Shipbucket

Because it overflew uncontested airspace. The RA-5C Vigilante was about as fast of an aircraft as you can find in Western air forces this side of the SR-71 and its losses in Vietnam were relatively staggering.
I mean for the OP to think about his national air force realistically.

Hmmm no love for the F-14. If it had been allowed to evolve into a new production Tomcat 21 with full multi-role crews would still be wearing the "Anytime Baby" patch. That the Iranians have been able to keep a few flying US naval aviation should feel like its been wacked in the gonads by a wrecking ball.

Sorry but I'm not sure I follow? Route planning has always been of paramount importance for recce pilots, so naturally you'd avoid enemy AD threats if possible. Rafale and Gripens flew recce sorties over Libya and that wasn't exactly Soviet PVO resistance waiting for them. F-14s did it over Kuwait/Iraq, Afghanistan and Serbia and with the digital TARPS upgrade it could provide real-time intel.

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Republic of Lisenia AU - In progress
Republic of Lisenia in FD Scale - In progress

The Tomcat 21/Super Tomcat would've been, depending on the iteration and who you ask, the equivalent towards the Super Hornet in terms of how extensive a redesign it would've been. It would've been a very effective warplane - but they didn't build it.
I'm trying to illustrate that just because a plane is all awesome and tacticool and effective in a role it was not originally designed for in a low-risk environment doesn't mean it should be kept around forever.

I think I had a heart attack when I saw that someone actually voted for the F-14. Anyway, the F-14, especially in an upgraded form could amount to a great multi-role platform. Give it a new radar set and new engines/weapons and you could get plenty more life out of them. On a side note, just playing devils advocate here.

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Everyone is a genius. But if you judge a fish on its ability to climb a tree, it will live its whole life believing that it is stupid. - Albert Einstein
The only stupid questions are the ones that go unasked.
Korean AU

I think everyone would agree that the F-14 was a decent naval fighter, and I totally disagree with the statement that they were able to get only limited air-to-ground capability out of it. After the A-6 was retired they put targeting pods on the Tomcat and used it specifically for dropping precision guided munitions, mainly laser-guided bombs and later some JDAMs, and they never even tried to get any other ground-attack/close-air-support capabilities out of it because there were other airframes to fill those roles. Bottom line is the F-14 performed a role it was never intended for very well. In fact, it performed every role they used it for, whether it was air-to-air, air-to-ground, or photo-reconnaisance quite competently. That being said, the entire F-14 fleet was getting seriously over-used and was wearing out way too fast, and it was just not cost-effective to keep upgrading them and maintaining them. The main reason they were retired was cost-concerns and a shrinking navy budget. And of course, when the Super Hornets came on line there was simply no longer a justification for keeping them.

I love the Tomcat but isn't the design getting a bit old

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Projects:
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References and feedback is always welcome!

The F-14 is not the only air-superiority fighter that has proven it`s ability as a multi-role/fighter bomber. Other examples are the F-15 and F-16. Both are very capable bombers. Also the B-52 was never made to drop anything other than hydrogen bombs. Look at it now. Some planes are just so well built that they can do anything, the F-14 is a good example of that.

Yeah, the F-14 had pretty much reached the limit of usefulness they could get out of its design. If you were going to make a modern version of it you may as well just start over from scratch with a totally new design with only vague references to the F-14's design and capabilities.

Like TimothyC stated earlier, the most important criteria here is the time period. If we're talking 1970s-1980s, there really is nothing on the market that can match the F-14 as a fleet fighter. And unless you're an important US ally, there's no chance of getting them in the first place.

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Republic of Lisenia AU - In progress
Republic of Lisenia in FD Scale - In progress