My ‘Jeep Cherokee From Hell’ Drove To Chicago Flawlessly And Reminded Me That Love Is All About Timing

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As I cruised up Lake Shore Drive through Chicago’s prettiest neighborhoods on a perfect 75 degree sunny day, I realized that the Jeep I had just sold was perfect. It was everything I had hoped it would be when I bought it back in 2018: The 4.0-liter felt powerful, the five-speed manual shifted beautifully, the interior was gorgeous, the paint glistened, that chrome grille reflected onto the streets ahead. Four years ago I wrote that “I Went Through Hell to Buy This 1991 Jeep Cherokee But Now I Have My Dream Car.” In the ensuing years, that “dream car” became my nightmare, but on Sunday, finally, it become my dream car again. But it was too late.

I’ll allow my younger, 26 year-old self to explain how thrilled I was to have bought this 1991 Jeep Cherokee in September of 2018:

It’s not perfect, and I had to go through hell to get it (with the price ballooning from a song to $900 to $1,700 to $2,000), but in the end, I own my dream Jeep—an unmodified, rust-free, manual transmission, 1991 (the first year with the more powerful and reliable Chrysler fuel injection system and the improved cooling system), vent window-equipped Jeep Cherokee Laredo.

I need nothing more in this life.

Reading that last sentence, “I need nothing more in this life,” reminds me of just how much of a rollercoaster car ownership can be. I was so excited to own my very favorite version of my very favorite Jeep, but then the machine kept breaking. In my previous article, I listed all the parts I’ve had to replace in the 100-ish miles I’ve ever driven this Jeep since buying it. Allow me to paste that list here again, but with more recent additions included:

  • Replaced cylinder head
  • Replaced radiator
  • Replaced thermostat
  • Replaced water pump
  • Replaced upper control arm (driver’s)
  • Replaced front left fender (which I had professionally painted)
  • Replaced front left fender flare (which I had professionally painted)
  • Replaced front left fender liner
  • Replaced front bumper (which I had professionally painted)
  • Replaced rear bumper (which I had professionally painted)
  • Replaced front axle
  • Replaced front axle u-joints
  • Replaced front ball joints
  • Replaced steering tie rod ends
  • Replaced steering drag link
  • Replaced steering intermediate shaft
  • Replaced steering box
  • Replaced control arm bushings on front axle
  • Replaced front axle seals
  • Replaced front axle disconnect motor
  • Replaced front wheel bearings
  • Replaced front brake pads
  • Replaced front left wheel
  • Replaced all four tires
  • Replaced all four shocks
  • Replaced rear leaf springs
  • Replaced driver’s seat
  • Replaced driver’s door check-strap
  • Fixed rear hatch interior trim
  • Replaced front windshield wiper motor/transmission
  • Replaced engine computer
  • Replaced radio
  • Replaced power steering pump

What an absolute nightmare this thing has been. That’s over 30 fairly-significant parts replaced, and the sad thing is: I never really even got to enjoy the Jeep. Well, not until Sunday, the morning after I arrived back in Michigan from California, where I drove the Ford Bronco Raptor (more on that soon!).

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Of course, I didn’t leave when I should have on Sunday, not just because I forgot to set my alarm, but because of course the XJ just had to kick me in the ass one last time, for ol’ times sake. During my final shakedown to make sure I was delivering Tracy a machine that wouldn’t let her down (she’s an awesome woman who sold me a fantastic Land Cruiser a while back. I owe her!), I noticed a loud squeak pretty much anytime the Jeep wasn’t in a steady-state motion condition (i.e. anytime I hit a bump or accelerated/decelerated). I slid under the Jeep to find a completely obliterated upper control arm — the bushing wasn’t even connected to the damn arm anymore, so the thing was just rattling around, squeaking, and barely fulfilling its function of preventing the axle from twisting.

