Going "all-in" might be largely subjective, but there are some reasonably objective standards that can be applied.  Although a general manager almost always could have done a little bit more, there is a clear continuum with regard to how aggressively a GM is building a team.  As a working definition, going all-in means assembling more talent for a given season or a set of years than a team would normally be able to do.        

Three main ways of going all-in occur to me: 1) the way a team structures, re-structures contracts or extends players; 2) the way a team handles their draft picks; 3) the way a team uses free agency.  Let us look at each in turn.

CONTRACTS:

Pushing cap hits into future years is the primary way to get more proven talent on the field for a given set of years.  For the last decade the Packers have structured their contracts so that the large cap hit numbers start to approach the AAV in year two and exceed it in years three and four.  The Packers usually just convert base salary and roster bonuses into signing bonuses on an as-needed basis.  If the team starts using option bonuses, void years, and guaranteeing money in the out years, that would be much more aggressive than anything the Packers have done to date.  Those things and just the sheer amount of cap space the Packers elect to generate will tell fans how all-in the team is for 2021 and beyond. 

A current example of going all-in is Pittsburgh.  The Steelers just re-structured Ben Rothlisberger's contract.  He had a $41.25 million cap number for 2021.  First, they persuaded him to take a $5 million dollar pay cut (from $19 million to $14 million).  Then they turned every possible nickel of his remaining cash into a signing bonus.  Because 2021 was the last scheduled year of his deal, the Steelers added four (count 'em, four!) void years.  Since the Steelers arguably did all that they could with Big Ben's new deal short of a steeper pay cut, the Steelers did not need to know the exact number for the 2021 salary cap, whereas it looks like the Packers are waiting to see how much cap space they need to generate before they make any additional moves. 

The restructure generates $15.34M in additional cap space in 2021 for Pittsburgh.  Here is what Rothlisberger's deal looks like now according to Overthecap.com (and it looks nothing like any contract the Packers ever reached):

Rothlisberger has a lot more mileage on him at age 39 than Rodgers has at age 37, including four more seasons as a starter.  Given Rodgers' statements that he wants to play into his forties, the Packers are looking at a set of years (known colloquially as a "window") but the exact number is unknown.  Rodgers' willingness to continue to play and his ability to defy the ravages of Father Time are uncertainties that affects the Packers' overall decision-making.

The Packers will soon make additional moves to get not jusr get under the salary cap but by enough to position themselves to retain some of their own UFAs, RFAs, and/or to sign outside free agents.  How much space they generate will be telling.

Another way to go all-in is simply to retain players that otherwise might not be kept.  Preston Smith and Dean Lowry have been discussed a lot.  The team could demand pay cuts, for example, or just bring them back.  While it is easy to assert that a day two or day three draft prospect would be better in 2021 than Lowry, one might bear in mind that third-rounder Montravius Adams was unable to supersede Lowry in four years, and fifth-rounder Kingsley Keke has been unable to supplant Lowry in two seasons.  Another way would be to extend players the Packers might not otherwise have taken that risk on.  Turner, for example, will be 32 when his current contract expires.   

Objective Criteria:  How much cap space will the Packers wring out of players currently under contract?  They need to generate $23 million MORE in cap savings at a bare minimum, which does not allow for signing their own UFAs, RFAs or any outside players.  Ken Ingalls suggests that the Packers need $24 million more here.  However the Packers go about it, here is my chart summarizing various levels of aggressiveness:

* Subject to any increase in the salary cap limit.  These numbers assume a $180M cap limit.

Under the medium level of aggressiveness, that would mean about $12 million to spend.  Tonyan ($3.3M), Sullivan and Lancaster ($2M?), Lewis ($2M?) seem like good bets, and that would leave a bit under $5 million.  The Packers might be able to sign Williams or King for that cap number, perhaps with some change left?  The other names probably each cost about $300K more than a UDFA or late draft pick (using the Rule of 51).  The team should probably generate $1 or $2 million more if needed to retain some of the RFAs and low end UFAs while mixing and matching the names they want to keep.  Tagging Jones might mean keeping just Tonyan and Jones.  How many of their own UFAs and RFAs the Packers retain is fairly subjective, but keeping more rather than fewer would seem indicative of trying to win in 2021.

