www.iFourWinns.com

I have four winns branded two axle trailer for my boat. I am unable to get any grease into one of the nipples using grease gun. I am able to lube 3 out of 4 just fine but for one, after I start pumping, the new grease starts coming out right at the grease gun fitting instead of old grease being pushed out of the bearings. I tried to push back onto the small hole on the nipple, using a needle and it moves in just fine. Doesn't appear to be stuck. I am not sure if I just need a better grease gun or if something has gone wrong with the bearing. I am using this grease gun: http://www.amazon.com/Lincoln-Lubrication-1134-Pistol-Grease/dp/B0002NYDZ8/ref=sr_1_2?ie=UTF8&qid=1401211691&sr=8-2&keywords=grease+gun Maybe a stronger fitting that grabs onto the nipple tighter might work?

Are you sure that it is a grease zerk or a breather valve of some type instead? Both look similar, at least mine do.... Do you also have turbo lube hubs? Just curious

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2008 H220 Frenzy - 5.7L VP SX Drive
2013 Tahoe LTZ Tow Vehicle (admiral's ride)
2011 Ford F150 XLT Ecoboost Tow Vehicle

Honestly I am not 100% sure of anything because this is the first time I tried this. I didn't worry about this too much in past because I haven't used it much except once a season to take the boat to the marina and bring it back at the end. I also have a triton trailer with sure lube and the setup looks the same on my four winns. It has a rubber cap similar to this:
When you remove rubber cap, you see something like this:

On the other 3 wheels, it worked like this:

The last wheel, clear grease started coming out right away, but then I noticed that it was being pushed out of the sides of the fitting on the grease gun. On other 3, I definitely saw different color grease coming out for many pumps until it turned blue, the color of the grease I was using.

Also, my trailer looks identical to the trailer in the picture in your signature except for that it's red.

From my research it appears, I either need one of these: http://www.amazon.com/LockNLube-Grease-Gun-Coupler-Lock-/dp/B00H7LPKKU/ref=sr_1_5?ie=UTF8&qid=1401225441&sr=8-5&keywords=zerk+fitting or a new nipple fitting. Anybody knows if it's possible that it may be something worse?

Can you unscrew the grease zerk and use a piece wire or clothes hanger and push it into the hole. The grease may have hardened and is stopping it from going in. If that doesn't work you may have to remove the hub and probe the hole from the other direction.

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'96 200 Horizon 5.8l VP/SX

I just wanted to update everyone on what ended up working for me. I just bought a better grease gun fitting and it ended up working... well it worked until I ran out of grease. It was some heavy dutty fitting from napa for less than $5. If you have the grease gun mentioned above, you may want to try a better fitting if anybody happens to have the same issue.