The problem with your post is that you are ignoring two of the more successful baseball teams currently. The Dodgers and Astros have manage to be successful while keeping big money contracts to a minimum. Last I checked, the Dodgers signed Betts and the Astros extended Altuve. The next biggest contract for the Dodgers is Freddie Freeman and in terms of length and amount that has more in common with Story then Betts or Altuve or Machado etc. That is the plan currently. Get a core of young homegrown players and try to sign them to reasonable contracts when they are pre arb. Supplement them by signing the mid tier guys like Freeman. Also supplment them by using surplus farm talent to acquire players who under control for a few more years. Hand out massive contracts very rarely. While this method is not fool proof, it is more likely to be sustainable then the method employed by the Padres, Phillies, Mets and possibly Yankees.How about the Astros with Altuve? The Sox with Manny? The Giants in 2010, 2012, 2014 (Cain and Zito each for two of the years)? The market moves so 8 and $20 isnt particularly relevant - its more of a how many teams are winning without elite talent outside the 6 year control window? Because if you arent: (i) willing to take risk and extend guys early; or (ii) pay market rate, youre basically banking on the player loving it so much that they're willing to take a ton less to stay or that you can develop enough good talent close enough together. Neither of those places are good places to be. Dustin Pedroia types are not common and banking on the elite talent you develop also being like him is insane; you're doing well enough to develop elite talent - that in and of itself is hard.
It doesn't necessarily need to be free agent market rates - you can extend early. Historically teams have had at least one and sometimes multiple long market rate deal or even longer deal that was signed pre-arb. What is really hard is to just hope that you can line up pre-arb and arbitration guys closely enough to win - it does happen once a decade (Royals in 2015 and Marlins in 2003) or so by teams that cant afford to spend. Here's the evidence:
Basically, you can use whatever strategy you like that results in locking up elite talent long term, but just letting it go away is not a winning strategy. Most of the above teams had at least one market rate and/or long term star deal; some had two. Trying to build a team where you're overlapping really good to elite talent all within the six year control window is incredibly difficult. Its why the Rays haven't won and only one team a decade or so does it. Beyond the talent point, I think it provides a level of certainty for baseball ops to build around something that is already settled. The argument you're making just doesnt really hold water - almost all World Series teams have a long term/big money guy who materially contributes to the team.
- 2022 - Astros - Altuve
- 2021 - Braves - Pick whoever you want; Freeman was on the 8th year of an arbitration extension .
- 2020 - Dodgers - Kershaw; Mookie was signed long term but was still in his last arbitration year
- 2019 - Nationals - Corbin, Strasburg
- 2018 - Red Sox - Price
- 2017 - Astros - Justin Verlander (to be fair traded for him midseason, but they arent winning without him). Signed Altuve to a market deal in offseason before 2018.
- 2016 - Cubs - Lester
- 2015 - Royals - None
- 2014 - Giants - Matt Cain
- 2013 - Red Sox - Dustin Pedroia (I agree he signed at a significant discount, but he was no longer in the six year control; if youre lucky enough to get someone like this, great!), arguably Lester as well
- 2012 - Giants - Matt Cain, Barry Zito
- 2011 - Cardinals - Matt Holliday
- 2010 - Giants - Barry Zito
- 2009 - NYY - ARod, Jeter, CC Sabathia, Teixiera
- 2008 - Phillies - Chase Utley
- 2007 - Red Sox - Manny
The point isn't to say to blow huge money everywhere, but to show that the likelihood of being able to win if you dont have any elite talent outside of the 6 year control window is exceedingly difficult and willingly going down the path of trying to time overlapping control windows of great talent when you have the resources to choose a different path is bizarre.
The Sox have shown minimal interest in any sort of long term deal whether its in arbitration or free agency. This is how the market is moving so if they dont change their practices and beliefs its hard to see how they acquire and, to the extent they develop, retain elite talent.