Luckily, I had a new upper control arm sitting around, but installing it was far more of an ass-pain than it should have been. The clearance between those control arm mounts and the front steering parts/axle tube just made removing the control arm bolts a chore. What’s more, once the old arm was out, getting the new one’s holes to line up properly required some careful use of the floor jack. It wasn’t that difficult of a job, but I had anticipated it taking 30 minutes, and it took two hours. And that delta between expectation and reality can be a mood-crusher.

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It was a late start, but I was glad to finally be heading south on I-75 and then west on I-94 across Michigan, a state whose beauty I, a guy living in the most suburban sprawl-y place imaginable (Troy), forget about all too often. The Jeep drove wonderfully. The AX-15 five-speed’s shifts were crisper and tighter than any five-speed Jeep transmission I’d ever driven. The straight-six’s prodigious torque, tasked with pushing along a lightweight 3,350 pound box, made acceleration feel genuinely quick. Highway speeds were no problem; the new leaf springs, shocks, and tires I’d installed, along with the new driver’s seat, made cruising along at 75 MPH legitimately comfortable.

The temperature needle stayed just counter-clockwise of 12 o’clock thanks to the new cylinder head and radiator I’d bolted up, the brakes worked great thanks to the new pads I’d thrown in, and the steering felt buttery thanks to the new steering pump I’d installed,

The XJ that I’d been dreaming about since my youth was finally dialed in.

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When I stopped for gas and water, I couldn’t help but look back at that beautiful profile. Recently repainted and rust-free, the chromed-out XJ Laredo looked like a million bucks, and for the first time under my ownership, finally drove like it, too.

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Fuel economy was less than optimal at about 19 MPG, but I didn’t care. I spun open the vent windows, rolled down the main glass, and let my arm dangle along the vehicle’s beautiful sheetmetal as 75 degree air blew across my face and sun shined through the humongous, beautifully untinted greenhouse. The shores of Michigan sat to my right as I shifted between gears in Chicago’s traffic. I passed gorgeous neighborhoods, saw kids graduating from Northwestern University, and ultimately wound up in the stunning village of Wilmette, about an hour north of downtown.

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There, I dropped off  the XJ at Tracy’s mechanic, who will fix the Jeep’s air conditioning before Tracy returns from her visit to her home state of Oregon, where the Jeep grew up after her dad ordered it from the factory in 1990.

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It’s wild to think that I sold what I considered the perfect Jeep after going through so much to obtain and repair it. But the Jeep hurt me too badly, and the scars are too deep. In the early days, when I first picked this machine up, I was excited, as most are when they start a new automotive relationship.
Here’s a gorgeous machine that I scored for a song, let me do a few repairs and then keep this vehicle forever,” I thought.

It was exciting, even though I knew what I was getting myself into. I realized that the Jeep had some significant flaws; it had been in an accident that had compromised the driver’s side front fender and the front axle. The problem was that, even after replacing these, the Jeep kept letting me down. The power steering pump leaked, the four-wheel drive vacuum motor went out, the wiper motor died, the steering box was toast, and on and on.

The relationship soured, and though my drive to Chicago made me realize just how amazing this Jeep is, the reality is that I can never love it. I met it at the wrong time, when it was going through some trouble — struggling with problems that it leaned too hard on me to fix. And while, in the end, I did fix these problems, and the Jeep is everything I could have ever wanted, the toll on me was tremendous.

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Loving a car is all about the balance between the great moments you’ve enjoyed with that vehicle and the hardships it has caused you. You want the former to outweigh the latter, of course. And while yes, I could probably take the black XJ on some epic trips, the problem is that I’d have to live 200 years for the joyful moments to outweigh the misery.

It’s for this reason that I’m going to stick with my O.G. Jeep Cherokee, Ol’ Red — a 1992 automatic that’s a bit rusty, and more than a bit broken. It needs a rear axle and possibly a new cylinder head. But it’s okay, because this Jeep changed my life. It taught me to wrench, it helped me get my dream jobs, and it’s taken me on some of the greatest off-road trips of my life. It has so much goodwill saved up that I’m happy to fix it back up. I owe it.

