By March of 2001, we knew that our G20 was too small to be our family car. The backseat wasn’t bad, but the trunk was smaller, and as new parents, we traveled with a great deal of luggage when we went to see the grandparents in Pittsburgh. The Jetta had a big trunk, but Bobbi couldn’t drive a stick, and I had grown tired of shifting my own gears in DC traffic. Also, the Jetta had 132,000 miles on it, and while it had been quite reliable, it was time for a change. For us, the perfect family car turned out to be the Chrysler 300M.
When we started looking, Bobbi said she didn’t want a station wagon, minivan, or SUV. Unlike my mom who had three station wagons, her mom had driven a Pontiac Trans Am, and Bobbi wanted something with style. We were open to new and used, and we were concerned about the price. We had decided Bobbi would be a stay-at-home mom, so we didn’t want to spend too much on a car. We set the budget and started looking.
We first looked at a used Acura TL, but we thought the trunk was too small. We looked at a new VW Passat. I loved the Passat, and we had been pleased with the Jetta, but for some reason, we didn’t buy one. We dodged a bullet there. We looked at the new Ford Taurus. It was at the right price point and it was a nice car. We looked at the top trim, which was fully loaded, but it didn’t speak to us. Bobbi’s uncle, who worked for a dealer group that had Ford/VW/Infiniti/Buick, suggested that if we wanted a big car, we should buy a new Buick LeSabre. He said the LeSabre was extremely reliable and very safe. He was right, and 58-year-old me would have bought one but 33-year-old me was not buying a Buick. We should have listened to Gary. In the end, the car that spoke to us was the Chrysler 300M.

The Chrysler 300M was new for 1999 and built on the heritage of the 300 series letter cars. We knew we didn’t want to pay the price for a new one, but used ones were priced at 20 to 25 percent less –you have to love depreciation. We started our search by going to the local Chrysler dealer, where we met a salesman. I remember his name was Wally, and he was an older man. We told him what we wanted, but he didn’t have any used ones. He did show us some new ones, and we took one for a test drive. We liked it but we weren’t quite ready to buy, as we wanted to make sure everything we needed to take on a trip would fit in the trunk. I went back a couple of days later with all the pack and play, the stroller, the baby bag, and two suitcases to see if it would all fit. Wally wasn’t there but I did load everything into the trunk of a 300M in the showroom. Satisfied, I left a message for Wally to call and that we would move forward ideally with a used one, though open to a new one. We never heard back from him.
I started searching online and I found a white one, but when I went to see it, it wasn’t very clean. In the meantime, Bobbi’s mom had to have surgery in May, so Bobbi went to Pittsburgh to help her parents. Right after she left, I found a silver 2000 300M with black leather interior at Passport Chrysler with only 6,500 miles on it. It was priced right at $24,000. We talked about it, ran some numbers, and decided I’d go look at it. We knew what the payment would be, how much the Jetta was worth, and how much we wanted to put down.
I drove out on a Thursday evening after work, tested the car, and decided it was the one for us. Vince, my salesman, sent me into finance; he had come up with a higher payment that I needed to run by Bobbi. I stood up and said that I would discuss with my wife and get back to him. No one was expecting me to walk out like that. It took just under 40 minutes to get home and Vince had called twice by then.
Bobbi and I decided to put a little more money down but they had to give us a better trade in on the Jetta. In the morning, I called Vince, told him that his price on the 300M was fine but that I wanted more on my trade. I got there by 4PM and we kept going back and forth, so I got up, walked out to my Jetta, got in and started the motor. Vince chased me out and offered $2,950 for the Jetta when I wanted $3,000. I asked him if he was really going to let me leave over $50.00. He asked me to wait and came back, agreeing to the $3,000, and wanted me to take delivery that night. I told him I had a party to go to, which I did, and needed everything done in 45 minutes. Fifty minutes later, I was headed to Annapolis in our new 300M.

