Did Shad Khan make things too comfortable for Dave Caldwell?

This summer, the Jacksonville Jaguars were expected to be the darling team of the NFL — Blake Bortles the gunslinger, Gus Bradley the nice guy, Allen Robinson the prodigy, and a host of new defenders who were going to make insanely athletic plays while gelling into a unit that was fast, tough, and arrogant.

Everyone thought we were going to compete for the AFC South title and then — oh yes — make some noise in the postseason.

Everyone, including Sports Illustrated’s Greg Bishop.

Bishop pre-wrote a piece months ago and his editors shelved it after seeing how badly the team was performing. But then on Tuesday, they released it, sprinkling in 20-20 hindsight and self-deprecating jokes. It was fascinating insight into an alternate dimension of sorts. What would we have read had the Jaguars lived up to lofty expectations? I recommend you all go read it.

But before you do, there was something that caught my eye. I talked about it on this week’s Keep Choppin’ Wood episode. It’s this sense that in the beginning of this whole rebuild, new owner Shad Khan made things a little too easy for general manager Dave Caldwell.

In the middle of Bishop’s piece is an anecdote about how Khan and Caldwell matured in terms of their relationship and the challenges Caldwell most felt at the onset of his project.

Compared to those Buffalo squads, the roster Caldwell inherited in Jacksonville looked more like the old expansion Jags. Early on, his team struggled even to find a player with enough cachet to bother printing on season tickets. Caldwell told Khan he needed time. Khan tried to reassure Caldwell, pointing out the length of his marriage (now 35 years) and the nine executives who have each worked for him for more than 20 years.

I don’t know why Khan using his 35-year marriage to reassure his rookie general manager gives me pause, but it does. And the fact that this came at the beginning of the process, when the foundation was being laid for how this whole experiment would go.

Khan apparently got through to Caldwell, who molded this team into his own image.

Three seasons later, Caldwell reclines in the same leather office chair where he made many of his 750-plus personnel transactions, including 488 in his first two seasons alone. The Jags’ depth chart is laid out on the white board to his left. Five players from ’13 remain; the rest Caldwell picked or signed himself. His first three drafts yielded 21 players who have played in a combined 452 games, 304 of them starts.

This roster is Caldwell’s roster. He was given cap space galore, insane autonomy and agency from Khan (as compared to what we see other owners in the league doing), and going on five straight years of top-five draft picks.

And we have 14 wins in a little less than four full seasons.

Listen, I get that Khan had to encourage his new general manager. He was a rookie and he was tackling one of the biggest rebuilding jobs in recent memory. This was a complete tear down. But I don’t know if the degree to which Khan assured Caldwell is healthy. Caldwell is probably a very self-motivated person. But we all need external factors to push us to be better. If it’s all internal, there’s a ceiling.

What do you think?