Been watching this team since the 80's through all it iterations. The MIA deal didn't work out. At the time, it made us Vegas WS favs before it imploded. Hindsight is always 20/20. He has always had balls and taken big swings. He was far from perfect and I dare say he has learned a lot from his time in TOR and elsewhere, like any exec should.
The Tulo Reyes deal was a 2 way dump on bad deals with the Rockies. In terms of aging and bloated deals, its not that much diff than an aging Springer with 3/75 left, and Tulo was integral in the 15/16 runs. After watching for decades in the wasteland, the fan base got re-energized again. We had at that time the longest streak of any MLB team not being in a playoff game.
Aside from Tulo I'm trying to think how many more aging players with bloated long term contracts he left. He also went all in on international money to sign Vlad and left that (which looked a lot more brilliant in '21 than '23 & '24 thus far lol)
Martin was a FA AA signed who gave us a solid front end and 11 WAR on his 5/82 deal - 16M AAV. He was the first big name FA we signed in years, coming off a huge year in PITT. He signed extensions that got the best years of EE and Jose, under market, before they left. The JD trade was a heist.
If Shatkins left today, they leave with us having the oldest line up and rotation in the AL East and our farm is ranked about 20th with Ricky still on it. Not one playoff series win and the window, arguably, is shrinking. (In an era where they have the benefit of MLB adding an extra wildcard- spot). And we will also have the back end legacy of some of our larger longer term FA deals. They have also over seen the renovation of of RC and upgraded our development facilities, and got the payroll up to a level where we can sign some big FA names more often again.
Part of the reason this team even has the big payroll budget it does now to spend on buying a FA rotation is the legacy of the fan interest nation wide being re-kindled with the runs of 15/16 IMO.
Its a mixed bag legacy at this time for both regimes I'd say.