Bo Racho

"Pujols"

"yacht fuel"

the inspiration for this thread:
"now he'll sign with Oakland and become an all-star"

this thread . . . 
 

not gonna lie, that sounds awesome. 

any team who gives Machado $350M is crazy. 

any team who gives Machado $350M is crazy. 

any team who gives Machado $350M is crazy. 

this is true although I disagree with your estimates of what Machado and Harper will get.   Agree that the total amount needs to be more than Stanton and the AAV more than Kersh.  
We all know that both Harper and Machado are better than Jason Heyward who got 8/$184.  
Heyward for age 20-25 - 29.8 bWAR .  
Harper for age 19-25 - 27.5 bWAR (with a few games left)
Machado for age 19-25 - 33.0 bWAR (with a few games left).  
Stanton for age 20-24 (ages prior to extension) - 21.3 bWAR - so one less season than Machado and two less than Harper.  Plus, his deal included buying out two years of arb that included age 25, 26 for 15.5 mil  So the deal is really 11/$310 starting from age 27.  
So let's consider a few things:
First and foremost.  I don't think teams are going to pay $30+ mil for those guys age 33-36 seasons.   I think the market has changed.  The Cano, Fielder and Pujols deals are certainly a factor in that thought process.  
An interesting consideration is advanced defensive metrics.  Machado is not a good SS and Harper is not a good OFer.  Poor defense ages poorly.  
Both have had some excellent seasons but also some head scratchers.  
Machado is likely more valuable but Harper had Boras.  However, Boras got his ass kicked last year.  
Who's gonna pay 300-400 mil for one player relative to their current situation?  
AL East. Boston - maybe, but I kinda doubt it relative to their current payroll, success without said player and what they're gonna have to pay a bunch of their young guys soon.  NY - same as boston but a little more likely for Machado cuz they're the yankees.   They could trade Andujar for a pitcher.    
No one in the AL central - CWS could be a dark horse for one of them.  that would actually drive up their price big time.  
No one in the AL west (the Angels have their $400 mil guy.  they aren't getting another that's close)
NL West - the dogs might but they're fairly savvy these days and they will likely extend Kersh.   The Giants can probably afford it but they have to know they're circling the drain and headed toward a rebuild.  
NL Central - Cubs and Cards are candidates.  Cubs are already staring at going well past the lux tax if they pick up all their options.  Cards actually make a lot of sense for either.  They've got very good young pitching, payroll space, and could use a young punch to the middle of their lineup.  Probably my top pick for where one ends up.  My guess is Harper because I don't think the Cards have a great relationship with Lozano anymore (Pujols and Machado).   They have no Lozano rep'd players right now.  
NL East - I could see the Nats retaining Harper.  I think Atlanta could be in play for either and of course Philly is in play as well.  
I think you have to ask yourself if any of those scenarios end up with one of those guys making $400 mil.  I think $300 will be the absolute max.  
That said, I think Trout will get an AAV of 37m.  I think he'll get a 9 year extension with an opt out after 3 yrs.  So 9/333.  
 

Lol.  Ya.  No big deal. 

any team who gives Machado $350M is crazy. 

Its not my money.
But seriously, that contract won't be enough, Griffey. He's going to be paid more--both per year and total contract--than any player ever. Right now the records are:
$35.5 million per year (Kershaw)
$325 million total (Stanton, 13 years)
To start, we have to speculate on what Machado and Harper will get. We won't know until they actually sign, but it will likely be as much or more than Stanton but in fewer years. Let's say that they both get somewhere between 10/$325M to 12/$400M. 
Trout will make more.
Trout is currently making $34.1M per year, through 2020, his age 28 season. I think an extension adds 8-12 years. Let's just say ten. 
So how to rework Trout's 2 years at $34M to 12 years?
The bare minimum will be 10@$35M per year = 10/$350M. But I think realistically you add two years and have to expect at least $40M per year average, so 12/$480M. Add in some bonuses and incentives we're looking at 12/$500M. That's my prediction, with a four-year opt out and probably weird clauses and stipulations that befit one of the greatest ever. Maybe he gets some deal that guarantees him $450M but can earn him $500-600M.
What would I pay him if I'm Arte? As much as it takes...within reason. But I might start thinking twice once we got over 12/$500M. But I'd guarantee that much.