AHC/WI: Dakota Senator Roosevelt?

Your challenge, should you accept this offer, is to find a way to make the dude from New York the Senator of North, South, or a united Dakota. This challenge was inspired by the Rise of Theodore Roosevelt, where it was mentioned newspapers speculated he would be their first Senator.
 
It's morbid, but I suppose the easiest way to do it is to have his daughter Alice Roosevelt also die on the same day as his wife and mother. Without a child to inspire him to return to New York, maybe he just stays out in the Dakotas. There is his childhood sweetheart Edith Carrow, who later became his wife, that may have also encouraged him back to New York, but she could be the one to inspire him to run for the Senate while they rekindle their relationship from afar.
 
He has to avoid the financial ruin he met IOTL - either he avoids the cattle boom (land speculation? mining?) or he sells his heads before the winter blizzards that killed his herd.
 

Driftless

Donor
A POD might be having his cattle herd survive the winter of 1886-1887. Then, he might have stuck around for Statehood in 1889. His genuine sense of civic responsibility, plus a chance at some glory; and maybe he runs for Senator.
 
I wonder what Roosevelt's relations with the McKenzie machine would be, since it dominated ND politics up until the Progressive era in OTL.
 
It's morbid, but I suppose the easiest way to do it is to have his daughter Alice Roosevelt also die on the same day as his wife and mother. Without a child to inspire him to return to New York, maybe he just stays out in the Dakotas. There is his childhood sweetheart Edith Carrow, who later became his wife, that may have also encouraged him back to New York, but she could be the one to inspire him to run for the Senate while they rekindle their relationship from afar.

That might just break the poor man entirely.

He has to avoid the financial ruin he met IOTL - either he avoids the cattle boom (land speculation? mining?) or he sells his heads before the winter blizzards that killed his herd.

A POD might be having his cattle herd survive the winter of 1886-1887. Then, he might have stuck around for Statehood in 1889. His genuine sense of civic responsibility, plus a chance at some glory; and maybe he runs for Senator.

The Rise of Theodore Roosevelt gave me the impression that for all his intellect and people skills, the man was just not good at money making or quiting until there was no choice. So maybe on that idea. And reminder, Senators back then were chosen via state legislature, which leads me to...

I wonder what Roosevelt's relations with the McKenzie machine would be, since it dominated ND politics up until the Progressive era in OTL.

Roosevelt's likely opposition to the man. If I know anything about Theodore Roosevelt, it's that he wouldn't take a man like Alexander McKenzie lying down if he got in Roosevelt's way. We might see early state reform in North Dakota, similar to what the Populists would do around that time. Imagine that, Populist Theodore Roosevelt against a state Republican party. Unlikely, but fun to imagine.
 

Driftless

Donor
I wonder what Roosevelt's relations with the McKenzie machine would be, since it dominated ND politics up until the Progressive era in OTL.

Roosevelt's likely opposition to the man. If I know anything about Theodore Roosevelt, it's that he wouldn't take a man like Alexander McKenzie lying down if he got in Roosevelt's way. We might see early state reform in North Dakota, similar to what the Populists would do around that time. Imagine that, Populist Theodore Roosevelt against a state Republican party. Unlikely, but fun to imagine.

That woulda/coulda been epic... The "four-eyed" eastern dude up against the local machine. It sounds the story nugget for 25% of all of the westerns ever made; except this would have been for real. Both MacKensie and Roosevelt understood the higher levers of power, and used them. If that would have worked out to the Hollywood ending, that might have guaranteed Teddy the White House, with or without the Rough Riders experience.
 
That woulda/coulda been epic... The "four-eyed" eastern dude up against the local machine. It sounds the story nugget for 25% of all of the westerns ever made; except this would have been for real. Both MacKensie and Roosevelt understood the higher levers of power, and used them. If that would have worked out to the Hollywood ending, that might have guaranteed Teddy the White House, with or without the Rough Riders experience.

Well, I only have two caveats. The first being that TR was completely willing to use the boss in New York, until such a time as he was in the governor's mansion and could move against him. It is likely that Roosevelt would use a sinilar tactic against Mackenzie if he could; not make any overt moves until he was secure and then work against him.

Secondly, although a Senator of the era had a good deal of patronage power, Roosevelt was never a LaFollette; i.e. he never seemed to have the same Passion, or ability to use patronage and politics to build up a counter-weight to the bosses' machines. He was always much more comfortable going to the people and putting pressure on the elected officials that way. As a Senator, he would likely have less opportunities to do this than if he were a governor.

Now, although I doubt we would ever see Roosevelt as a Populist (that man was a loyal Republican, especially during thia point in his life), he would likely emerge as one of the great reforming voices in the state and would be one of the first Progressive leaders in the region. As such, it would be interesting, but I could see him and Bob LaFollette being natual allies (and, yes, the irony of those two getting along ...). On the state side, I could see him becoming close to other young reformers such as Usher Burdick. Actually, a Rooaevelt-Burdick friendship would be awesome! (Burdick was a fascinating customer in his own right, and pretty damned rough and tumble when he had to be)

Interesting enough, I wonder if a Senator Roosevelt would be aligned or opposed to the Nonpartisan League when it emerged (if it did). My gut says that, even if he was sympathetic to the NPL, he would be turned off by the leadership and the covert (sometimes overt) Socialist leanings of said leaders. And, of course, this leads me to wonder how TR would view good ol Wild Bill Langer (the only sitting governor to try to declare his state its own country after the Civil War :p. Ah, Wild Bill. Definitely the Starscream of the NPL!)
 
I hope Senator Roosevelt comes dressed to the capital as befits a Dakota man! :D

KFlHThj.jpg
 

Driftless

Donor
I hope Senator Roosevelt comes dressed to the capital as befits a Dakota man! :D

KFlHThj.jpg

Was this the buckskin suit tailored for Teddy by Brooks Brothers? He had at least one of those made during his cowboy days. It is kind of a metaphor for his cowboy period - he did the work and was shaped by his experience in the Dakotas, but he always had some hook back to the east.
 
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