You see, the red Jeep and I met at the right time. I needed it when I was in college, and it was there for me. And though today, in June of 2022, the ’91 is in objectively better shape than Ol’ Red, I will gladly bleed, sweat, and cry for my trusty red box. I have never once complained about working on it, because you don’t complain about helping out family.

It’s a feeling that I know Tracy understands; she’s buying back a 30 year-old car that she learned to drive stick on many years ago. She can love it like I never will, and since I just bore the brunt of its wrath, I think her love for this machine will last for decades to come.

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44 Responses

  1. I remember first reading about this jeep years ago. It was one of the first articles by you I ever read. Despite all the hardship you went through exorcising the demons put of it, it’s a beautiful story! I’m glad you had that jeep and it almost seems like you were ment to get it back to Tracy! You went at it with love and now she gets to have that important piece of history for her back!

    If I could just figure out who bought my grandfather’s ’67 impala, the car that made me love cars, I would be over the moon.

    Thank you for sharing all of it!!!

  2. I seriously hope this is the last we hear about that hunk of shit! ha.

    Don’t get me wrong, it was always a cringingly entertaining read, but good gravy. I do hope it treats the “other” Tracy well, though. I kinda doubt it since it’s still a JYD, but hey, sometimes people win the Powerball…

    I’m still curious about the P/L tally on that thing, DT.

  3. Glad you got it delivered, hope it serves her well.

    I definitely know how it feels to get burned by a car, and lose your desire for it.

    I also know how it feels when a car pulls itself and you through incredible adversity, through storms of many kinds, earning its place in your heart, as your Red Box has done for you. May you enjoy many more miles in it.

  4. “Allow me to paste that list here again, but with more recent additions included:

    Replaced cylinder head
    Replaced radiator
    Replaced thermostat
    Replaced water pump
    Replaced upper control arm (driver’s)
    Replaced front left fender (which I had professionally painted)
    Replaced front left fender flare (which I had professionally painted)
    Replaced front left fender liner
    Replaced front bumper (which I had professionally painted)
    Replaced rear bumper (which I had professionally painted)
    Replaced front axle
    Replaced front axle u-joints
    Replaced front ball joints
    Replaced steering tie rod ends
    Replaced steering drag link
    Replaced steering intermediate shaft
    Replaced steering box
    Replaced control arm bushings on front axle
    Replaced front axle seals
    Replaced front axle disconnect motor
    Replaced front wheel bearings
    Replaced front brake pads
    Replaced front left wheel
    Replaced all four tires
    Replaced all four shocks
    Replaced rear leaf springs
    Replaced driver’s seat
    Replaced driver’s door check-strap
    Fixed rear hatch interior trim
    Replaced front windshield wiper motor/transmission
    Replaced engine computer
    Replaced radio
    Replaced power steering pump”

    So… are we going to go ahead and replace “The Ship of Theseus” with “The Jeep of Tracy”?

  5. David, I’ve bought and sold a shit ton of cars. From the mundane to the magnificent. And I’ve learned at least two things during those literal scores of flips.

    1.) There’s nothing and I mean NOTHING like the adrenaline rush that is the thrill of the chase. Cruising listings is definitely like searching for a fix and you get a little A-jolt when you find “the one.” Message the seller, find out it’s actually still available. Ask them the pedantic questions only car nerds know…get vague, but reaffirming answers that reinforce the need for this car. And now you’ve got another dose of adrenaline. This continues throughout communication, between the buyer-seller courtship, the pictures, the description, the making of the appointment. Inspection, test drive, the horse trading and negotiation. Right up until the waves of euphoria recede and you pull your new shitbox into the garage and wonder what you’ve gotten yourself into, what you fooled yourself into thinking is fine but probably isn’t and now it’s your problem.

    Good times.

