Theodore Roosevelt, the 26th President of The United States, still stands like a titan of history. His career, from a boxer and cow puncher all the way to the highest office of the executive branch reads like the bastard child of a documentary and an action movie conceived while fighting off bears in the depths of the forest. Roosevelt was a soldier, a fighter, a stone-cold badass, and a love of animals in all their various states. If you'd like to bring the rough-rider himself to your game, this guide should get you started.
If you're interested in character builds for other badasses of history, like President Abraham Lincoln, or you'd prefer characters like The Avengers, or the cast of Game of Thrones, you'll find them all at the Character Conversions Page on Improved Initiative.
Race, Attributes, and Traits
We, in the modern-day, are used to our politicians being boring. They come from wealthy families, attended prestigious schools, and they're typically seeking office for a variety of pedestrian reasons. Some of them want to help the people, some of them want power and prestige, but overall they tend to be pretty bland when it comes to badassery (with a few, obvious exceptions).
That's why, when you find out more about Teddy, the word "politician" never really enters your mind. In his youth he worked a variety of hard, dangerous jobs. These included cattle rancher, combat veteran, deputy sheriff, and professional explorer. That last one is a job that doesn't really exist anymore, and we're pretty sure no one could do it nearly as well as Teddy did. In fact, it was only through some serious backroom deals that he was made the governor of New York by corrupt politician Thomas "Boss" Platt in the first place. When Teddy decided he was going to govern his way, rather than the way Platt told him to, he was shunted up to the Vice President's slot under McKinley. McKinley was assassinated 6 months later, and that was how Teddy started swinging heavy with his big stick diplomacy.
So, knowing all that, the most accurate race for President Roosevelt is human. And, though he was born with asthma and was far from the most physically active child, his pursuits as a young man and adult (such as giving a speech with an undressed bullet wound in his chest) required legendary toughness. Additionally, though he was a plainly spoken man, he was compelling to listen to, even if he was brusque at times. Ideally, you'll want his biggest attributes in his physical stats, and you'll want wisdom, charisma, and intelligence in that order.
When it comes to Teddy's traits, you need to pick which parts of his history you're trying to represent. For example, if you want your version of this character to focus on being a leader, as he was among the first U.S. Volunteer Cavalry Regiment, then traits like Natural Born Leader (+1 morale bonus on Will saves for all cohorts, followers, and summoned creatures, as well as a +1 on your Leadership score if you take the feat) would be a worthwhile investment. If you'd rather focus on Teddy's skill as a soldier and a gun hand, though, then traits like Black Powder Bravado (once per day when you miss with a gunslinger deed that requires an attack roll, you may re-roll that deed), or Armed Grit (+2 trait bonus on saves against fear, and the DC to intimidate you goes up by 2 when you have a firearm drawn) are probably more in line with what you're thinking about.
Remember, when it comes to traits, be accurate, but also pick traits you're going to get a lot of use out of.
Theodore Roosevelt was a man of many, and varied talents. And while he was a statesman, a leader, and a politician, he's most famous as a soldier, woodsman, and hunter. Roosevelt kept a pet badger that was thrown at him by an admirer in Kentucky, and it wasn't uncommon to see dangerous predators in his proximity while he was attending to White House affairs. Of course, the most obvious class for Teddy is the ranger, but not just any ranger will do. In fact, because Teddy is a man of such iron-clad badassery, I recommend a combination of two ranger archetypes. The Trophy Hunter (Ultimate Combat 67) and the Skirmisher (Advanced Player's Guide 128).
From the Trophy Hunter we gain Improved Tracking, which allows Teddy to study a creature's tracks, and learn things about it before ever coming face to face with the creature who made those tracks. We also gain the Amateur Gunslinger feat for free at second level, and we can take any grit feats or deeds thanks to Firearm Style. We also gain Hunter's Aim, which means all attacks with firearms are touch attacks within the first 2 range increments, instead of one. From the Skirmisher we trade out our spells, and instead we gain Hunter's Tricks, which are abilities that give us and our allies bonuses in certain situations. Tricks like Distracting Attack, Defensive Bow Stance, and Hateful Attack are all useful tricks to have up your sleeve.
