This, without a doubt, was my craziest idea. Fly from Pittsburgh to LA, buy a vehicle, then drive it back over the course of a week. All in the pursuit of a rust free (or as close as possible) 99 or 2000 Cadillac Escalade. What convinced my wife to go along with such a meshuga scheme? She would get a vacation, and I would get a full size SUV out of it. The trip would not be too expensive – I had enough hotel points with Hilton to get 4 out of the 7 nights for free, and with my Delta Amex companion ticket, the flight would be mostly covered.
When I last wrote up a vehicle, I had purchased my parents’ 2012 Escalade Platinum in the fall of 2023. Since then, we traded in my wife’s 2017 XTS on a 2021 XT5 – and I sold the Escalade, thinking we wouldn’t need two utility vehicles and I could get along with a sedan.
Boy, was I wrong.
Turns out I missed sitting up high and having cargo room at my disposal. Our XT5 is a wonderful crossover, but after the first few road trips I realized it was not as roomy as I thought it was going to be.
I cycled thru a couple of daily drivers between spring 2025 and now – a 97 Buick Riviera, 05 Lincoln Town Car, and 05 Cadillac DeVille. The Riv was fun, but on the highway there was a wind noise I couldn’t get rid of. The Town Car gave way to the DeVille – the Town Car is a tank, but I enjoyed the quickness of the Northstar along with the tighter feel of the G body.
So after seeing YouTuber Tyler Hoover grab a 1st gen Escalade from Southern California, and not wanting to roll the dice here in the Salt Belt, I started looking in the LA area for a nice first or second gen example. FB Marketplace served up the one I went with – this two owner 2000 Escalade with 170k miles – but the interior looked neat as a pin, and it came with a stack of service records.
And the game show geek in me loves that it came from Casa de Cadillac, where all the classic “The Price is Right” 80’s Cadillacs came from. Negotiated a price that would include putting new tires on, as he wasn’t sure of the age of the rubber on the rims at that moment.
Showed the vehicle to my wife, and she approved – so we’re off and running! Sent a deposit and began planning our trip. We’ve always wanted to see parts of the old Route 66, along with visiting places like Palm Springs and San Diego.
Our latest addition is a vehicle that has gotten some love here over the years, mostly due to just how quickly it came together after years of Cadillac brass proclaiming that there wasn’t going to be a Caddy truck sharing the lot with Eldorados and Sevilles. But with the Navigator helping Lincoln outsell Cadillac for the first time in a decade, the powers that be quickly pulled a rabbit out of their hat and converted the GMC Yukon Denali into the Escalade. The Car And Driver review of the 98 Yukon Denali had an interesting quote from GM brass – “Eighty percent of regular Yukons were sold with every available option,” says GMC assistant brand manager for product Kevin Stein. “We needed something for the customers to step up to from the regular Yukon.” That would be a big flashing neon sign for me that there needed to be a Cadillac grade full size SUV yesterday. Car And Driver had Brock Yates review the 99 Escalade, and his closing lines could have been the entire article “In sum, if you are a Cadillac loyalist with nearly 50 grand in your pocket (including taxes and licensing) and in desperate need of an SUV to counter the sneers of your Lincoln-owning fellow dubbers, the Escalade is for you. For the rest of us, a vast array of alternatives waits in the marketplace.”
I can already hear the cries of “BADGE ENGINEERING” from the peanut gallery – and while you aren’t wrong, the GMT400 platform was a much better place to be starting from than the J-car was for the Cimarron. Different leather, standard OnStar, extra Zebrano wood trim on the dash to go with the wood on the steering wheel, Bilstein shocks, and PassKey3 were all yours for a base price of $46,525.
The MotorWeek review of the ’99 Escalade shows the strength of the GMT400, and the Vortec 5700 – despite the newness of the Navigator and it’s 32 valves, the pushrod SBC was quicker with less harshness to go with an overall better ride. I will say that the 1st generation Navigator does have a nicer interior – my high school friend Rob’s parents had one, and it was a nice place to sit. At least until the rear air bags gave out – and they did a few times over the course of ownership.
