When the next-generation Porsche Cayman arrives in roughly a year’s time, it and the new Boxster will both be fully electric vehicles. You read that right: Internal-combustion engines will no longer power Porsche’s mid-engine sports cars. That makes it a great time to look back at the now-affordable first-generation Cayman, a car that was aptly named after a particularly small and agile breed of crocodile.

The middle child

When the 2006 Cayman S launched in late 2005, Porsche claimed it was an all-new model situated between the convertible Boxster and the flagship 911 in the brand’s sports-car hierarchy. In truth, the curvy 2-seater was based on the Boxster’s underpinnings. Styling changes made for a unique coupe, with voluptuous rear fenders, unique front and rear bumpers, a large rear cargo hatch and other tweaks. Porsche cited the 1953 550 Le Mans coupe and 904 GTS race cars as design inspirations.

While coupes are typically less expensive than their convertible siblings, Porsche flipped the script: A 2006 Cayman S started around $60k, nearly $5k more than the Boxster S. As justification, the M97 3.4-liter flat-6 produced 295 horsepower in the Cayman S, 15 more than in the Boxster S. The solid roof increased chassis stiffness by 150%, allowing sharper suspension tuning. It made the Cayman a purist’s sports car, appealing not only to those who found the Boxster too cute and the 911 too expensive, but also to those who felt the 911 was simply becoming bloated.

The base Cayman followed in 2007, with a sub-$50k base MSRP. Its 2.7-liter flat-6 made 245 hp but was saddled with a 5-speed manual gearbox rather than the 6-speed of the Cayman S. (A Tiptronic automatic was available on both.) Apart from badging, base models can be identified by a single oval exhaust tip, smaller brakes and 17-inch wheels. The 2006–08 Caymans are referred to as 987.1 models.

An evolved 987.2

In 2009, the 987.2 Cayman arrived with minor cosmetic updates but a major powertrain revision. The new 9A1 flat-6 ditched the intermediate shaft (IMS) and its troublesome bearing, and had an improved oiling system that was particularly appreciated by those owners who pressed their cars into track duty. This was also the Cayman’s introduction to the new Porsche Doppelkupplung (PDK) automatic, which replaced the torque-converter Tiptronic and accounted for the majority of 987.2 sales.

The base Cayman engine now made 265 hp from 2.9 liters, and the car got the S model’s 6-speed gearbox and larger brakes. The Cayman S received a direct-injected 3.4-liter with a bump in output to 320 hp. Crucially, a limited-slip differential was finally available on all Caymans.

It’s worth noting that a low-production Cayman R model arrived at the end of 2010 with 330 hp, 100 pounds in weight savings, standard LSD and a more-aggressive aero package. These are above our “affordable” price window; average Cayman Rs start around $55k and shoot upwards of $80k for investment-grade examples.

Eye before you buy

Notorious IMS-bearing concerns loom large in this era, but 987.1 Caymans have a more-robust bearing than those found on preceding 986- and 996-series models. While failures can still occur, the odds are lower — and again, 987.2 Caymans solved the problem by having no IMS bearing at all.

Bore scoring is another serious issue, but only in 3.4-liter S models; 2.7- and 2.9-liter base models are immune. Browse the popular Porsche forums and you’ll find various underlying causes, but the end result is the same: damaged cylinder walls, increased oil consumption and lowered compression. Bore scoring is more prevalent in 987.1 cars, but occurrences in 987.2 cars are becoming more frequent as they age. Aftermarket rebuilders claim to have solutions, but a turn-key replacement engine can run upwards of $25k. A pre-purchase inspection by a Porsche specialist that includes borescoping each cylinder is essential on any Cayman S. Metal bits from both scoring and IMS failure will show in the engine oil.

Further, while PDK gearboxes are relatively reliable, if trouble strikes, repair options are limited. Porsche generally defaults to a complete replacement, at around $20k. Regular PDK service is also somewhat pricier than with manual gearboxes. If reliability and low operating cost are paramount, seek out a 987.2 base model with a manual transmission.

Crocodile hunting

Prices for higher-mileage 987.1 cars start under $20k, with excellent examples moving into the low-$30k range. Because 987.1 S models are seen as the least reliable variant, the price gap to base cars is often smaller. It’s not uncommon to see 987.1 S models with replacement engines; rebuilt in a preventative manner; these can be less troublesome.

The Great Recession meant relatively few 987.2 Caymans were produced between 2009 and 2012. Rarity and increased reliability equate to higher prices, so $25k is a good starting point for a base 987.2 with higher miles, while babied condition-2 cars hover around $35k. Add about 20% for a 987.2 S. PDK transmissions were the volume seller, so manuals are rarer and worth a small premium. Options such as a limited-slip differential, full leather interior, sport exhaust and unique colors also add value.

Whichever 987 Cayman you choose, you’ll have a car that is direct and engaging, the last of its ilk to feature hydraulic-assist steering and a traditional handbrake before both went electric. Porsche has already accepted these cars into its Porsche Classic program, and good examples will doubtless become harder to find as the years and miles add up. With proper due diligence before purchasing, a 987 Cayman can be a rewarding and highly usable sports car from the cusp of Porsche’s analog era. ♥

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