While I understand this philosophy of "waiting for Mike Trout" and it does make some sense but, golly gee, the chances of ANY team EVER getting an opportunity to sign not one but two 26 year old mega stars in the SAME year are almost astronomically small.
Almost as small as a baseball team A] blowing a 6.5 game lead with 12 to play in '64, B] blowing a 2 run lead with two outs and no one on in the 9th inning of a playoff game and then calling it Black Friday or C] Playoff kingpin ace Cliff Lee blowing a 4 run lead at home in a 2011 playoff game. Impossible. Oh, wait...
Still, call me foolish but I find it ludicrous to deny yourself a chance to get both Harper and Machado simply on hypothetical grounds of perhaps chasing future free agents down the line. Look, Arenado has professed his hopes and desires to play for the Dodgers since he grew up in SoCal and still does. Boston is never going to let Betts get away, just not going to happen. As for Trout, sure it seems possible he could become a free agent in 2021 and want to come home to Philadelphia.
But I can also think of about 6 big salaried teams [Yankees, Dodgers, Cubs, Angels, Mets] that are not simply going to roll over and allow the best player in baseball to jet directly to Philadelphia without passing GO and making a huge effort to sign him themselves.
I know this much. Right now there is only one free agent reality and its that both Harper and Machado are 26, mega stars with their best years ahead of them and both are being courted by the Phillies, a team that can afford both of them. This will NEVER happen again. If they have a chance to sign both and fail to do so out of waiting for some future player who may never even taste free agency, I think it is a huge mistake.
This was to me that foolish idea that they absolutely couldn't have Cliff Lee and Roy Halladay on the same team at the same time because of potential money issues down the line. Lee was dealt within hours of Halladay being acquired and a good case can be made that this move didn't save them money, it cost them money. They had to bring in an expensive Roy Oswalt, re-sign a free agent Cliff Lee, then trade for an expensive Hunter Pence.
Keeping Lee and signing Werth when they could have would have saved them money...and made them money. Signing MM and Harper guarantees higher TV ratings, more advertising, sell outs in at least 50% of their games, potential playoff revenue and so much more.
I don't believe they will get both but I do believe they should try.