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Why would a trainer enter a horse knowing that the weight that he will be required to carry has appeared to be a problem in the past? The obvious answer is that he knows that weight wasn't the problem. Perhaps his horse hadn't been training as well then as he is now, was tactically disadvantaged in the race, or had traffic problems. Another answer is that the horse isn't in today's race to win, but rather for conditioning purposes. Take a look at the race that followed the poor ones that bother us. If he ran big after dropping three or more pounds his next time out it is quite possible that the poor race with the added weight was simply a conditioner designed to get him ready for the big effort that followed.
Particularly at races of a mile or more 'weight shifts' are very important in handicapping. Let's assume that we like horse A's chances in a particular race. He's adding four pounds today but has run well with that weight in the past so we normally wouldn't be concerned. Horse B, however, is dropping four pounds so the actual advantage he is gaining is eight pounds. Eight pounds won't make a winner out of an unfit or outclassed horse but, it can spell the difference if B qualifies as a contender in all other respects. The four pounds added won't stop us from backing horse A, but the eight pound 'weight shift would sure cause us to think twice.
Some horses race with more than their assigned weight. Such overweights are usually announced while the horses are still in the paddock. Most are caused by the jockey being unable to make the weight. One or two pounds won't bother the horse much so the can generally be ignored unless the jockey has been in a slump lately. Our concern should instead be focused on the jockey. Maybe he hasn't been winning much lately because he's weak and dehydrated from almost starving himself. Female riders may not be as strong as their male counterparts but they have a big advantage when it comes to making the weight.
Our ears should perk up whenever it is announced that a capable trainer is waiving the apprentice weight allowance that he is entitled to and switching from an apprentice to a veteran jockey. It doesn't mean much is the change is to a fellow who doesn't win very often, but if he is switching to a top rider it is usually a clear indication that he is out to win. He knows how well his horse has been training, who his horse will be running against, how the track has been playing unless its an early race, the post position, and has decided that his horse has a big shot to win. The top jockey's agent probably agrees.