I did look at one Escalade back home in Pittsburgh, and apparently these are a tough sell due to the lack of a 3rd row compared to later models and the Navigator. However 23,346 copies found homes in 2000, helping narrow the sales gap between Cadillac and Lincoln to only a few thousand vehicles (190,825 vs 193,009).
With all the plans made, we set out for Los Angeles on Saturday morning – the flights were uneventful, and the short layover in Detroit was long enough to grab lunch. We landed at LAX and then Uber’d over to the warehouse where the Escalade was parked. It was strange seeing this imposing hulk next to a 30’s Rolls Royce and 80’s Ferraris – but the seller couldn’t have been nicer. We fired up the Escalade, made sure nothing was leaking, set the AC to MAX, and headed off to check into hotel number one for the evening.
But first, a gas station as the gauge was at a 1/4 – and filling up the 30 gallon tank made me thankful to have my Amex handy. The revised EPA estimates of 11 city and 15 highway on regular are pretty accurate – the best I did on a stretch of highway was 15.3.
Cruisin’ around LA was fun – by happy accident, it was Coachella weekend, so traffic was lighter than expected. One of things I didn’t test before driving off was the Bose Acoustimas sound system – I tuned to K-EARTH 101.1, the legendary former oldies station with jocks like The Real Don Steele, Humble Harve, and Shotgun Tom Kelly…and proceeded to hear Tupac “California Love”. Very fitting, but another not so gentle reminder of what changed since my last visit to LA in 1999 as a kid. But all the speakers were working, as was the console subwoofer.
The weather also gave me a chance to test the wipers – and they say it never rains in Southern California!
On Sunday we spent the day driving around after doing the Warner Brothers studio tour – I enjoyed getting up to Topanga Canyon, however the Escalade is not exactly as fun to sling around curves as a Mustang. It also was a good way to test the brakes – and let me know that they needed some work once we got back to Pennsylvania.
Malibu was fun, if only because I am a fan of “The Rockford Files” and getting to see some of the shooting locations was a blast.
That night we went from driving in a boat to staying on one in Long Beach – the Queen Mary opened as a hotel in 1971, and we had a lovely time exploring the ship. Also on board was various high school groups…including one from Bucks County PA. Funny travelling across the country running into people a few area codes away from home.
Monday we travelled down to San Diego to take in some more sights and visit friends before heading East. It was then I took a closer look at the tires in the bright sunlight, and discovered that they were starting to show cracks from dry rotting. While eating lunch I found a Discount Tire that had a reasonable set in stock a few minutes away. My wife stayed behind to explore Old Town while I had the new tires installed – the last thing I wanted was a blowout somewhere in the desert. An hour or so later we were back on the road.
Palm Springs was our destination that evening, and our only regret was not being able to stay longer. The midcentury modern architecture everywhere, and classic cars, were a treat. Also gave me a chance to compare our Escalade to a contemporary one in the parking lot.
But we were off to Sedona Arizona to enjoy the red rocks and make our way to Route 66 – I had never been to this part of the West, so I couldn’t get enough of the scenery. The vast expanses of glass in the Escalade helped to take in the scenery along the way.
With the tires taken care of, I could confidently do highway speeds – but my desire to not get a ticket…and maybe save on gas…kept me in the right lane for most of the trip.
We kept heading north to Flagstaff where we met with I-40 and headed east to hit up as many Route 66 tourist spots as possible. And enjoy as much good food as possible – if you find yourself in Holbrook AZ, I recommend Colonel Mustards for a great Chicago style hot dog. We also stopped by the Wigwam Hotel to snap a few pictures, and the infamous corner in Winslow that The Eagles sang about.
Albuquerque was up next, with us staying in the historic Hotel Andaluz. I’m not a fan of having to valet park, but it was worth it for such a unique hotel. We had dinner at El Pinto, and it was the best Mexican food outside of California on our trip.
