Entitlement suggests that some right or privilege or benefit is inherently deserved. Irrespective of merit. We see entitlement operationalized in our society on two fronts, generally from diametrically opposed stations.
We frequently see those who have positions of power or prestige expect and receive entitlements of some sort as a fringe benefit of their position. Those entitlements might be in the form of club memberships, VIP parking spaces, fatter expense accounts, free tickets to events, deferential treatment, etc. The list gets rather lengthy.
On the other end of the entitlement spectrum are those who claim or expect entitlement due to some disadvantaged or oppressed status (real or imagined). This group of entitlees presume that society owes them something simply because of the hardship they have endured, or are enduring (real or imagined).
The first group does not win my respect. I much prefer folks in positions of power or prestige who are willing to wash the dishes, to help with the babysitting, who prefer to sit with the "common" folks. You wouldn't know them as possessors of power or position by just looking at them. Those are the kinds of people I admire. They seem to understand that they have been richly blessed in life, but are not owed special treatment because of those blessings. In fact, they often seem quite committed to sharing the largess of their blessings with others, both through acts of generosity, and in displays of authentic humility.
As to the other set of entitlement recipients, I have grown to pity them. Regardless of the circumstances that have caused their disadvantaged status, the act of being the beneficiary of "required altruism" from others lessens them in the eyes of those others. Even more, the level of dependence on entitlements from others seems to me to be inversely proportional to the amount of dignity one experiences.
It is through acts of self-sufficiency and self-actualization that we establish ourselves as persons worthy of respect, regardless of our station in life. Both forms of entitlement claimers disqualify themselves (in my eyes) from that respect.
Bottom line: the word "entitlement" carries pretty negative connotations for me (from either vantage point).