Holding Tefillin during Prayer
“One should not hold Tefillin in his hand while praying the Shemoneh Esrei; nor should he hold Holy Scrolls, a plate or the like with contents; nor a knife, bread or money, since in all of these cases the holder will be worried that he might drop the object, thereby causing one's concentration to be disturbed.” (Shulchan Aruch Orach Chaim 96:1)
Even if one does hold one of the above-mentioned items, he does not need to pray the Shemoneh Esrei again unless he is certain that it is the reason he did not have proper kavanah (understanding the meaning of the words) for the first blessing of the Shemoneh Esrei. (Mishneh Berurah)
The above comments of the Mishneh Berurah require clarification. To what type of person does the above ruling apply? If it is someone who generally has difficulty with proper kavana (intention for what he says), how can he be sure that his lack of kavana this time was because he was holding onto one of the above items? Perhaps he would have had the same problem even if not holding the item.
Accordingly, it would seem that the Mishneh Berurah is referring to a person who doesn't normally have difficulty with kavana when praying the Shemoneh Esrei. Since he always (or almost always) prays, at least the first blessing, with kavana, he can be certain that the reason for his lack of kavana this time was a result of his holding the item in his hand.
The above analysis brings us to another difficulty. In Shulchan Aruch Orach Chaim 101:1 the Rema writes, based on the Tur, that today we do not repeat the recital of the Shemoneh Esrei for lack of kavana during the first blessing, since it is likely that the lack of kavana will happen yet again.
What type of person is the Rema referring to? If he is referring to all people (both those that have difficulty with kavana and those that don't have difficulty, then how can the case of the Mishneh Berurah ever come up? In any instance the worshiper would not repeat the Shemoneh Esrei, since nowadays we do not pray again. From the above it seems that according to the Mishneh Berurah the words of the Rema apply only to one who has difficulty with kavana, for only in such a case will it be likely that it will happen again. This is why the Mishneh Berurah rules that one who is certain that his lack of kavana in the first blessing was solely because of the object in his hand must pray again.