The answer came in his third year in charge of the Packers' roster, and really it was a question that hung over his head from the moment he took over for one of his mentors, Ted Thompson, in January 2018.
It was just two months after that when Gutekunst was asked if he realized his legacy will ultimately hinge on whether he can find the next franchise quarterback without interruption.
"I don't think I'm thinking out that far right now," he said at the time. "But yeah, I know what you're saying."
Here's a look at some of the questions facing the Packers, Rodgers and Love as their arranged marriage begins:
How will Rodgers react?
Of course, we won't know until we hear from him, and even then his tone and cadence may tell us more than his words. Almost immediately after the pick late Thursday night, one source who has known him since he came into the NFL agreed that Rodgers initially would be irate that Gutekunst didn't get him any immediate help. The 36-year-old said after the NFC title game loss that he believes the Packers' Super Bowl window is open, and "I think we're going to be on the right side of one of these real soon."
But on Friday that same source, who stressed that he had not spoken with Rodgers since the pick, said: "I think Aaron will help the kid." Shortly after the Packers drafted Rodgers in 2005, Brett Favre said: "My contract doesn't say I have to get Aaron Rodgers ready to play. Now hopefully he watches me and gets something from that." The relationship was frosty at best that first season but improved over Favre's final two seasons with the Packers.
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Why could it work?
If Rodgers takes to Love and isn't driven into a state of bitterness by his presence, it could work out for the Packers. Favre had one of his best non-MVP years in 2007 after a terrible 2005 and a mediocre 2006. Rodgers didn't blow anyone away with his 2019 season, although he and the Packers found a variety of ways to win all the way to the NFC title game.
"There's nothing wrong with lighting a little fire under his [expletive]," one NFL source said. Rodgers has often used perceived slights to his advantage, from going under-recruited out of high school and starting out at Butte College to his slide to the Packers at No. 24 in the 2005 draft. While Rodgers has said he plans to play until at least age 40 and is under contract through 2023, they'd surely take two or three MVP-level seasons from him before deciding when to officially turn the team over to Love.
What's the financial implication?
Love's rookie contract should be in the neighborhood of $12.3 million (including a $6.5 million signing bonus) over four years, according to projections by Spotrac. By drafting him in the first round, the Packers get a fifth-year option. The $134 million extension Rodgers signed in 2018 makes him virtually untradable or impossible to cut until after the 2021 season. He has a cap number of $36.3 million in 2021 and $39.9 million in 2022. After the 2021 season, the Packers would save $22.648 million in salary-cap space but would have to count $17.204 million in dead money. If they moved on after this season, they would save only $4.76 million on the cap and have $31.556 million in dead money.
Why could it be good for Love?
If he can handle sitting -- and he said Thursday night that he's "going to take that time to be able to learn and grow as a player" -- then it could extend Love's career on the back end. He would save the wear and tear on his body early much like Rodgers did. He not only has the chance to learn from Rodgers but should benefit from a quarterback-driven head coach in LaFleur, much like what Rodgers had with Mike McCarthy. One NFL offensive assistant coach who evaluated Love said: "He's a gunslinging [expletive] who has interception problems, but he can throw it all over the place. He just needs a little time and needs to be coached. Let's see if [LaFleur] can coach now."
What does this say about Gutekunst?
He's not afraid to make a bold move if he thinks it's in the best interest of the franchise. If he's right about Love, it sets up the Packers for another decade-plus of success. Yes, a receiver like LSU's Justin Jefferson (who would have required an even higher trade up because he went No. 22 to Minnesota) would have helped in the immediate, but there should be capable receivers available on Day 2. In the deepest receiver class in years, the value will be there. Perhaps Gutekunst can win back Rodgers -- if he needs to -- by not only taking one in the second round but by trading up to do so.
Could Love actually help immediately?
LaFleur began to show his scheme creativity as his first season progressed last year. With a dynamic athlete like Love (4.74 40, 35.5 vertical), perhaps there are some Taysom Hill-like packages he could develop for his new quarterback. Taking Rodgers off the field is never a good idea, but if there's something that would create a matchup problem then why not explore it?