With us front loading the Western states, we were starting to Cannonball it back East after this – next stop was OKC, with Amarillo Texas in the middle. We had to stop at The Big Texan for lunch, along with the Cadillac Ranch and the Slug Bug Ranch. And Buc-ees of course.
The Escalade took it all in stride, but the strong cross winds were a challenge at times due to some of the worn front end parts that would be replaced when we got home.
From OKC we headed to St Louis, with a detour to Norman OK so I could visit the hometown of James Garner and see his statue.
On a long road trip like this, the virtues of the Escalade (and the GMT400) really shine. Big comfy captain’s chairs up front, plenty of cargo room in the back, even with the rear seats up, and a big gas tank for highway cruising means you only stop every 300 or so miles to fill up. While the highway ride is not quite a Brougham or Park Avenue, it is relaxed and smooth enough you aren’t hurting after a day behind the wheel.
We made it home after 3,003 trouble-free miles (aside from tires and some brake noises), and reminded me why I’ve owned three other GMT-400 vehicles. Good highway ride, comfortable seats, great utility, and the Vortec 5.7 provides enough oomph to keep up with modern traffic.
Repairs so far? New front and rear brakes, windshield wiper motor, new radiator, and a new alternator. The seller gave me the radiator, commenting that there was a coolant leak but wasn’t the radiator at the time. Lucky for me! And I did the work myself to save money – easy enough job given the space under the hood.
I put the truck to work hauling around my DJ equipment – I did two car shows over Father’s Day weekend – and it was great just being able to throw everything in the back and go instead of playing Jenga fitting things in.
The styling, inside and out, is also one of the reasons I love these trucks. The GMT 400 might be the best thing to come out of GM styling in the Rybicki era (It first arrived in 1988, but it was styled before Chuck Jordan took over from Irv Rybicki in October 1986.) The cladding and tweaked front end for the Yukon Denali/Escalade add to the look without looking Pontiac excessive. My only critique would be the dash plastic aged like milk, as do most 90’s GM vehicles.
Cadillac would see much more fame and fortune with the next generation Escalade that debuted in 2002 (they skipped a 2001 model), the “Art & Science” GMT800 that everyone from hip hop & pop artists to athletes had to be seen in one. While this is not what anyone would consider the ultimate Escalade, it did put Cadillac on the path back to relevancy and was an aspiration vehicle. At least for this Millennial.
Next up for this example is rustproofing and a front end rebuild – and I’ve learned my lesson about not keeping a full size SUV around.
Related CC reading:
2004 Cadillac Escalade – Assault With A Gilded Ladder, GTWTW Pt.3
2000 GMC Yukon Denali – Denali All Thing, GTWTW Pt.5
I remember being surrounded by this generation, although in Chevy/GMC versions. These were really nice vehicles, and it is great to see you find a really nice one. When these were new, I kind of pooh-poohed them as devices for GM to vacuum money from snobby buyers, but now I can appreciate how the interior upgrades really make a nice vehicle nicer. Enjoy!!
That Rockford shirt is glorious.
This is the only Escalade generation I like. It’s like the fully loaded Suburbans around since the 70s nicknamed “Texan Cadillacs.” They could have had a great hit in the Cadillac division decades ago. I love the color on yours, too.
Wow. Congrats on the purchase and on the successful and uneventful cross-country trip back home to the rust belt. This vintage of GM truck is under-appreciated, but they’re so much better and easy to work on than today’s overly-complicated and trouble prone equivalents.
Doing something like this (except with a big ’60’s or 70’s convertible) was always on my un-official bucket list until I got sick.
I’ve often dreamed of doing exactly this – buying a car and taking a road trip to return, sounds really fun. Thanks for sharing your story with us!
