In OTL, Toyotomi Hideyoshi sent Japanese Armies to invaded Joseon Korea, to conquer Ming China in hopes of honoring his late Lord Oda Nobunaga's dream, and to cement the Toyotomi Clan's security (Or to get rid of a bunch of samurai, by having them invade Korea). The Imjin War was a disaster, and ironically, further the collapse of the Toyotomi Clan.

Around the 1580s to 1590s, Toyotomi Hideyoshi feared Jesuit Missionaries coming into Japan and converting locals, to set up an invasions for Spanish Conquistadors. So, Toyotomi Hideyoshi started the first persecutions of Christians in Japan, by banning the Jesuit Missionaries and Christianity was repressed as a threat to national unity.

So, (and I know this sounds like a very outlandish idea), but what if, Toyotomi Hideyoshi, instead of invading Joseon Korea to conquer China, decided to deal with this Christian issue directly...by invading the Spanish Philippines.

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(Invasion Route- Map belongs to @Crazy Boris)

Hideyoshi gathers his forces, and sets up an large armada in Kyushu. Then these Japanese Forces goes and invades the Ryuku Kingdom, Island Hoping till they get to Formosa, and set up a small base there. Then they set sail for Luzon, landing in Pangasinan, and invades through different routes in the archipelago.

So with this idea set up, and the sailing to the Philippines goes smoothly, without any typhoons destroying this armada, how would this go for the Japanese?
How would the Spanish react to tens of thousands of Japanese Samurai and Ashigaru invading their territory?
How would the native Filipinos react to this?
How would the Ming Chinese react to this?
If the conquest was successful, would this set up future conquests in South East Asia?
If the conquest fails, would it still collapse the Toyotomi Clan earlier?
 
That’s a pretty far off location as far as logistics go. The terrain isn’t very good either. It kind of depends on how much military power Spain has in the islands at the time. Even if Japan manages to kick the Spanish out and not face problems with the natives, there’s always the chance the Spanish will come back with a proper fleet and marine forces to not only take back the islands but potentially shell some ports in Japan proper.
The Chinese wouldn’t be too bothered by this and if the Japanese aren’t any worse than the Spanish then their reaction shouldn’t be too different.
I can’t see too much if a reason for Japan to keep going unless they have some incentive to control the spice trade or to try and set up an alt-Singapore to control the trade to East Asia (which would likely draw China’s ire).
 
They lose a trade partner if they failed and turned a major power against them, they are importing Philippine gold in exchange for Japanese silver
 
One issue: What do the Philippines get you?
land that enterprising samurai can use, of which Japan has in excess supply

To be fair though, the Japanese may need to develop their naval technology to at least be more flexible in fighting off the Spaniards. If the Philippines turn into a war-torn clusterfuck with religious inclinations, then say hello to Balkans 2.0.
They would likely return the old ruling classes in power.
They may (and I like to fantasize about a native daimyo), but the Japanese needs to catch up on the whole blue-water navigation and logistics game to back up such political decisions.
 
They may (and I like to fantasize about a native daimyo), but the Japanese needs to catch up on the whole blue-water navigation and logistics game to back up such political decisions.
Might the Portuguese, Dutch, or, later on, English help in this regard if it means blunting Spanish influence in the region and perhaps a trade deal?
 
There is a lot of land in places much closer to Japan and where the Japanese would face much less resistance... such an operation would be a logistical nightmare and even if the invasion force reach their destination without resistance from the Spanish there is no chance to supply them from Japan, so they must fend by themselves and steal from the locals to live, if there is enough food to steal for everyone.
 
To be fair though, the Japanese may need to develop their naval technology to at least be more flexible in fighting off the Spaniards. If the Philippines turn into a war-torn clusterfuck with religious inclinations, then say hello to Balkans 2.0.

They may (and I like to fantasize about a native daimyo), but the Japanese needs to catch up on the whole blue-water navigation and logistics game to back up such political decisions.
The Japanese need a buffer with the Spanish and restoring the Kingdoms in Northern Luzon or creating a buffer state with the Spanish would be the best of their interest.
One of the reasons Japan decided to isolate is due to a lack of a buffer.
There is a lot of land in places much closer to Japan and where the Japanese would face much less resistance... such an operation would be a logistical nightmare and even if the invasion force reach their destination without resistance from the Spanish there is no chance to supply them from Japan, so they must fend by themselves and steal from the locals to live, if there is enough food to steal for everyone.
I agree with this.
 
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There is a lot of land in places much closer to Japan and where the Japanese would face much less resistance... such an operation would be a logistical nightmare and even if the invasion force reach their destination without resistance from the Spanish there is no chance to supply them from Japan, so they must fend by themselves and steal from the locals to live, if there is enough food to steal for everyone.
Agreeable; also, they may like labourers who would have worked on their lands. IOTL, this put Korea over Taiwan as the preferred place to conquer, especially considering that they also wanted to use the Peninsula as a springboard for the prospective invasion of China, which is a heck lot nearer to Beijing than Taiwan.
 
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Ming China may be totally indifferent to what the Japanese are doing on these maritime frontiers. However, if they are bothered by it, they are also still capable of intervening and causing serious problems for any Japanese conquest spree in this direction, as they, and their Korean allies, had better naval technology than the Japanese.

Prestige wise- China might be most offended by invasion of the Ryukyus, since that was formally a vassal Kingdom and tributary to China that OTL gave the Ming warnings about the Japanese attack in Imjin War (1592-98) and voiced support for China (I know ITTL this war is not happening, but it tells you something about the state of Ryukyu sympathies and contacts at the time).

