So the guy had one good battle with perfect-set up and the advantage of reading the other guy's operations orders.
What did he do when set-up wasn't quite so perfect?
This is the guy got his ass kicked inbetween his ears time and time again trying to take Caen, and approved Market Garden.
Sure, if you're British, you have to like him because otherwise you're forced to conclude that the only competent general officers your nation produced between 1920 and 1950 were RAF. The rest of us, on the other hand?
I really think I should start my "Miles Dempsey for accountablilty" campaign. General Miles Dempsey throughout the Normandy Campaign commanded the British 2nd Army and as such was in control of all the tactical operations around Caen, Montgomery was 21st Army Group Commander and Ground Forces Commander until the Falaize Gap was almost closed and as such was in control of the whole campaign from the Canadian flank on the far left to the American flank on the far right.
In short, Montgomery was the boss, Dempsey and Bradley were his subordinates. It was Montgomery's job to decide how to procede with the campaign to ensure its victory - the strategic side - and to ensure that his armies got what supplies their needed - the logistical side - it was Bradley and Dempseys job to decide how to conduct the fighting in their areas so as to follow's Montgomery's strategy - the tactical side - as such overall resposibility for the successes and failures in both the British/Commonwealth and American sector of Operation Overlord is Montgomery's while the direct accountability for the successes and failure in those sectors are Dempsey's and Bradley's.
Overlord was Montgomery's victory.
Besides which the German forces concentrated around Caen were vastly superior in number and firepower to the German forces concentrated against Bradley - as was the plan - and Bradley's advance on Cherbourg was no better than Dempsey's advance on Caen, and Bradley eventual breakout toward St. Lo was no better handled by him than Goodwood was handled by Dempsey, the difference being there was no real depth to the German defences in Bradley's sector because they were all concentrated against Dempsey.
Bradley, a great Monty-Basher in his own right, praised Monty's plan for Normandy. As far as Bradley remembered the plan had always been to draw the Germans onto the British flank so as to ease the breakout for the Americans - he called it a sacrificial role for British pride - and in this the British were completely successful. Bradley further stated that people only thought of the action around Caen as a failure becuase they were judging it in terms of territory taken, not enemies drawn to it, held down and written off.
Eisenhower is somewhat to blame for both the split of the campaign between American and British sentiments and the prevailing idea that the action around Caen was a failure. He said after the war something along the lines of "once the British failed to break out the American's had to do it", this he said despite the fact that Montgomery and Bradley - two generals far more heavilly involved in the operation than Eisenhower - both agreed that no break out was ever going to be attempted in the British sector and that the mission around Caen was only one designed to hold down and write off the German reinforcement.
Montgomery did not approve Market Garden, that was Eisenhower. Montgomery first wanted to clear the Scheldt with 1st Allied Airbourne Army - two weeks before he submitted the Market Garden plan to Eisenhower he submitted a plan to clear the Scheldt - but Brereton and Browning refused to let their army be used in such a fashion and Eisenhower did not force them to clear the Scheldt nor did he put any importance on clearing it.
Montgomery then planned a limited coup-de-main simply to gain an approach to the Rhine but after some bad weather and increasing German resistance he canceled it. Then came Market Garden, an attempt to gain a Rhine crossing and outflank the Sigfried Line.
Eisenhower needed no coersion to support Market Garden. He had been under increasing pressure from Marshall to used the Allied Airbourne Army and Browning and Brereton wanted their army to be used as a forward tactical strike force so Market Garden was ideal for him. Once Montgomery submitted the plan Eisenhower jumped at the chance to let it go forward and insisted it be put into effect.
Despite all the mistakes made in the planning and execution of it Market Garden came within a stones throw of success - it was 90% successful but it had to be 100% successful for it to be useful to the Allies - and had Eisenhower supported it fully as he originally agreed to rather than let Bradley launch two full out offensives of his own (at opposite ends of his own line) at the same time - the Hurtgen Forrest offensive and the Battle for Metz/Lorraine Campaign) - it may very well have been a success.