That Drag specialties battery will start that bike no matter how cold it is. I sold batteries for years and the CCA280 means it is capable of cranking 280 CI for 1 minute.
If you where using a Battery Tender your 4 year old battery wouldn't be dead. I got 7 years out of my first Sportser battery and my wifes bike is 5 years old and hers still works perfect.
One of the secrets of using a Battery Tender is it will keep the battery charged to capacity and also keeps it warm and a warm battery will have a lot more cranking power that a cold battery. I had times that a car wouldn't start and all I did was take the battery in the house let it get warmed up and it would start the car, the same trick works on bikes.

 

Huh?


CCA (cold cranking amps) is a measurement of the starting power of a battery at 0°F under a load (ampere draw) for 30 seconds with the end voltage maintained at 1.20 volts per cell. Several variations of CCA ratings may be applied to a battery including; MCA (marine cranking amps) or CA (Cranking amps), which are generally 20% higher than CCA (cold cranking amps) and reflect higher temperature testing.

 

Get a new battery from HD and a battery tender.