DRAFT PICKS:

It is very difficult to tell whether a team drafted the best player available or if it drafted for need.  By need, I mean immediate need, as practically every position could become a need in the long term.  Drafting a player with a higher floor or who is more ready to play than a more talented player probably should qualify as going all-in, but it is largely pure opinion.  For example, I distinctly remember being relieved when the Packers drafted Bubba Franks with the 14th pick in 2000.  I was pretty sure he would block pretty well and catch a reasonable number of passes right away, while not thinking he would be the second coming of Tony Gonzalez (or later, a Gronkowski).  Some decisions like drafting Jordan Love and to a much lesser extent a player who would have to learn a new position like Rashan Gary are fairly obviously decisions with the longer term in mind.  Except at the extremes, who the team drafted is largely subjective in terms of going all-in.

Trading draft picks for veteran players is much easier to identify as going all-in, especially trading future draft picks for current NFL players or future picks for current draft picks, and to a lesser extent to move up in the draft (recall the Saints trading a future first to move up for Davenport).  Since the Packers in my opinion have a two to four-year window, it is still important to acquire young, low-cost, players with talent via the draft.  If one thinks the window is just 2021 and 2022, then the Packers should be more aggressive with their draft picks. 

Verdict:  So far, there have been no trades of picks for established players, either at the beginning of the season or just before the trade deadline, which suggests a less than aggressive mode.  The drafts have been a mixed bag in terms of aggressiveness.  In Gutekunst's first year, he happened to select more players who played positions at which the Packers needed immediate help than coincidence probably would suggest is likely (CB, CV, TE, and WR, WR, WR in rounds 4-6), and then moderated that tendency in 2019 and even more so in 2020.  I would not rate this aspect of the Gutekunst tenure as very "all-in" on the whole to date; he has probably been about average.  It remains to be seen what the Packers do in the 2021 draft.

FREE AGENCY:

In 2018, GM Gutekunst decided to buy four players he hoped would be starters or significant contributors in Graham, Tramon Williams, Marcedes Lewis and Muhammad Wilkerson plus another player he probably hoped would not be a starter in Byron Bell.  He also acquired street free agent Bashaud Breeland four weeks into the season and traded Pipkins for Antonio Morrison.  GM Gutekunst bought four more starters in free agency for 2019, which overall has paid off quite well.  In 2020, the Packers signed Funchess, and replaced Bulaga and Martinez with probable downgrades in Kirksey and Wagner.  UDFAs are usually depth players at best, but Gutekunst has been very active in terms of acquiring players.  

The team also has several restricted free agents who are players of varying ability but who probably are more ready to play in 2021 than the general run of the mill UDFA.  No doubt the Packers will retain Tonyan one way or another, although using anything less than a second round RFA tender or reaching a deal for a year or longer could get risky.  Their other RFAs like Lancaster, Sullivan, Greene, Redmond, and Boyle are probably more ready to play now than late round draft picks and UDFAs will likely be, so it will be interesting to see how many of these players the Packers keep and how much risk they accept in their attempts to retain them.  The Packers may elect not to tender most of them, letting them test the market or reaching a one or two-year deal with them.

Verdict:  The 2018 moves were rather moderate given the deficiencies in the roster.  Graham at $10 million was significant but not quite a blockbuster move.  Williams and Wilkerson were both mid-money and fairly low risk moves, while Lewis was for modest money and one year.  Bell was a bandaid.  The Packers certainly patched holes but without being truly aggressive.  It was McCarthy's last year, but I do not want to speculate about how his presence might have affected Gutekunst's decisions.  2019 was clearly an aggressive year and those four deals were all back loaded as to their cap hits.  The holes filled by those signings were glaring needs.  2020 simply replaced departing players with lower cost players, other than Funchess.  Still, due to 2019, I would rate signing outside free agents as above average in terms of aggressiveness and going all-in.  One indicator for 2021 is how many of the RFAs and low-end UFAs do the Packers retain.

CONCLUSION:

I do not believe that the Packers have been close to all-in since Gutekunst became general manager, nor do I think the Packers should have been extremely aggressive in prior years for two reasons.  The first is because the roster initially had too many holes to fill when Gutekunst became the general manager.  2018 and 2019 were about mini-reloads.  The other reason is because the team's window was long enough to allow the new GM to build the team using traditional means with a moderate amount of aggressiveness overall.  The Packers should get more aggressive as Rodgers ages since the window will close when he retires or becomes ineffective.  

At the latest, it should be time to go all-in when his crystal ball tells Mr. Gutekunst that Rodgers has two or at most three seasons left of being a top quarterback.  So far, either that has not yet happened or, despite back to back 13-3 seasons with losses one game shy of Super Bowl appearances, the Packers are not inclined to ever get seriously aggressive in their management style.