Jed has spent money and payroll. His job is to literally maximize the WAR per million spent. The issue isn't avoiding terrible mega contracts to get stars, its that he's been really inconsistent at value-spending in FA, while also not having a ton of surplus from young players.
Jed has done well with with his 3+ year acquisitions like Imanaga, Seiya, Taillon. He extended Happ and Nico. But he hasn't done the same care with value with low-end talent like Smyly, Mancini, Barnhart, Hendricks, Neris etc. The Billy Beane's A's or the Rays never went out and spend 9.5m AAV on Smyly or 7.5m on Mancini or 6 million on a washed up Arrieta etc, all guys with borderline replacement talent/tools.