It's also important to remember that you keep your Favored Enemy and Favored Terrains. Teddy was a hunter of men, as well as a hunter of animals, and he was always at home in the forest, as well as in other locales. What he's been hunting, however, will depend on his history within your game world, and this particular campaign.
But what about Teddy's known enthusiasm for unarmed combat? He was a pugilist, and a student of several martial arts. For players who want to add that element into the build, I recommend a single level dip in the Brawler class. This gives you unarmed strike damage, martial flexibility, and the ability to go hog wild if you want to punch with one hand, and shoot with the other.
Skills, Deeds, and Feats
Teddy was a man of many skills. Fortunately, a human with ranger levels gets a minimum of 7 skills (assuming you don't have a negative Intelligence modifier). So, assuming the worst, you definitely need to take Survival, Ride, Stealth, Handle Animal, Knowledge (Geography), Knowledge (Nature), and Perception. If you have the skill points to burn, then you might also want to take Climb, Swim, Intimidate, and Diplomacy. The last one won't be a class skill, unless you take a background trait to make it one.
Now, for feats. Feats are going to be decided based on what you're going to be doing most with your Teddy, so you need to choose the ways you want your Teddy to excel. For example, if you're going to be a shooter, then you'll definitely want to invest in Point Blank and Precise Shot (Core Rulebook 131), Exotic Weapon Proficiency (Firearms) (Core Rulebook 123), and possibly Rapid Reload (Core Rulebook 132). At that point you need to decide if you're going to be more of a one-shot kill sort of shooter, by taking feats like Vital Strike (Core Rulebook 136) and Deadly Aim (Core Rulebook 121), or if you would rather fill the air with as much lead as possible using feats like Rapid Shot (Core Rulebook 132), counting on resolving attacks against your enemy's touch AC for your shots to strike home.
You can supplement your feats with Gunslinger deeds, as well, thanks to your Trophy Hunter archetype. For example, instead of taking Vital Strike, you could take the Dead Shot deed, and combine it with Deadly Aim to produce truly disastrous damage when you pull your trigger. Alternatively, if you want to be more of a monkey wrench than a damage dealer, the Targeting deed can make it so you can shoot your enemies' weapons out of their hands, or blow their legs right out from under them. Of course, the number of times you can do these things is limited by your grit pool.
If you find yourself with open feat slots, because you're focusing on your deeds more than on regular feats (and you've taken Extra Grit to make sure you don't run out of badass), there are some others you might want to add in for character background. Endurance and Diehard (Core Rulebook 122) are staples of Roosevelt's life, like when he rode over 100 miles without rest or sleep while he was in his 50s, because he'd received a letter from a soldier complaining they had to ride 20 miles while on maneuvers. Leadership (Core Rulebook 129) is always useful, though you might not be able to convince your DM to give it to you. And if you do intend to be a mounted character (though your horse/moose won't be particularly durable, unless it's also your cohort), you might want to invest in Mounted Combat and Mounted Archery (Core Rulebook 131).
Equipment and Story
President Roosevelt was a man known for his swagger, his fearlessness, and his bullet-proof mustache. However, he didn't have a signature piece of weaponry or armor. While he walked about the White House with a revolver on his hip, and carried all the standard-issue gear a soldier would have received while deployed, he wasn't famous for any one item in particular. So, it's up to you to decide what kinds of weapons and armor your Roosevelt is going to be packing when he goes out into the wild.
The other important decision you need to make, as the player in the driver's seat of this madman, is at what point in Teddy's life are you stepping in? Is he a hunter and rancher with dreams of stepping in to power? Is he a regional governor who isn't afraid to get his hands dirty? Is he a secretary in the armed forces, issuing commands with the same gusto he used when he was still in the field with his own troops? Or, because you're starting out in a high-level campaign, have you ascended to the highest office in the land, and now need to get out from behind your desk to take care of business yourself?