highest-paid player: his six-year, $206.5 million contract with the Diamondbacks works out to $34.4 million per year. Relatively speaking, he's been worth it: Greinke has a 45-25 record and a 3.53 E.R.A for Arizona over three seasons. But that doesn't tell the real story.
Arizona's gamble on Greinke -- an ace leading an ascendant team into post-season glory -- hasn't panned out. Essentially admitting defeat this off-season, the D-backs shipped All-Star Paul Goldschmidt to St. Louis and lost A.J. Pollock and Patrick Corbin to free agency. That has left the team's payroll "comically top-heavy":
Greinke will make nearly five times the salary of any of his teammates; the next highest-paid Diamondback is outfielder David Peralta, at $7 million. Hall said the Greinke contract had made it harder to afford other premium talent, but the team was still happy to have him.
And there it is: despite the fact that Greinke has essentially lived up to the outsized expectations of his contract, the Diamondbacks haven't won. And now they can no longer afford to try.
If the Phillies win the World Series before they inevitably have to trade Harper, then the deal is a winner. You can't put a price on a championship. The same applies for San Diego, though maybe even making a playoff appearance or two and being relevant would be enough return for the Padres before Machado gets shipped out. But the more likely scenarios, those that have played out with near regularity, don't come with a storybook ending.
