I may be in a small minority, but I'd actually be fine with going into the 2022 season with this roster, if I was 100% sure we will be making a big move to get to a top 3-5 roster, next winter. I might even be fine for 2024, if we did enough to stay entertaining for these two year.
I'm having doubts about us going large and long enough to bring us another ring in the next 4-5 years. Maybe the plan is to try and get one without doing so, but will that mean we watch Devers and Bogey walk (or trade them?) I shutter to think of those upcoming rosters.
If the plan is to spend near the tax line every year, I think we are bound to be top competitors and some point in the next 3-4 years, but it remains to be seen, if we do it without some major "large & long" signings.
Here is a list of our last major signings:
Red= extension only from 2009 to today
2020
Sale $145M/5 w opt out
Bogey $120M/6 w opt out
2019
Nate $68M/4
2018
JD $110M/5
2016
Price $217M/7
Porcello $83M/4
2015
Pablito $95M/5
HRam $88M/4
2014
Pedroia $110M/8
2011
Crawford $142M/7
2010
Lackey $83M/5
2007
JD Drew $70M/5
2001
Manny $160M/8
Tier 2 (some not large-some not long & Kike and others not really large or long)
2022
$19M/2 Barnes
2021
Kike $14M/2
2015
$18M/2 Uehara
$19M/3 Miley
2014
Napoli $32M/2
R Castillo $73M/7 (IFA)
2013
Vic $39M/3
Dempster $27M/2 (retired after 1 season)
Ortiz $26M/2
2012
AGon $154M/7
Buchholz $30M/4
2011
Josh Beckett $68M/4
2010
Cameron $16M/2
2009
Youkilis $41M/4
Lester $30M/5
2008
Lowell $38M/3
2007
Dice-K $52M/6 (+ hefty posting fee as IFA)
Lugo $36M/4
2005
Renteria $40M/4 (ended u being about $40M/1)
VTek $40M/4
Clement $26M/3
2004
Foulke $26M/4
2002
Damon $31M/4
1999
Offerman $26M/4
Not counting trading for large salaries with multiple years remaining, like JBJ, Kimbrel, Allen Craig, Jake Peavy, VMart, Mike Lowell, Jason Bay