FDR in Cuba

[QuoProQuid]

Franklin Delano Roosevelt was a very unhappy teenager. Resentful that he struggled in sports and homesick at prep school, Roosevelt turned inward. His only social saving grace turned out to be his relationship with his cousin, Teddy Roosevelt. A small clique gathered around FDR, with hopes they would get to meet his famous relative.

In 1898 Roosevelt's friends were getting restless and the United States went to war with Spain. Thinking quickly the fifteen year old told his friends that he planned to run away from Groton Prep School, travel to Florida and then stow-away on a boat heading to Cuba. There, he said, FDR and his friends would unite with Teddy.

On the day they were meant to depart, Roosevelt became "sick" and had to cancel the would-be expedition. Assume that Roosevelt decides to play the scheme to the hilt and actually manages to stow-away on a boat to Cuba. What happens when he arrives and what is his family's reaction likely to be?

 

[Fearless Leader]

Such an experience could potentially completely alter FDR's life...Imagine if he manages to time his voyage correctly and show up prior to the Battle of San Juan Hill? I could see Teddy taking his cousin and his entourage under his wing as some kind of informal aide de camp. Might this lead young FDR to see action during the Spanish American War?

Perhaps FDR decides to pursue formal military service and attends West Point?

Certainly a small series of events stands to completely change his life trajectory.

 

[Japhy]

Considering the nature of the Transport to Cuba this idea makes exactly as much sense as it did when legions of 15 year olds thought about doing the same thing to sneak to France or Korea in the 20th Century.

No one was going to sneak onto a transport when they didn't even have room for the entire army they had to get to Cuba or be supplied there.

 

[Alamo]

No one was going to sneak onto a transport when they didn't even have room for the entire army they had to get to Cuba or be supplied there.

On the other hand, the American effort to invade Cuba was a complete circus in terms of transportation and organization. In the utter chaos, I could easily see Roosevelt getting lucky and slipping aboard a ship.

 

[Darth_Kiryan]

what about his polio

 

[Dathi THorfinnsson]

what about his polio

Otl, not contracted until 1921, so totally butterflied away.

 

[NothingNow]

On the other hand, the American effort to invade Cuba was a complete circus in terms of transportation and organization. In the utter chaos, I could easily see Roosevelt getting lucky and slipping aboard a ship.

Oh yeah. The hard part is probably just making it to Tampa. After that, the chaos is pretty much the perfect cover.

 

[Japhy]

Oh yeah. The hard part is probably just making it to Tampa. After that, the chaos is pretty much the perfect cover.

Not really. The chaos is chaotic for getting the right military units on the right boats. Not "an orgy of crazy where a bunch of teenagers could sneak onto a packed transport, make it to Cuba and not be immediately arrested when they are inevitably discovered".

 

[NothingNow]

Not really. The chaos is chaotic for getting the right military units on the right boats. Not "an orgy of crazy where a bunch of teenagers could sneak onto a packed transport, make it to Cuba and not be immediately arrested when they are inevitably discovered".

True, but if they were even half way serious about this, they'd at least have uniforms or typical seaman's clothing for the last mile.

...But that's also a great way to get shot as saboteurs.

Then again, the whole idea is pretty suicidal to begin with, considering that most likely none of the idiots involved were halfway prepared for the Cuban climate.

getting into Annapolis would've been a better way to meet Teddy really.

 

[RousseauX]

True, but if they were even half way serious about this, they'd at least have uniforms or typical seaman's clothing for the last mile.

...But that's also a great way to get shot as saboteurs.

Then again, the whole idea is pretty suicidal to begin with, considering that most likely none of the idiots involved were halfway prepared for the Cuban climate.

getting into Annapolis would've been a better way to meet Teddy really.

I don't think getting shot as saboteurs is particularly likely, the Rooservelts are an old, patrician, and very WASP (despite not being AS) family. I think if he got caught he wouldn't exact be recognized as a Spanish speaker whom you would expect to be saboteurs in the war.

But yeah, the plan is pretty suicidal. What if they actually get there and just contract yellow fever or Malaria?

 

[Cuāuhtemōc]

Chances are that even if everything goes right and FDR ends up meeting his famous cousin in Cuba, he'll probably be killed in battle or die of diseases.