    2.) The car your selling drove decent while you owned it. I mean, you took care of it, fixed the problems, future-proofed the non-existent ones, and generally gave it more care than it really deserved. Shoot, it might have even driven “good.” But let me tell you now, it is an immutable, universal tenet of science: your car will never drive as well as it does than on its last drive, whether for old times sake or if you’re delivering it to a dealer or a buyer. Tell me I’m wrong, but you’re going to be lying to yourself.

  6. You probably already know this, even if you won’t admit it to yourself, but if you weren’t always distracted by too many vehicles that pulled your attention away from the good stuff, you probably would have had this sorted years ago, and enjoyed many many miles in it. Instead you fritter the hours, days, and ultimately years away on piles of rusty garbage. Your automotive/time management triage skills are … Suspect.

    How else do you explain hating the best vehicles in your fleet?

    1. Tired of lying in the sunshine, staying home to watch the rain
      You are young and life is long, and there is time to kill today
      And then one day you find ten years have got behind you
      No one told you when to run, you missed the starting gun

      And you run, and you run to catch up with the sun but it’s sinking
      Racing around to come up behind you again
      The sun is the same in a relative way but you’re older
      Shorter of breath and one day closer to death

        1. I’m with David on this one, I’d take the J10 over the nice-looking Cherokee in a heartbeat (provided the J10 came with the bed cover). The nice Cherokee would wreak havoc on my mental health just from the anxiety of driving with the constant feeling that something could break down at any moment.

  7. It is about timing. I’m in a much better spot to appreciate my 84 Rx7 or my 64 triumph spitfire but cannot afford either now! That xj is in the place it belongs and frees up more attention and funds for the rest of your fleet.

  8. Having driven my last two cars to the junkyard I understand completely!
    I gave them one last hard run and said thanks, then I walked away with a heavy heart knowing that I could have done more to keep them running a little longer, but realizing that it was only postponing the inevitable. 🙁
    I believe you did the right thing,
    clearly this was not your Jeep hence your reluctance to commit to it fully.
    Loved the story, and the outcome, thanks.

  9. I feel like this cautionary tale is a perfect example of how cars end up on Craigslist needing “just a few simple repairs”. At some point the owner has accepted that the repair list is infinite and no matter how many they make there will always be more. 😉

  10. Some vehicles are simply cursed and this Jeep is one of them. Hell you had to replace yet ANOTHER part before delivering it. Hopefully, Tracy knows a priest who can perform exorcisms because this Jeep needs one. David, be glad you’ve washed your hands of this rolling money pit.

  11. David, I understand your pain in a lot of ways. I have held on to cars too long because I am a sentimental fool, and I still cruise listings looking for cars similar to ones that I once had.

    Here’s the bottom line: no matter what you find, you’ll never fill the hole that getting rid of a once loved car leaves. You can try, but it’s like dating someone that looks like a lost love — it just ain’t the same. No car is ever as good as you remember it being.

    And the rose-coloured glasses….every time I think about another BMW, I run down the list of things that went wrong with my 540i6. It takes a while, but usually when I am about halfway through, the bile of anger starts rising in my throat again. Then I look at my kids and remember I just don’t have time, or for that matter the emotional bandwidth, for that crap anymore.

    So, if I do get a toy/project, it will be something new, so that I can learn new things on a different car. Better to move forward.