Our 300M was the most powerful car I had ever driven. It was quiet, and you could lose track of your speed very quickly. The dashboard reminded me of a jet’s cockpit. It was long and wide with a clock in the center of the dashboard. I opened the sunroof, turned up the stereo, and drove out to the party. When I came home, I parked the car in the center of the garage and just admired it. The next morning, I got up early, mowed the lawn, and then packed an overnight bag. I drove to Pittsburgh to show her the car. Her mom looked at me suspiciously and later asked Bobbi if she knew I was buying a car. Bobbi assured her that we had discussed it and she knew. She and Emily were spending another week with her parents, and I asked if I could drive it home and have it until she came home. She said yes.
Over the summer, the 300M became Bobbi’s daily car. It made trips to the grocery store, the mall, swim lessons, and general errands. It was a big car for just the three of us, but it was so nice to drive. I would drive it on weekends when we went out as a family, but would also keep it on a weekday if I had a work meeting. I had been promoted at work and was now the Internet Sales Manager. Val was a tall guy, as was my AE, so if we had meetings that the three of us went on, I would drive the 300M after switching cars with Bobbi.
The Washington Times had bought United Press International, which had the main office on H Street, NW, by the White House. On Tuesday, September 11, 2001, we had a meeting at UPI, so I took the 300M. In my head, I can see the Potomac as I was getting onto 295. I was listening to NPR, and they had a story about an Afghan warlord who was killed in a suicide bombing. They were finishing the story when the newscaster said an airplane had hit the World Trade Center. I got to the office about 9:05 AM, and the TVs were on. We saw the second plane hit. At that point, we had to leave as we had our meeting. Val got in the front seat, and my AE was in the backseat.
We drove down New York Avenue and then turned onto North Capitol Street. We were listening to WTOP when we saw all this smoke in the distance. The third plane had hit the Pentagon. We turned onto H Street when Val looked over and said, “I don’t want to go. Go back to the office.” I made a U-turn and raced back to our office. There were rumors of a car bombing at the Washington Post, the State Department, everywhere. Everything stopped and people raced home. I waited a little bit and left my office later that afternoon. I was home in 45 minutes where we turned on the news and just watched in disbelief.

There were other times I drove the 300M to work that had much happier memories. I drove friends to holiday lunches, one in particular was at The Four Seasons in Georgetown, where the 300M was parked out front with a couple of diplomatic cars. Other times we went out to dinner, and there were a few memorable vacations: the Outer Banks and Sandbridge, Virginia. Our big souvenir from Sandbridge was Katie, who came home from the hospital in the 300M nine months later. We also made the trip to Pittsburgh for Bobbi’s dad’s funeral. It snowed, and I remember brushing the 300M off before we left for the funeral mass. It was also the car that drove Katie to the hospital so she could have her tonsils removed.

Our 300M was not free from issues. Early on in ownership, we had to have the AC replaced. Fortunately, that was under warranty. We also replaced each door lock switch, the ignition, and the chrome rim on one of the tires. We were in Mexico on a client incentive trip when my dad called and said I owed him $1,500. Apparently, the rim was bent, and the explanation of how it came to be bent was very vague. Needless to say, I paid for the tire and a used rim. I can’t blame the car for the rim. When it had 100,000 miles on it, we decided to do all the required maintenance. We replaced the timing belt, water pump, transmission fluid, and spark plugs. Bobbi loved the car, and we were going to keep it.
Earlier in 2007, I had started working at Roll Call, the newspaper of Capitol Hill. That October, I was at a client lunch, and my cellphone in my suit jacket kept vibrating. Someone was calling me. I would not normally answer the phone, but I took it out of my pocket. I had six missed calls from Karen, and it rang again, so I answered. Bobbi and the girls had been in a car accident. Bobbi was coming home from the grocery store when an SUV slid on a wet road and crossed the center line. Bobbi t-boned him, and the SUV flipped over. They were taken by ambulance to the hospital with minor cuts and bruises. Everyone was fine. They came home that night, but the 300M was totaled. Bobbi insisted I stop by the lot where the car was towed to get our groceries out of the trunk. I couldn’t save much, but I did have the presence of mind to take the garage door opener out of the car. I drove back that Monday and took everything from our car. The adjustor came on Wednesday morning and handed us a check for the car, the groceries, and all the work we had done on the car.
