Yeah, more short-sighted or "penny wise, dollar foolish" than anything. History has shown he's willing to increase the payroll after more money starts rolling in thanks to increased attendance after a winning season. But, he always stops just short of really putting this franchise over the top. Their big "All In" move (which became their advertising slogan that year) that I can think of was to sign the one-dimensional, 32-year old Adam Dunn to a four-year contract. Even with the infamous Hahn rebuild where "the money will be spent", he wouldn't commit to Machado or Harper and instead the Sox spread all that payroll space they had on B-level free agents like Keuchel and Grandal plus trying to outsmart the market by signing their young, unproven talent to extensions. Not to mention that this has taken place on top of not investing enough in scouting, player development, international scouting, etc. Look at the Padres. Yeah, they have no WS titles or pennants to show for their actions, but they now draw 3M a year and were sold for nearly $4B thanks to fielding exciting teams and developing a top-notch ballpark.