Simon Dedalus is the father of Stephen Dedalus, the young protagonist in both, and his character is largely based on Joyce's own father, John Stanislaus Joyce. Simon is a passionate Irish nationalist and supporter of Charles Stewart Parnell, facilitating his financial success within Dublin society in Stephens' earlier years.
To add to the financial nightmares of the Daedalus family, the father had a particular aversion to paying rent for their lodgings. It was the family’s custom to stay in one dwelling as long as Simon could wheedle the landlord into letting them stay; then it was off on the increasingly familiar ritual of moving to new quarters. These events follow an almost straight path from good apartments to bad.
Simon Daedalus was never troubled for long by the need to move, for he could always rejoice in his canny ability to find new quarters without paying tor the previous ones. It should be stated in defense of Daedalus, that he fully expected his oldest son to manage the household affairs, and at least contribute something to the family treasury.
Stephen remembers "his father's gibes at the Bantry gang," which suggests an earlier allusion by Simon Dedalus to Ireland's current political state, comparing it unfavorably with the parliament of “Hely Hutchinson and Flood and Henry Grattan and Charles Kendal Busche.” In other words, Simon gets the feeling that nowadays, Ireland is incapable of producing anything, but degenerates such as the "shriveled manikin" on the library steps.
One of the unfortunate consequences of Simon Daedalus' irresponsible nature was that the family was often in financial difficulty. And as the publican progressed further downhill after Parnell's demise, these difficulties became more frequent. Daedalus seems to know all the "right people" in Dublin, but it appears that they know him too well to trust him with any major responsibilities. Being a proud man, he will not settle for any job beneath his station, and so fabricates a vision of himself as persecuted by those in power.
Mr. Simon Dedalus in the Essays