AHC: Make Cuba An American State

I'd take pre-1900, actually.


In that case, here's an old soc.history.what-if post of mine:

***

My POD is the "Black Warrior affair" leading to war with Spain in 1854.
http://www.infoplease.com/ce6/history/A0807810.html It might have done
so--there were calls for the suspension of the neutrality act, which would
mean unleashing filibusters on Cuba--except that the Kansas-Nebraska Act
was pending in Congress, and anti-Nebraska forces raised a violent outcry
that the administration was looking for war as a way out of its sectional
troubles.

The turning point was probably May 30, 1854. On that day, Senators Mason,
Douglas, and Slidell--in short, the Democratic majority on the foreign
relations committee--met with President Pierce and urged him to support
legislation calling for a suspension of the neutrality act. Instead of
doing so, Pierce proposed to his callers "the creation of a three-man
commission to go to Madrid to present to the government in all seriousness
the desire for Cuba and to warn that probably only cession would stop the
filibusters. The three visitors accepted this plan, though far from
eagerly. As a part of the arrangement, [Secretary of State William] Marcy
was called upon to telegraph to the district attorney in New Orleans that
decisive measures were on the way. This was to help him hold the
filibusters in line. Pierce also promised that before the session ended he
would explicitly ask for a big appropriation, big enough for war purposes,
in case the commission was unsuccessful. On May 31, i.e., the next day,
Pierce issued a proclamation calling for an observance of the neutrality
laws." Ivor Debenham Spencer, *The Victor and the Spoils: A Life of
William L. Marcy* (Providence, RI: Brown University Press 1959), p. 323.

The result of Pierce's decision was to kill off the filibuster movement.
Its leaders, including Mississippi's ex-governor John Quitman, were even
required to give bond for their good conduct. Another result was a more
conciliatory attitude toward the Black Warrior incident. By midsummer, as
it turned out, Pierce had not dared to send Congress the proposal for the
commission, though that body was still in session; and the Senate foreign
relations committee decided not to ask for an emergency appropriation,
though Pierce had indicated his willingness to do so.

This does not by any means indicate that Pierce had given up on Cuba.
Something like the originally-planned commission was eventually created
and issued the famous "Ostend Manifesto"
http://xroads.virginia.edu/~HYPER/HNS/Ostend/ostend.html but by that time
the Democrats had suffered drastic defeats in elections in the North--due
largely to a backlash against the Kansas-Nebraska Act--and even Pierce
(let alone the more conservative Marcy) had to repudiate the Manifesto.

So basically my POD for US acquisition of Cuba is *no Kansas-Nebraska
Act*. Without this, Pierce and the overwhelmingly Democratic Congress
would probably have approved a quick suspension of the neutrality act
after the Black Warrior affair. And as I stated in a post a few years
ago, organization of Nebraska without repeal of the Missouri Compromise
was by no means inconceivable. For a while, even David Rice Atchison,
despairing of getting repeal through Congress, was willing to accept this,
but when other southerners showed an unwillingness to organize the
territory on this basis (giving, among other reasons, their well-known
respect for Indian land titles :) ) and when his bitter enemy Thomas Hart
Benton started to mock him for his retreat, he swore that he would see the
territory "sink in Hell" before giving it to the free-soilers. If just a
few Upper South senators had gone along with Atchison's temporary retreat,
there would have been no Kansas-Nebraska Act as we know it. There might
still be a controversy over slavery in Kansas--the Missourians there might
still try to establish it, arguing the Missouri Compromise was
unconstitutional, and a Dred Scott-like test case would make its way to
the Supreme Court--but at least the political explosion of 1854 would be
delayed. (Of course another way to have the Kansas-Nebraska bill as we
know it not come up is to have the Black Warrior affair happen a few
months before it did in OTL--in short, have the US get to the brink of war
with Spain *before* the Kansas-Nebraska bill is introduced. The war scare
would doubtless delay any decision about what to do about Nebraska.)
Secretary of State Marcy, never a great enthusiast for Cuba (and
especially opposed to taking it by force) pretty much summed up the
situation in a letter to Senator Mason on July 23, 1854:

"To tell you an unwelcome truth, the Nebraska question has sadly shattered
our party in all the free states and deprived it of that strength which
was needed and could have been much more profitably used for the
acquisition of Cuba." Quoted in Spencer, *The Victor and the Spoils*, p.
324

The South in 1854 was strong enough to get Cuba--or to get the Missouri
Compromise repealed in a futile effort to make Kansas a slave state. She
was not strong enough to get both, and disastrously chose the Kansas
shadow over the Cuban substance. (Of course the real disaster of Kansas
for the South was that it led to the rise of the Republican Party. I
doubt very much that a war with Spain, provoked by the Black Warrior
incident, would be enough to do so, even if it led to the acquisition of
Cuba as a slave state. Unlike Kansas, Cuba already had slavery, so
slavery would not be extended by its acquisition; it was even argued that
acquisition of Cuba would help stem the illegal African slave trade to
that island. And in any event, unlike Kansas, Cuba was not a place where
northern farmers were planning to settle.)
 

Delta Force

Banned
What about just the Island of Pines/Isla de la Juventud. Quoting from Wikipedia:

Following its defeat in the Spanish–American War and the Cuban War of Independence, Spain dropped all claims to Cuba under the terms of the 1898 Treaty of Paris. The Platt Amendment of 1901, which defined Cuba's boundaries for the purposes of U.S. authorities, left the ownership of Isla de la Juventud undetermined. This led to competing claims to the island by the United States and Cuba.[4] In 1907, the U.S. Supreme Court decided, in Pearcy v. Stranahan, that control of the island was a political decision, not a judicial one.[5] In 1916, a pamphlet titled "Isle of Pines: American or What?" called for the U.S. to annex or purchase the island to settle the issue.[6]

In 1904, Cuba and the United States negotiated and signed the Hay-Quesada Treaty, which recognized Cuba's ownership of the island. The U.S. Senate ratified this agreement on March 13, 1925, over the objections of some four hundred United States citizens and companies, who owned or controlled about 95% of the island's land.[7][8]
 
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