2019 Jeep Grand Cherokee vs 2019 Toyota Highlander
Two midsize SUVs, compared on what actually matters when you're buying used:
what breaks, when it breaks, and what it costs you.
2019 Jeep
Grand Cherokee
6/10
Buy the 3.6L Pentastar Limited or Overland, skip the diesel and the base electronics gremlins, and it'll be a genuinely nice place to sit for 150k miles.
VS
2019 Toyota
Highlander
7/10
Buy it for the third row and the TNGA-K bones, not for driving joy — and get the transmission checked before you sign anything.
Milo scores the 2019 Toyota Highlander higher — 7/10 against 6/10.
By the numbers
Green is the better number — higher on every score, lower on failures, complaints and recalls.
| Jeep Grand Cherokee |
Toyota Highlander |
| Known failure points | 8 | 6 |
| NHTSA complaints | 358 | 472 |
| Safety recalls | 7 | 3 |
| Service bulletins | 12 | 12 |
| Reliability | 58 | 74 |
| Cheap to own | 52 | 68 |
| Fun factor | 61 | 38 |
| Holds value | 55 | 78 |
| Enthusiast cred | 48 | 22 |
The most expensive thing that goes wrong
2019 Jeep Grand Cherokee
ZF8 8-speed transmission harsh shifting/shudder from worn valve body or degraded fluid
$400–$4,00060k–100k mi
2019 Toyota Highlander
UA80 8-speed automatic transmission whining/shuddering, sometimes progressing to hard failure on V6 models
$4,000–$6,50060k–100k mi
If you buy one, buy this one
✅ 2019 Jeep Grand Cherokee
A 2019 Grand Cherokee Limited or Overland with the 3.6L Pentastar V6, non-air suspension (standard steel springs), and full service records showing the diesel/brake recalls aren't relevant — or if you want performance, a well-documented SRT with the 6.4L HEMI and Brembo brakes.
✅ 2019 Toyota Highlander
2019 Highlander Hybrid Limited AWD — same TNGA-K platform, better real-world mpg (~30 combined), and it sidesteps the UA80 transmission risk entirely.
Narrowed it down? Get the full report
This comparison is model-level.
Milo's report goes car-level — the one you're actually looking at:
- A line-by-line negotiation script
- The pre-purchase inspection checklist
- VIN-specific open recalls
- What it's really worth right now
- Your next 15,000 miles, forecast
- Hidden features & money-savers
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Scores and findings blend documented NHTSA recalls and complaints with
patterns synthesized from owner communities. Always inspect the specific vehicle and
verify open recalls by VIN before buying.