Economically, it might be most inconvenienced by invasion of the Philippines, since this will at least temporarily disrupt Spanish galleons delivering New World silver and make south China merchants sad and reduce taxes, bribes, and kickbacks from the region. The next fleets the Spanish would try to send back would be naval and marine soldier fleets for reconquest as opposed to treasure fleets.

But this raises an interesting question. Supposing the Japanese get to the Philippines in force, and fortify it so that any Spanish reconquest attempts are repelled and Spain gives up?

Does Manila resume as the cross-Pacific trading route of silver for silks, just under Japanese management? Do Spanish and Chinese merchants still meet in Manila for trade, and just pay a a hefty tax for protection to the governing Japanese authorities?

Or, does the very act of conquest sever the trade route, a thus the main economic value, of the Manila/Luzon/Philippines area, leaving it just some more acreage for rice growing and sugar-growing if somebody decides to get creative?

Taiwan, ironically, without any developed kingdoms/states, or trade routes, would be the territory that Ming China and others would care least about Japanese operations in. As late as the 1680s, there were debates in the Chinese court about whether it was worth it for China to invest in controlling this "ball of mud in the ocean".
 
Does Manila resume as the cross-Pacific trading route of silver for silks, just under Japanese management? Do Spanish and Chinese merchants still meet in Manila for trade, and just pay a a hefty tax for protection to the governing Japanese authorities?

Or, does the very act of conquest sever the trade route, a thus the main economic value, of the Manila/Luzon/Philippines area, leaving it just some more acreage for rice growing and sugar-growing if somebody decides to get creative?
It depends on how willing the Spanish are to accept the loss if the trade value is still worth more than their pride. If it is then it’s a matter of how smart Hideyoshi and the daimyo in charge of the Philippines are in keeping the trade going with a tax that isn’t exorbitant.
 
It depends on how willing the Spanish are to accept the loss if the trade value is still worth more than their pride. If it is then it’s a matter of how smart Hideyoshi and the daimyo in charge of the Philippines are in keeping the trade going with a tax that isn’t exorbitant.

If the Spanish swallow their pride, and Hideyoshi finds a workable way to get his cut (with local daimyo getting a cut), that is not so exorbitant as to kill the traderoute or provoke a Ming or western challenge or rebellion the Shogunate cannot handle, could the Shogunate keep going nanban in the next generation?

Under a later Shogun, assuming the they stay up-gunned and get competitive in terms of armed warships, the next stop south could be the Molluccas, the Spice Islands. Could the Japanese seize them from the Portuguese instead of the Dutch doing it and charge western traders a fee?
 
Ming China may be totally indifferent to what the Japanese are doing on these maritime frontiers. However, if they are bothered by it, they are also still capable of intervening and causing serious problems for any Japanese conquest spree in this direction, as they, and their Korean allies, had better naval technology than the Japanese.

Prestige wise- China might be most offended by invasion of the Ryukyus, since that was formally a vassal Kingdom and tributary to China that OTL gave the Ming warnings about the Japanese attack in Imjin War (1592-98) and voiced support for China (I know ITTL this war is not happening, but it tells you something about the state of Ryukyu sympathies and contacts at the time).

Economically, it might be most inconvenienced by invasion of the Philippines, since this will at least temporarily disrupt Spanish galleons delivering New World silver and make south China merchants sad and reduce taxes, bribes, and kickbacks from the region. The next fleets the Spanish would try to send back would be naval and marine soldier fleets for reconquest as opposed to treasure fleets.

But this raises an interesting question. Supposing the Japanese get to the Philippines in force, and fortify it so that any Spanish reconquest attempts are repelled and Spain gives up?

Does Manila resume as the cross-Pacific trading route of silver for silks, just under Japanese management? Do Spanish and Chinese merchants still meet in Manila for trade, and just pay a a hefty tax for protection to the governing Japanese authorities?

Or, does the very act of conquest sever the trade route, a thus the main economic value, of the Manila/Luzon/Philippines area, leaving it just some more acreage for rice growing and sugar-growing if somebody decides to get creative?

Taiwan, ironically, without any developed kingdoms/states, or trade routes, would be the territory that Ming China and others would care least about Japanese operations in. As late as the 1680s, there were debates in the Chinese court about whether it was worth it for China to invest in controlling this "ball of mud in the ocean".
If the Spanish swallow their pride, and Hideyoshi finds a workable way to get his cut (with local daimyo getting a cut), that is not so exorbitant as to kill the traderoute or provoke a Ming or western challenge or rebellion the Shogunate cannot handle, could the Shogunate keep going nanban in the next generation?

Under a later Shogun, assuming the they stay up-gunned and get competitive in terms of armed warships, the next stop south could be the Molluccas, the Spice Islands. Could the Japanese seize them from the Portuguese instead of the Dutch doing it and charge western traders a fee?

The main enemy of Japan is not Spain, but the logistical issues, if they are able to win over the logistical issues only then they should consider the resistance from the Spanish and their allies. If by an enormous amount of luck and spanish incompetency and/or cowardice they are able to conquer not only Manila but the entirety of Luzon the Spanish will retreat to other holdings in the Philipines, if the Japanese go after these other holdings the Spanish retreat to territories further away or found new colonies from where they could trade with China without having to pay the Japanese.
 
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