It's reasonable to assume, given what we know about the Phillies' pursuit of Manny Machado and their unwillingness to go to $300 million to get him, that their best offer to him was in the mid-$200 millions over a slightly shorter term.
Something in the $250 million range, perhaps higher, over seven or eight years — an enormous amount of money and also an average annual salary directly in line with what Machado will receive over 10 years from San Diego.
Such a deal would have netted Machado the highest per-year figure of any position player ever. In the end, he opted for the most guaranteed money and you can't blame him for doing so.
According to The Athletic's Ken Rosenthal, the White Sox offered Machado eight years and $250 million with options and incentives that could have taken the deal to $350 million. Those options, per USA Today, were two vesting options worth $35 million apiece.
You can see why Machado opted for the guaranteed money over the possibility of earning more through options and incentives. Those options would have obviously been at the very end of his deal, and it wouldn't have been overly likely that he'd reach them by playing or producing enough at ages 33 and 34. In other words, the $60 million guaranteed Machado will earn in Years 9 and 10 of his Padres deal will probably be more than he could've gotten after eight guaranteed years from another club.
You can't fault a team like the Phillies or White Sox for not matching 10 years and $300 million. "What's the difference between $250M and $300M," some might ask, but it's a huge difference. Especially when the $50 million difference in question would be paid during the player's age-35 and age-36 seasons, which don't figure to be great years. Players do not age gracefully in their mid-30s the way they did during the Steroid Era. It's a major reason why the multi-year deal has disappeared for veteran, non-star free agents.
Beware the mystery team
A few more interesting tidbits about the Machado negotiation process, from Joel Sherman of the New York Post.
Lozano/Machado asked teams for best offers in last week of 2018, idea was to eliminate 2 of 6 suitors and ultimately decide early in new yr. but to get to magic $300M had to keep grinding until 3d week of Feb. persistence literally paid off.— Joel Sherman (@Joelsherman1) February 19, 2019
The Padres did not emerge as an actual suitor for Machado until mid-January. It's yet another cautionary tale of why the connections made publicly aren't always the most meaningful. Everything about Machado-the-Padre now feels and sounds right, yet at the beginning of the offseason not a single person predicted it.
It's why you should be hesitant to instantly dismiss the words "mystery team" as an agent's construct. A lot of times, teams linger in the periphery and will be willing to pounce if everything lines up.
When will Harper sign?
By all accounts, Bryce Harper and Scott Boras are seeking a long-term deal, a similar length to what Machado received. But if the $300 million-plus offers for Harper do not materialize because fewer teams are in on him, Harper and Boras could change course and go shorter, which would bring more teams back into the fold. The complexity of this all is why a Harper signing might not be imminent. (Sorry.)
This process could end 20 minutes from now with a phone call, but there's also reason to believe it will plod along. Boras will find a way to extract top dollar even in an altered market. He almost always does.