LTG (retired) Mike Flynn has become a Trump advocate and appeared at the Republican National Convention. General (retired) John Allen surprised many by not just speaking at the Democratic National Convention but giving such enthusiastic support to Clinton. The big question is: is this problematic to have recently retired military officers take such public positions in the middle of a national election? Yes. But what can you do?
Let's talk about the yes. The former Chairman of the Joint Chiefs of Staff, General Martin Dempsey, is peeved (update: so much so that he wrote more here). Peter Feaver, who is perhaps the best published and certainly one of the sharpest minds on civil-military relations, does a nice job of laying out the case why it is bad. It degrades the military which becomes seen as a partisan actor in US politics. It raises questions for the President and for Congress whether generals/admirals near retirement (and all are near retirement in the up or out promotion system that is particularly intense at the highest levels) are offering their best military advice or are shaping their views based on their political preferences. The US is best served by an apolitical military. So, yes, great privileges are accompanied by great responsibility (almost the Ben Parker principle).
Moreover, these officers are not really adding much to the debate despite the risks to the military and to civil-military relations. Each campaign can find some officers, so it really does not demonstrate that one candidate is better for national security than the other. Sure, some campaigns will see a candidate with a longer list, but most Americans do not count how many officers are on one side or the other. It may matter if one surrogate sucks (that would be you, Flynn), but not much really. The good news about the state of US civil-military relations is that there are plenty of other experts, not dressed in uniforms in the recent past, who can speak about the national security implications of each candidate and their platforms. Campaigns can roll out former Secretaries of Defense (ok, maybe not Trump), think tank experts and defense pundits, and even former junior officers who don't have the same weight of responsibilities as the former senior officers.
But there is a basic problem as Feaver alludes to when he mentions arms race. The major parties face, dare I say it, a prisoners' dilemma. Each is best off if only their party gets a major ex-officer to speak for it, each is second best off if both parties refrain, a party is worse off if it refrains and the other party does not, and both parties face the second worst outcome if both get officers to speak as they don't get much benefit but have tarnished the military. And guess where we are? The usual equilibrium of prisoners' dilemma--both worse off.
Trump's campaign as first mover could have refrained, which would have put less pressure on the Clinton campaign to have a general speak. Once Flynn spoke at the RNC, the Clinton campaign could have unilaterally disarmed in this competition, it could have sent up a sharp, well-respected former Sec Def, or it could have done nothing. It chose to put a general in prime time, complete with a bunch of vets standing beside him (a bit much?), and had Leon Panetta speak (a former SecDef even if not a universally lauded one). I do think that doing nothing was not possible. I would have loved to see Robert Gates instead of Panetta, but that was probably not possible. So, I cannot condem the Clinton campaign although I, like others, can wish that neither general spoke out.
To be sure, this is not a big crisis in civil-military relations. The big one is if Trump becomes President as he has already promised to ask the military to do things that they find to be illegal, counter-productive to American interests, awful and/or all of the above. And Turkey also reminds us what a real crisis in civil-military relations. This "crisis" is very much a first world problem--the US military is not going to be a significant actor in the 2016 race, just as it played no role in the contested 2000 race, where the sides ran not to the military but to their lawyers and to court.
Anyhow, the basic points here are that expecting restraint by the campaigns is pretty unrealistic, and the number of retired senior officers is big enough that campaigns can always find someone who is willing to speak despite the preferences of the current and recent Chairmans.