Tito came to Cleveland when they were at their lowest point since revitalizing the franchise in the early 1990s. At that point, they were coming off four consecutive losing seasons, with three of those including 93+ losses. They hadn't had a winning season since they imploded in the 2007 playoffs. Their stars were either leaving (CC Sabathia, Cliff Lee and Victor Martinez had all been traded during their walk year) or breaking down (Grady Sizemore, Travis Hafner) or just didn't turn out to be that good (Faustberto Carmandez). The Dolans were always cheap, but when they did spend a little, it immediately blew up in their faces and crippled the payroll flexibility (Kerry Wood as closer and Pronk's extension). I – and I think most Tribe fans – had a hard time believing one of the game's best managers would choose to come to a small market where ownership couldn't or wouldn't support a perennial winner. He legitimized Cleveland as a place where players wanted to play again for the first time in a decade.
Granted, that first wave of veterans under him was a swing and a miss (Nick Swisher, Michael Bourn, Jason Giambi), but they put up a winning season 9 out of 11 years and never finished with fewer than 80 wins until this year. While the front office might bring in the personnel, I don't think there's been anyone over the past several decades who could manage a clubhouse and build a positive culture on a team better than Tito... even if his exit from Boston was painted otherwise. Cleveland has only had two managers I'd consider good in the nearly 40 years I've followed them (though both were really good), but Mike Hargrove had to put out a lot of fires in the locker room that never seemed to develop under Tito. Hell, Eric Wedge was basically an arsonist himself.