I have only seen Sean De Silva play a few times. First time I did hear about he was in a U 15 tournament a couple years back and the reports were the usual from a "touches" player.
"A lil white boy come on and start to heat up de place" "De small man show some wicked touches and ting"
From the reports, I gathered that crowds wherever he played loved him. The descriptions of him were always the same..."small, little, touches, could play".
Then I actually saw him and he was as I expected. Technically sound, good passer, two footed, pleasing to the eye to watch. But his deficiencies in a midfield role were also obvious. Small, not that strong on the ball, not that fast, not a tackler, not stong in the air.
So the issue for any coach is....how does this player fit into my scheme?
T&T basically plays a 4-4-2 system. Sean isn't a striker. He isn't mobile enough or strong enough to play the position and he's not a natural goalscorer. He won't be playing defence so the only place for him is midfield.
In midfield, if you put him wide, one of his roles will be tracking back and containing the opposition wide player. That is not one of his strengths. The only position therefore for him, is in a central midfield role. Now in days gone by, you used to have this "midfield general" role which has all but disappeared in today's game. That player now has a different skill set. That player is one who runs at the defence, can make the killer pass, is strong on the ball, and creates space for teammates by their presence. They typically in today's game play just behind the strikers. That however, puts extra work on the other midfielders because they now have to cover for the playmaker who typically isn't one that tracks back too often (see Riquelme, Zidane etc). You have to have the players who can cover the midfield to play that system....or play 1 striker less.
Latapy can play that position. Hleb can play that position. Rooney can play that position etc. Given T&T's system and team composition, I'm not sure the coaches could afford to play Sean from the start. Maybe he could....I wasn't with the team so I can't say but based on what I have seen of him...that would be my wild guess as to why he doesn't start.
He reminds me of another ole CIC player....Kevin Moze. Pretty pretty player. Used to call him Hoddle. Was on National youth teams a few times but never made the step up. Pity....because he had the "touches" too. His brother Gavin was less technical but much more of a battler and arguably more effective as a midfielder at the higher level.