Unexpectedly, we were back in the market for a new car. The new car would be Bobbi’s first new car, and we’d keep it for over 13 years. Next week’s car is what replaced the Infiniti.
Note: Opening photo, not our 300M but ours was silver–courtesy of Curbside Cohort Mlokren2
Related CC reading:
Curbside Classic: 2004 Chrysler 300M – The Dusk Of A New Era
























I remember seeing a lot of these, including one owned by a neighbor. These were impressive cars when they were new. They presented beautifully in a showroom, were extremely roomy and were lovely to drive. Sadly, the tradeoff was the kind of long term durability that Chrysler had been known for in prior decades.
I’d have taken it over the land barge Buick as well. And probably regretted it. The number of 300Ms out on the road seemed to dwindle fairly quickly. But they were lookers and the interior was nicely styled.
The post-merger 300 that came after this was a disgusting cheap plasticky mess in comparison. I remember being absolutely appalled after sitting in one at the auto show.
Oops, meant as an original comment rather than a reply.
You’re right. They were everywhere until one day, they weren’t. I still see Buick LeSabres of that vintage but I can’t remember the last time I saw a 300M. When we bought our 300M, there were 5 others in our neighborhood. By 2010, they were all gone.
When I was writing car reviews, the 300M was one of my favorites for all of the reasons you stated in your story. As JP stated above, Chryslers of this era weren’t known for long-term durability, but it looks like you got one of the better ones.
On another subject, you should do a write up of your mother-in-law’s Trans Am!
The Trans Am is an interesting story. When Bobbi and I started dating, the Trans Am was 13 years old. The t-top leaked, and it had the usual issues you’d expect in a 13-year-old car. My mother-in-law loved the car.
In 2004, I bought the sister car to the 300M, a black over black 2002 Chrysler Concorde Limited…basically the same car, just longer past the rear wheels. I paid $14,990 for it with 35K miles. It was probably the best driving and most comfortable car I ever owned. I must have been lucky, as it only required routine maintenance. I kept it until 2024, when we downsized and I lost my bonus 3-car garage, so it left my “fleet”. It never let me down. I still think it has classic good looks to this day.
I always liked these ‘cab-forward’ Chrysler’s & their sister models. To me they just looked more modern then most other new cars.
I had to smile when I read about you taking stuff to the dealership to make sure all the stuff fit. I am single, but at times had up to five house cats, or three cats and a small dog. My last three new car purchases I also took stuff to the dealership to make sure all would fit. I would only buy two-door coupes, so I required a fold down rear seat with pass-thru to the trunk. Four large cat carriers, litter box pan (empty for testing!), extra space for food & water bowls, soft bag for my stuff, etc., you get the idea. Once loaded had to have room for the pets to roam, once I opened the pet carrier doors my furry family would settle down.
In 2000, I started working in Doha, Qatar, and kept my Texas registered 1996 Sebring LXI coupe in a mid-town Manhattan parking garage as my partner & I had an apartment in lower Manhattan. Not far away was a garage, service station I frequently used & they had my credit card on file for any expenses. My white Sebring coupe was a little obvious, and once my partner drove to the station, popped the hood (amazing he knew how to open the hood) and went to put water where the oil tube was located. Thankfully someone at the station stopped him before damage was done. The station owner contacted me and said if I ever let my partner open the hood again, he was going to padlock it shut.
