There are 2 things that bugged me about the whole Keano to Liverpool transfer.
1. When it happened, you had many Liverpool fans hailing the signing as Keano was a top striker who could finish the chances that the team was already creating. However, we Spurs fans thought the complete opposite of him. He was a player who was great at creating something out of nothing. He was sneaky, tricky, innovative and could pull something out of the box. He was not someone you would put your house on scoring in a one-on-one situation. In fact, by the end of it, seeing Keano break through for a one-on-one barely got you out of the chair - you knew the end result would be a shot against the keepers shins.
2. At Spurs, Keano had found his level. He wasn't a world beater, but he was better than average. He was certainly one of our better players, the sort of player that stands out at a team battling upper mid-table, but would struggle at a team looking to consistently be in the top 4. Similarly, Liverpool were at about our level or at least on trend to get to our level very soon. He had no reason to want to go to Liverpool except for it being his "boyhood club". That stung. He was a footballing nomad for so long who made his home at WHL. The fact he could leave to join a rival purely out of some emotional attachment to that club damages the years he'd previously spent at ours. When he was leading our troops on to the field at Anfield, was he wishing he was wearing red instead?
I can understand Modric, Bale, Berbatov etc wanting to move because they believe they are "too good" for Spurs. Some players are. It's our job to make sure Spurs gets better so no player is too good for us. But while we still struggle to make the Champions League, there will be players who come and go who have visions beyond our limits. Keane wasn't such a player. It showed at his time at Liverpool and subsequent to that, that his level was Spurs if not lower.