Sky Sports' Gary Neville favors Arsenal in Wednesday's League Cup final, but the financial calculus tilts differently. Manchester City's domestic cup dominance—five League Cup wins since 2018—translates to recurring revenue streams: broadcast rebates, sponsor activation rights, and merchandise velocity that compound across seasons. Per Matchex data, Manchester United's $6.6B valuation reflects a +10.0% YoY increase driven partly by trophy-adjacent commercial optionality. Arsenal's trophy drought inflates valuation risk despite stronger league position. For City, the League Cup functions as a near-guaranteed cash flow; for Arsenal, it represents a valuation inflection point. City's infrastructure—squad depth, fixture congestion hedging, European distraction mitigation—favors repeat cup wins over single-match performance. The smart money weights history and institutional advantage over pundit sentiment.