There are many reasons:

1. Weakens civilian control
2. Creates bias due to closeness with officers & parochialism
3. Retired GOs usually lack of right policy & political skills
4. Heightens risks of politicization
5. Creates cultural expectation of mil in politics

[Thread] 1/15 https://twitter.com/mattyglesias/status/1336308529695760391
The National Security Act of 1947 EXPLICITLY created the Secretary of Defense as a CIVILIAN position to provide military oversight.

It also left the mil divided by services, with no officer in charge of all branches. The CJCS, the senior mil officer, has no command authority. 2/
This was intentional to keep any mil officer from gaining too much power or influence over military forces or govt policy.

With the resources & political influence as the military has, these create longer term risks to democracy, accountability, & civil liberties. 3/
Even before Mattis, there were signs that the military was becoming too influential in politics and over-powering the views of civilian policymakers. A military SecDef usually brings in military folks that make this challenge harder. 4/ https://www.usip.org/sites/default/files/2018-11/providing-for-the-common-defense.pdf
It is also the case that military officers typically don't have the necessary political skills for the job you would do as Secretary of Defense. As @ahfdc describes, these skills are primarily political -- not military. 6/ https://warroom.armywarcollege.edu/articles/what-makes-a-civilian/
In their own ways, Mattis, McMaster, Kelly and other retired officers have really struggled with the job. They tried to divorce politics from the job, but the job is really about politics -- choosing between competing priorities and managing relationships on the Hill, etc. 7/
It also risks politicization of the military. This can happen under a weak SecDef, like Esper, but it is more likely with a military officer. Mattis letting Trump sign the "Muslim ban" in the Hall of Heroes, for example. Again, this is tied to political skills. 8/
Many officers simply have been inculcated with can do values, and the non-partisan norm, and don't fully realize the political implications of their actions.

This can draw the military further into politics in unhealthy ways. 9/
It also has cultural impacts on society. It confuses people about the military's role in our government and society.

My own research with Peter Feaver shows most people in summer 2019 weren't even able to distinguish whether Mattis was retired or on active duty. 10/
It further creates the expectation that military should primarily be playing partisan roles. It blurs lines we draw in politics to try to maintain our democratic traditions by keeping the military from using force or political prestige to dominate our politics. 11/
And, in the current moment, it heightens partisan politics -- and creates the impression that these norms are okay if our side is doing it. That is risky not just because of polarization, but also because it creates incentives to "recruit" military folks as political allies. 12/
These dynamics can carry over onto active duty, creating strong incentives for military officers to behave as partisan actors instead of as a non-partisan policy tool. Of course, the military is always involved in politics, but we also need some real military expertise. 13/
Bringing partisan polarization into the senior ranks of the officer corps or the force -- there are already signs it is growing -- has damaging impacts on unity of purpose and military effectiveness. 14/
In short, there is just not a good reason to nominate a retired general or admiral when there are other civilian candidates who are better qualified for the actual job of Secretary of Defense.

And once we take these steps, it is hard to go back -- as we're already seeing. 15/15
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