For what it is worth here is my take on his signings:
Freddy Ladapo: a disaster, as, for whatever reason, he failed to score in ten appearances for us and was then released. He was picked up by Plymouth, scored eighteen goals for them before being sold on to Rotherham for half a million. Bringing him to Southend was a good piece of work, but, releasing him hints at incompetence as his potential was not spotted. It is easy to wise after the event, but, should it not have been realised he was worth hanging on to?
Sam Barratt: a sad and unlucky tale. He looked like he might be a useful acquisition during the pre season but then went down with a serious knee injury. By the time he was fit enough to play again chaos reigned at the club, and, his confidence needed rebuilding after such a serious injury. MM likes speedy forwards (would he have loved Wayne Gray or not?), and, he was let go at the beginning of this season which I thought was a shame as I love a long throw in. A fair enough signing but an unlucky one. No blame attached to anyone as it just did not work out.
Harry Lennon: on the one hand I can see why he was signed as he has all the attributes of League 1 impact player. The first game I ever watched on I Follow was a pre season friendly against Leeds and he put in a MOM performance, defending stoutly as well as heading home from a corner. Unfortunealy, he has proved to be extraordinarily fragile and quite unable to put together a lengthy string of appearances. Since 2013 he has just played in seventy seven league games and in two and a half seasons with us has only turned out thirty four times. Could his injury proneness have been detected before he signed for us? He cost us a fee, and, I suspect, his wages are not cheap so it can be said this was not CP's best piece of work.
Isaac Hutchison: was he signed by CP? I thought he came to us via Ricky Duncan but I could be wrong. If I am please correct me.
Tim Dieng: is now in the form of his life, and, is slowly winning over the fan base, but, for a while was one the most reviled players on SZ. In 2018/19 he started quite brightly with us, and, despite sometimes being hampered by a calf injury did play forty three times. Last season there were more injuries, and, his form was patchy, but he now seems to be flourishing under the present set up. He can be regarded as a plus signing right now but not many would have agreed with that proposition six months ago. Long may his commanding form continue as I have always liked him.
Sam Mantom: he looked useful when he first came to us, but, somehow his form slowly deteriorated, and, he seemed particularly affected by the chaos that prevailed last under Bond/Waddock/Campbell. Such a sharp drop off in effectiveness could hardly have been predicted, and, by the end of last season he bore no resemblance to the player of two seasons ago. Not a successful signing but I doubt if his drop in form could have been foreseen and these things can happen in football.
Tom Hopper: I was always a fan and thought him a great signing. Unfortunately, he was also the victim of a serious injury after being with us not long. He was out for over a year but by the time he was fit enough to play again the club was already a complete mess and the season irretrievable. We sold him as were in desperate need of funds at the time. He had the potential to be a Southend legend but was cursed by bad luck. Probably CP's best signing, and we did receive a decent fee for him.
Luke Hyam: twenty three games over two seasons. I have no idea of how much he was being paid but I suspect if we were to divide the total money he received from the club by the twenty three games he played he might be right up there as one of the worst signings we ever made. His injury record was not good even before he came to us so perhaps these problems could have been foreseen. In hindsight, a shorter contract might have been a better option but we were stuck with him for two seasons.
Stephen Humphrys: another CP signing who endured injury problems. He looked the goods at the beginning and later scored 'the goal' vs Sunderland but despite his obvious ability was not fulfilling his potential by the time he moved on to Rochdale at beginning of this season. Had CP managed to keep his job, or, had we found someone half competent to replace him would things have turned out differently? After what he had to endure under the enigmatic Sol Campbell it was entirely logical he would want to leave Southend. By no means a bad signing but the fates conspired against him having the career he might have had with us.
Of the loanees Shayon Harrison and Mc Coulsky had a limited impact with, and, as I remember, Stockdale was an emergency loan who played just three times for us. Harry Bunn put in a shift from time to time although he was yet another CP signing who spent a lot of time on the treatment table. Taylor Moore might be struggling to establish himself in a top Championship side but I thought was an effective League 1 player. A very good long term loan signing. And Sam Hart we know well. He is wholehearted and more than useful in League 2, and, I have no doubt he can hold his own in League 1.
Yes, CP had bad luck with injuries with some players but both Lennon and Hyam were known as being fragile even before coming to Southend. They can only be seen as terrible signings while Ladapo perhaps should never have been released. I am willing to give him the benefit of doubt in respect of Humphrys, Mantom and Barratt.
Hopper was super signing while Taylor Moore was a good one.
Dieng and Hart are still with us, and in the future hopefully they can both play for us long enough for me to reappraise CP's record.
At of now I would submit that overall his record is mixed only.