Pitching Coach. Salary: $500,000 

Having had a decent fifteen-year career in the majors, you've made the transition into coaching. Since you were a dominant pitcher, it makes sense that the team makes you their pitching coach. What makes less sense are the pink and orange uniforms—but it's not like they hired you for fashion advice.

First-Time Head Coach. Salary: $750,000 

You've finally gotten your own head coaching job. After the team's last manager led them to an unspectacular eighty-loss season, they're looking for some new blood to help rejuvenate a storied but struggling franchise. As you're introduced to the team, you stand and accidentally hit your head on a low-hanging beam in the clubhouse. Apparently you took the "new blood" thing literally.

Experienced Baseball Manager. Salary: $1,000,000 

Noticing the rookie infielder is having trouble connecting with the ball when he's batting, you sit him down to go over some of the fundamentals of being in the big leagues. He listens patiently as you go over your history. When you finish, you ask him what he learned. He says, "I should've asked for another million." Kids.

Successful Skipper. Salary: $3,000,000 

After a tough loss, you head to the press room to do your normal post-game press conference. When you get there, you find out news just broke about your superstar first baseman getting arrested. Well, at least no one's going to ask about your boneheaded decision to leave the starting pitcher in there in the eighth inning tonight.

Legendary Manager. Salary: $5,000,000 

As you polish the three rings you have from your World Series wins, you reflect on a life spent coaching in the big leagues. You look at all the trophies and other awards sitting in your coaching case. Your smile fades only a little when you look at the almost-empty player case. Oh well—that's why people get second chances. Now go take a dip in your massive pool, you rich champion, you.