There will be 500-page books written over this subject in the next year or two, but I would draw my own particular list up and just make five blunt assessments:
1. The number of fronts. You can make the case that four fronts existed (Belarus north, Russia north, far eastern area, and the coastal area).
In their mind....somehow 150,000 troops would be enough, and they were 'capable' of some massive assault on four fronts.
I think if you'd gone to Pentagon planners.....they would have eventually said you could have two front (near or adjacent to each other) with the 150k number, or you'd have to go with 300k for the bigger 'goal'.
This front episode also laid out a massive logistics mess, because they really weren't prepared for an incursion of this type....on four fronts, with the fuel, ammo, and supply convoy requirements.
2. Just an awful lot of unsecure communications.
It appears (based on news reports) that they were still using 1980s-type technology, and a lot of what was talked about via unit-to-unit communications....was picked up by the Ukrainians....so they knew positions and 'orders'.
On top of that....the use of cellphones was noticeable, and those were intercepted as well.
Where were the secure radios/comm devices? Unknown. Maybe this was another ordered item....that half the funding went to an Oligarch 'pocket'.
3. Some assessment of the Ukraine and west drove the planning process, and that failed miserably.
Whoever wrote the FSB (former KGB) assessment on how the Ukraine were react, and how the West might interpret the situation....had no idea about the landscape.
Course, if you went to most journalists in Europe or the US....they would have said that France and Germany would have just stood there....unable to react one way or another. This was a rare occasion where things evolved quickly, and sanctions went in a miserable way for Russia.
4. The value of fuel for tanks and armor.
One single US armored division will burn 600,000 gallons of diesel per day. No one in the Pentagon would support a front....where you don't have the fuel necessary to carry out a minimum of thirty days of fuel, and the means to deliver that fuel to the 'front'.
You have all kinds of cases where APCs or tanks branched out on a mission and reached a point four hours later....where the fuel tank was empty....the vehicle stopped, and they sat there waiting for fuel to be delivered. The Ukrainians were smart enough to realize the issue....attack fuel convoys, and then go after tanks which could not move forward or backward because of the fuel lacking.
A lot of the Ukrainian luck in taking out tanks....leading back to a fuel lacking issue? yeah.
5. Finally, there is the element of Putin not being competent on military strategy, and just seeing the big picture 'ending' (that he would rough up Ukraine, take two districts...perhaps all of the eastern half of the country, and that no outside group could affect the economy of Russia).
In simple terms....when plan 'A' failed, there should have been a plan 'B' in existence and things should have gone to that....with lesser goals. But no one can suggest a plan 'B' unless Putin himself comes up with the idea first.
In some ways, this is a repeat of the 1938 situation with Hitler and the German Army.
All Putin can do now? Well....he can blame people for the failures....fire them....throw 'bosses' into jail....and run the propaganda machine on turbo (for the time being).
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