Picking up a car from a distant location and then enjoying the drive home is a fabulous way to experience a new or new to you car, I’ve done it twice now – The Audi S6 wagon from Beaverton, OR back home to Oakland, CA and then again with the Porsche 911 from New Jersey back to Colorado. No better way to get to know a car quickly and so much better than just buying a car and then…commuting.
Having owned a Chevy Tahoe of this generation I have to say it was quite a good experience. Even when something did go amiss, it was generally cheap and easy to fix and it was exceedingly comfortable, and with almost all parts shared with Chevies built in the gazillions, parts should be plentiful and cheap for decades to come. I think the main reason we sold it was the lack of good child seat anchors (fine for 1999, not so much for 2010-ish), but now in 2026 it’d be a fine vintage ride! Ours was loaded up enough for us, but the Cadillac is likely a whole ‘nother level, for a nice one these days I can’t imagine the price is really much different if at all vs a Tahoe or Yukon.
Enjoy the new ride!
Good way to turn car buying into a mini-vacation. You hit a lot of familiar high points along the way. Enjoy your ‘Lade.
A few months ago I read a critique of the Queen Mary hotel and it wasn’t doing very well and losing money. I hope they can keep it going.
Somehow the first-gen Escalade escaped the “overpriced Chevy Tahoe” stigma that quickly sunk the Cimarron (“overpriced Cavalier”). Probably because a full-size, V8 SUV fit the Cadillac image much better than a wheezy four-cylinder 88hp subcompact.
I was in Norman, OK for a few days and knew nothing about its history; I was there for work.
No need to guess how old tires are; there are date codes stamped into the outer sidewall (or the inner sidewall if they were mounted backwards).
In Amarillo at The Big Texan did you do the 72 oz steak challenge? If not, was anyone trying?
https://bigtexan.com/pages/72-oz-steak
That’s what I wondered too. We ate at the Big Texan a few years ago, and there was someone doing the 72 oz. steak challenge – he’s the guy sitting alone at the podium table in this picture below. He was able to complete it, too. Even without that as background entertainment, the Big Texan was a fun experience!
I did not, despite “Big” being in my name LOL
Nobody else was either, but it was still a fun place to visit.
Steak was pretty good too
Wow – what a great trip! And the Escalade looks remarkably clean for having 170,000 miles. I’m glad it all went well for you; not just mechanically but also with registering the car. I’ve heard that a lot of states make it very hard for non-residents to get temporary plates, which makes this kind of thing very challenging sometimes. I hope I’ll be able to get out West again sometime; each time I’ve been there, I’ve enjoyed the western US more than before.
There’s a lot about big SUV’s that I can try to convince myself to not like. And my one experience driving a GMT400 Tahoe was not very pleasant, at least compared to the fairly new Toyota Land Cruiser 80 that we had at the time. But a rental experience in a Pathfinder Armada and later in a newer Suburban almost made me a fan. So comfortable and roomy; really only parking in my community and of course fuel price would deter me. But a cross country trip in a comfortable and new-to-you car is always wonderful. Thanks for posting this and enjoy your 25 year old classic.
Is there a story behind buying it in California when it had an Arizona plate?
He had it registered and titled in Arizona since it is cheaper than California is what he told me. Not sure how much cheaper, but I guess if you have a bunch of vehicles it adds up.
Glad to hear that you got a great truck and had a great trip. While I’m part of the other camp; Ford/ Lincoln Navigator, I know lots of people with Chevys and GMCs. Big Suvs are probably the nearest thing that lets you experience what the big land yacht cars of the ’50’s and ’60’s were like when they were still new.
The fancy GMT400 was a winner but we live at the opposite end. My son has a rare base trim 99 3/4 ton Suburban with vinyl bench seats, hand cranked windows and the W/T grille with two square headlights. It works for a living as his tow rig hauling car trailers and as an occasional delivery truck for work. It’s sturdy, reliable, hard riding and thirsty which is why he tries to only use it when he needs it. Personally I have an F150 for truck stuff that’s somewhat plush with soft springs and leather seats but I need the 8′ box more than the payload