9/11, think most people of a certain age remembers exactly where were. It was night in Doha, I was answering emails. Got an email from the person who was taking care of my Dallas condo houseplants. Something happened at the World Trade Center. Before I could email a response, frantic banging on my door. A good Afghan friend said something was happening in NYC, come to another flat fast. I arrived at a friends flat just in time to see live on CNN, the second plane hit. I knew from a phone call the night before my partner was in the Towers. So I watched him die live on TV. Within about 20 mins. our residential compound was surrounded by armed Qatari police. A night to remember.
Next day I contacted the US embassy in Qatar. They arranged for our three cats in our NYC apartment to be rescued. The embassy also arranged I was on the second flight out of Doha back to NYC to retrieve my cats. Three NYC cats, two Arab cats, that is why I ended up with five cats flying internationally, or requiring space for multiple cats in my two-door coupes. Later, I remember arriving back in the States, with five yelling cats, I had been in an accident and used a temporary wheel-chair at airports. What and experience traveling with pets. Thankfully my employer sent me and five cats first class.
Something that I have never seen discussed on the Web. All three of my NYC cats were exposed to toxic stuff for a few days as our apartment windows were open. When I went to NYC to retrieve my cats I went to our apartment and it was covered in dust. I just walked away from it as my only concern was getting my cats, getting back to my job in Doha. All three NYC cats later died from cancer.
No insult intended, but for me, “something with style” and that 300M are two things which are mutually excluding each other…in my irrelevant opinion, it’s one of the most ugly vehicles I’ve ever seen. It had some minor success over here in Germany after MB swallowed Chrysler but that faded quickly when many owners found out that even an Opel Omega which had not exactly the rep of being well crafted and reliable fared better than any non-Jeep Chryslers sold here, DC or not.
But, of course, beauty (and practicability) are in the eyes of the beholders and as long as it works, it works.
Friends of mine bought a ‘93 Maxima, but it was totaled by a drunk driver a few months later so they bought a ‘94 Concorde as its replacement. The car had constant niggling problems; the following year they traded it in for a Mazda MPV which they kept for 10 years.
The Gen 1 300M was a great looking car…too bad Chrysler didn’t have the reliability chops back then to upgrade their reputation. If I’m not mistaken the Gen 2 300M was originally to be the Eagle Talon replacement until Eagle got cancelled.
The 300M was unexpectedly well succeeded in Brazil where cars are European – Asiatic standard sized. It really stands out among Passat, Omega, A6 or E320 and due to its oversized proportions it hardly ever fit in a lane row type parking staying near a wheel out the car row. Unfortunately it vanished from the streets a few years later and the following Chryslers were a very rare sight while Hyundai, Kia have been spreading out more and more.
In 98 I found myself selling new Chryslers products for a living. Sold the heck out of those. Just note, I would have called you back.
I’ve always liked these since I saw one at a local motor show. As we’re a RHD country, it was only there as a promo car, and wasn’t intended for sale. I thought it looked great, and quite unlike most other cars out there. When the 300C (which we did get new here in RHD) replaced it, I was disappointed that it turned the 300M’s styling into a dead end. I mean, I liked the 300C too, but the 300M looks much more modern to my eyes. In fact, I think it still looks current today. Who’d have thought that the bold and confident Chrysler that made the 300M (and 300C for that matter) could be such a shell of its former self today…
We had a ’94 Eagle Vision. The 300M was to have been the second generation Eagle Vision before Chrysler killed off the Eagle nameplate.
Really liked the Vision though with time issues showed that Chrysler should have done a better job on engineering. Still it lasted us until fall of 2008.
I started working for Lowe’s in late 1999. They were known for moving store managers around (usually within close proximity to another store.)
Our new store manger was a very highly motivated 23 year old who was making money outside of his job at Lowe’s and bought a brand new 300 in 2000. It was really an impressive car that he would take me to lunch in on occasion. I was driving a 95 Park Avenue that I truly liked better, but the 300 was very sharp.
We owned a 93 Grand Voyager for a bit, but the Chrysler Ultra Drive reared its ugly head and I never bought another Chrysler product.
I really enjoy your series