Ticket to Ride: Classic Edition

The core trick to getting this is to stall out your opponents.

Start a game vs. 4 Marg Loughbot AIs.

Why Marg? She has a very strong bias against wilds on the field and when faced with having to draw wilds, she'll draw destination tickets instead.

So, start off by picking a couple cheap destination tickets as your starters (you likely won't complete them, making getting the Hobo achievement a possibility too).

For the first part of the game, your objective should be to empty the train car deck. Just keep drawing from the top (unless there is a visible coal car on the field) until the deck runs out. Do not play any routes unless you fear an AI will take them and need to block; Use as many locomotives to complete those routes though (hit RB or LB to swap from black cards to locomotives when highlighting the route).
Eventually, you will reach a point where there are only Locomotives to draw. Don't start playing routes just yet though. With only wilds to choose from, the Margs will keep drawing destination tickets until the deck runs out. While this is happening, either take the wilds or complete routes with wilds.
When the destination deck runs out, the AI will go into panic mode and just start playing what they can to score points. It's at this time, you need to claim the remainder of the black routes, then just lay down trains to finish the game as quickly as possible.
When the game ends, it will be an easy victory as each AI player will have many uncompleted tickets, most likely sending their scores into the negatives. In the game I earned this achievement, the highest scoring AI only had 30 points and was the only one in positive numbers.

This will take you some luck at several stages, and if you don't get the right luck, you will have to bail and restart a few times. I played vs. one Jane Stanbot.

Tickets
There are 27 black train squares. That means you have a maximum of 18 discretionary squares. Remember that when you're picking your two tickets.

Choose tickets that you can complete with 18 or fewer non-blacks. The ideal setup would be if you can make one continuous route out of your two routes. There are some good choices out there. Most routes including Los Angeles, Chicago, and New York have possibilities. For example, Los Angeles-Chicago is worth 21 and can be completed with only 8 non-blacks.

I drew Chicago-Santa Fe (9) and Duluth-El Paso (10), which have some overlap and require 11 non-blacks to complete. With the mandatory black routes, and using 6 of my last discretionary trains for Winnipeg-Sault St. Marie, I ended up with a continuous route of 36, 8 offshoots/orphans, and 1 leftover. This is only one example of a winning setup.

If you can't get two good tickets, bail and restart.

Drawing Cards
The rules for drawing cards are simple:
1. If there are any face-up blacks, draw them.
2. If there are no face-up blacks, draw a face-up joker, if possible.
3. If there are no face-up blacks or jokers, but you can complete a black route, see the next section below for completing black routes.
3. If you there are no black or joker upcards and you aren't completing a black route, but you can complete a required non-black route without using jokers, complete that route.
5. If none of the above apply, then draw two face-down cards.

Completing Black Routes
Use your jokers to complete the orange/black double routes in this order:
3 for Chicago-Pittsburgh
4 for Denver-Kansas City
2 for New York-Washington
Use your black trains in this order:
6 for Los Angeles-El Paso
5 for Montreal-Sault St. Marie
4 for Winnipeg-Duluth
3 for Nashville-Raleigh

Obviously you can also use jokers for the all-black segments, once you've completed the orange/black routes. Don't place Winnipeg-Duluth until you've collected enough trains to also complete Nashville-Raleigh.

Jane Stanbot
While you're going about your business, Jane will go about hers. She will mostly be concerned about monopolizing Helena, Oklahoma City, and Toronto and will not interfere with your plans much. If she does claim one of the routes you need, it is likely to be Chicago-Pittsburgh or Denver-Kanasas City, which is why those will be the first ones you get. If she takes one of your required routes, bail and restart.

Probably at about the same time that you have placed 15 cars and have 12 more to go. Jane will be down to just a few trains. If she has 3 or 9 left, you're probably going to win. If she has between 4 and 8, it will be iffy, and you might consider bailing unless you are very close yourself. She will go from 9 to 3 and then usually keep drawing cards indefinitely until you get below 9 yourself.

My score was 105. That should be enough to win even if Jane completes her tickets, but in my game, the Queen of Helena didn't complete either of hers, so I beat her by 105-52 and also unlocked Dynamite Joe.