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I really like the looks of the older bikes. I want a chief, but what's better motor wise? As far as power, sound, reliability? I'm a fairly new rider and always dreamed of having one of these bikes. Just want to get it right the first time. Thanks
 

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Gilroys started out with S&S engines then went to their proprietary Powerplus motor towards the end. Kings Mountain Indians were essentially the same bikes right up through 2013. Polaris continued to make them after they bought out Kings Mountain in 2011. 2014 and later were Polaris designed and manufactured.
 

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2012 Indian Chief Vintage . 2016 Indian Roadmaster
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Gilroy (called as such due to it's location in Gilroy,CA) used S&S 1999-2001 in the Chief. They continued to use the S&S in the Scout until 2003. A motor called the Power Plus, or nick named the Bottlecap were used from 2002-2004 in the Chief. The company went bankrupt for a number of reasons mainly the approximately 70% failure rate of the Power Plus engine. I personally had my engine in my 2002 Chief rebuilt 3 times until it was right. I additionally think that although they failed miserably in the engine department they made an extremely ascetically pleasing bike. I believe the 2003 Indian Chief Vintage is one of the most beautiful Indian Motorcycles of all time (red of course). A British Investment Company called Stellican that bought brand names and makes investment and then sells them began to manufacture the Indian Motorcycle at Kings Mountain, NC in 2009 they maintained ownership until 2011 when Polaris acquired the brand. The first Polaris bike was manufactured in October of 2011. I am quite certain of this date as I bought the first Polaris made Indian for sale Serial Number 00000002. The 00000001 bike is in Spirit Lake I am told.
642534

2003 Indian Chief Vintage
 

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As far as power and sound they are relatively close and easily changed with timing, exhaust, etc.
Reliability changes though. The Gilroy engines and bikes went through a lot of changes. I think your better off with a later model S&S (The S&S ran from 1999-2002, so a 2001 or 2002 had some of the bugs worked out) and the PP 100 was hugely problematic and least reliable, as Micmac mentions.
For reliability look towards a Kings Mountain bike (2009 - 2011) and their PP105.
They are all older bikes with flaws, and it’s good to investigate and understand the general market for them. But a lot comes down to the individual bike. Mileage, maintenance, repairs, upgrades, and so forth.
If you like them it’s definitely worth the time and effort to hunt down and enjoy a good one.
 

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I'm not trying to hijack the thread, but I see a lot of those fat tire choppers from like 15yrs ago for sale pretty cheap. (Big Dog etc...) I never liked those things but they usually came with a big ole carbureted S+S engine. Does anyone know if one of those engines would fit in a Gilroy Scout?
 

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Yes they would.
 

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Good to know. (y) Thank you good sir. Every time that I see one of those "Chopper" things for sale I think..."Hmmmm... I'd like that engine, tranny, primary, and brakes. I dunno what I'd do with the rest of it. " It's a shame. Those things were expensive and flashy when they were new and nobody wants them now.
 

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You'd be surprised on how many think they compliment off their "Son's of Anarchy" t-shirt wardrobe.

Anything you ever wanted to know about Gilroy Indians. This was our go to resource. Very extensive archives. We had each other when there was no dealership or factory anymore.
 

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You can also find all the downloads for the manuals on Homer's page at the forum mentioned above or just go to granbygarage. All the information is there as well.

If you can find a powerplus that has been rebuilt correctly it is likely the collector item for that era as the engine was proprietary as was the frame, swingarm, tanks, sheetmetal, etc. etc.

For ease of finding parts and maintenance then the S&S motor is a better choice. Specifically, in those Chiefs you are best to have a 2001 as by then all the bugs had been worked out in that style Chief.
 

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Here are my two Gilroy bikes. I wish I still had them. I still wonder to this day why I ever got rid of them and it is one of my few regrets in life. The top is a 2002 Indian Chief Roadmaster with the aforementioned self grenading Powerplus, the bottom is my 2002 Indian Scout. Never had a lick of a problem with that bike. There were several guys got over 50K miles with their stock Powerplus, but they were the exception, rather than the rule. My first engine went at 7 thousand miles, the second about the same. I bought the second one off eBay from a guy in Michigan Bill Melvin who had purchased most of the leftover stock from the Gilroy plant closing. I had it rebuilt by a reputable and 30 thousand (I'm guessing because I also had to replace the speedo three times because they had a propensity to develop their own micro climate and self destruct. Autometer rebuilt them (speedo's) for a time free but eventually quit). I have often said owning that bike was like being in love with a lady who had a fondness for crack cocaine. What could have been. The Indian Motorcycle mantra.......
 
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