  12. There’s an ’86 El Camino in my family that treated me much the same as this Jeep did.
    My uncle owned it from new, my Mom bought it from him shortly before I went into the USAF, and then I drove it for two years or so. It was my uncle’s weekend car and it is one of the nicest looking vehicles I’ve ever owned, interior was (and still is, actually) immaculate, he had it repainted a year or two before he sold it to my Mom. Pure 80s glory.
    In the two years I had it it was broken about half the time, partially due to me just learning to wrench at the time, but mainly because the 4.3L V6 in it was hacked on by some idiot mechanic at the behest of my uncle who wanted to increase the HP without swapping in a V8. To give an example of the hackery, Mechanic Bubba removed the TBI and slapped an Edelbrock intake and carb on it and zip tied the choke half-closed so that the idle was somewhere between 1500-2000 at all times. I slowly undid a lot of Bubba’s “fixes” and it got me up and down I-95 from Florida to D.C. on leave a couple times a year, but every time I had some reason to struggle with it before it made the trip.
    Halfway through my first enlistment I bought one of my forever vehicles, a ’93 F150 with the 4.9L and proceeded to put ~250k miles on it over the better part of the next two decades. The El Camino went back to Mom for a while.

    The El Camino stayed in the family, bouncing to a cousin of mine until my Mom bought it back, and it appears that it will be coming back to me at the end of summer (gone is the 4.3L V6, in its place is an LS3.)

    Its… complicated figuring out how I feel about it coming back to me. Supposedly a couple good shops have worked on it and have ironed out the LS swap and other issues, but… its still the vehicle that burned me multiple times.
    Maybe now that I’m older, wiser, and an engineer I’ll be able to keep the ship afloat?

    We’ll see.

  13. I wasnt aware Tracy had owned this in the past. What a neat ending.
    I hope it doesnt cause her trouble.

    I know you fixed a ton of stuff, but after reading of the control arm problem i’m having serious doubts ! How was that missed before?????
    Is this a Michigan thing? Are cars there so universally rusty that everyone accepts carnage underneath?

  14. The last few paragraphs are some of the most well worded ways of explaining automotive love. It’s about history, more importantly how that history has affected you. It’s why when someone sells their “old faithful” it hurts, because that rock of your life is gone but selling a problem child is like cutting loose an anchor. It doesn’t matter the rarity or the importance of the combination of their parts. Not many people can be lucky or rich enough to get what they exactly want. It’s cars like your red XJ that let us appreciate the cars we do find and get to cherish them even if they’re not perfect. Would I consider my car the perfect spec if it had the standard transmission? Sure, but in the end that really doesn’t matter if I was never going to find my perfect spec or afford it. I’m happy I got my car, because even though the transmission holds it back it still makes me smile after every photo I take of it. I’m smiling because of the history of that car even in my short ownership so far, it hasn’t been exactly smooth, even considered selling it out of frustration but I didn’t and I’m glad. I hope that I built the same love as you do D.T. for your red XJ in the future, because that’s really all one can hope for from a car. To have an unbreakable bond with a hunk of metal with 10 times the curb weight of (mostly positive) emotional baggage it carries.

  15. Did you enjoy driving past Bahai Temple? I grew up right around there in the house my mom still owns and miss seeing that sucker daily/nightly. Kinda sad I missed another possible opportunity to meet you. Time to let go the idea.

  16. For some strange reason, a car always drives better than ever on the trip to sell it. I remember my ’90 DeVille that I inherited from my uncle. I put over 100k on it, and by then it was starting to have some issues.
    I replaced the exhaust, several bushings, the brakes, and gave it a new set of tires. Shortly after that, some money came in an I was able to replace it with a new car.
    The drive to the dealership was surreal. I swear that old Cadillac was smoother, more powerful, and quieter than it had been since I’d owned it.
    I hope the next owner got good use out if it.

  17. I know how you feel about selling your dream car because it let you down. Just over a year ago I bought a long time dream car, an imported, JDM Toyota Celica GT-Four. It was modified to produce 300hp at the wheels, and I thought it would be amazing. $5k in parts later I dumped it once I had it running right because it pissed me off too much and I didn’t trust it. New owner loves it, but unfortunately it’s been troublesome for him too. I addressed everything I knew needed to be but then more broke. Stupid car. Definitely don’t want another one, and yet… Literally the day after I sold it I almost bought another that was in rough shape and needed a lot of work. That would’ve been another expensive mistake but I still kinda wish I had gone for it

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