On the one hand, the former Everton chief executive watched on as he saw his beloved Castleford comprehensively beaten.
Yet on the other, given he starts work as Super League CEO next week, the 54-year-old Yorkshireman must have been cheered by seeing what this stunning St Helens side are bringing to the competition.
Granted, Castleford, having lost Junior Moors and Benny Roberts to first-half injuries, did rally late on with three successive tries via Jy Hitchcox, Jake Trueman and Oli Holmes.
But they were 34-4 down by the time that flourish arrived in the last quarter having been ruthlessly and routinely dissected by a dominant side that seems destined to take the League Leaders’ Shield off them this term.
Stand-off Jonny Lomax was the star for Saints, showing it is not just Ben Barba who can shine in Justin Holbrook’s thrilling side.
Indeed, Australian full-back Barba limped off in the 55th minute, his own work done, just as it was when he scored a hat-trick here to knock Tigers out of the Challenge Cup less than a fortnight before.
Daryl Powell’s side, having vanquished Leeds Rhinos at Magic Weekend, spoke about making a ‘statement’ against leaders Saints this time around, but the final scoreline told the real story.
Castleford were 22-4 down at half-time and, although they had seen two Greg Minikin ‘tries’ disallowed, were taught some lessons.
They needed to score first in the second period, but instead conceded twice to Saints centre Ryan Morgan, ending the contest.
Roberts returned after missing the last four games, but rather than operating at stand-off or full-back was deployed in the unusual position of centre with Jake Webster injured.
Instead, Michael Shenton was kept at No 1, but Castleford’s main axis, with Jamie Ellis and Jake Trueman at halves, never looked at ease.
Roberts did not complete the first half though, limping off to leave Tigers with second-rows Mike McMeeken and Alex Foster as their makeshift centre pairing.
For Saints, Man of Steel-in-waiting Barba strode around majestically again in the first period.
When Hitchcox kicked the ball long after the half-time hooter it landed perfectly in his grasp.
There was a collective groan from the majority of the crowd inside Wheldon Road, fearing the worst even though the Saints player was 70m away. He does that to people.
However, Barba simply ran the ball over the touchline to close the half; clinical Saints – perhaps for the first time – took it easy.
So often it is the dazzling Australian who creates all the mayhem, but last night it was a true collective effort that saw them take such control.
But also there were too many poor individual mistakes from Castleford; Hitchcox and Shenton both spilled high kicks while the squad’s goalline defence was unusually porous.
The first sign of that came when Kyle Amor muscled over with alarming ease inside the third minute, Danny Richardson kicking the first of his four goals.
In fairness, Powell’s side struck straight back when Liam Watts’s short pass saw Mike McMeeken power over.
However, Ellis missed the simple conversion attempt, an illustration of basic problems that hit them.
It was frustrating; the likes of Jesse Sene-Lefao and Watts made great metres early on and Castleford had genuine purpose.
But too often things went awry when it came to the final third. Twice they forced goalline drop-outs, but neither time profited with a score and some of their final-play options were unconvincing.
They were unfortunate, too, mind; Adam Swift dropped Trueman’s high kick, but it fell to Barba who, in an instant, skipped down the touchline to score from 90m while home fans presumed a knock-on would be awarded
Still, Powell will know both Trueman and Paul McShane should have done better with their tackle attempts before he got into full stride.
They conceded a penalty when in possession to gift position for Saints’ third score, but the superb Lomax had no right to dart between Oli Holmes and Trueman.
When Hitchcox spilled that kick it was England international Lomax who provided the guile with a lovely slipped pass to send Dominique Peyroux over once more untouched.
Their defence was found wanting again, particularly when Lomax weaved through for Morgan’s second.
Theo Fages then crossed and – after that flurry of Castleford tries – he finished it all off, too.
Castleford Tigers: Shenton; Minikin, Foster, Roberts, Hitchcox; Ellis, Trueman; Watts, McShane, Sene-Lefao, Holmes, McMeeken, Milner. Substitutes: Moors, Millington, Massey, Cook.
St Helens: Barba; Swift, Morgan, Percival, Grace; Lomax, Richardson; Amor, Roby, Thompson, Peyroux, Taia, Wilkin. Substitutes: Fages, McCarthy-Scarsbrook, Douglas, Knowles.
Referee: Chris Kendall (Huddersfield).