I’m a guest on Tuesday’s edition of Effectively Wild, the daily podcast from Baseball Prospectus. It was a thrill for me, as one who has listened to all 430-plus episodes of the podcast thus far. Co-hosts Ben Lindbergh and Sam Miller graciously carried me through, because I’m rather out of practice when it comes to interviewing or broadcast of any kind, so please give the whole thing a listen. The episode’s conceit was a contest, conducted by me, between Ben and Sam, to see who could guess closer to the actual career earnings of several players.

There were 11 guys in the quiz, and while many of the pertinent things that led me to choose each of them drew mention during the podcast, I have a few spare notes about each that I wanted to share with you:

Steve Avery: One of the last very good players who, despite a fairly full career, left the game not necessarily set for life. Ben and Sam each underestimated him: He did make $21,625,000 during a career that spanned from 1990-2003.

Avery’s total earnings are one interesting thing about him. If you stop and think, that’s right on the line between being set for life, and your kids’ lives, and not. Avery turned 44 Monday. He lived, for about a decade, the very expensive life of an MLB ball player, maintaining multiple residences, tipping clubhouse workers, making charitable donations, (hopefully) paying someone to manage his money, the whole thing. I’ll consider myself very lucky if I make $3 million during my lifetime, but I don’t have any of those expenses for which to account.

I know it sounds strange, but a ballplayer who makes $20 million probably will have to work in some other capacity during their life. Now, teams offer a wide range of golden-parachute options, from coaching to broadcasting to scouting, and there are public-appearance opportunities (although the memorabilia market is in freefall) and chances to open car dealerships over which you need have no actual control in order to make money. Still, there’s a distinction to be drawn, because guys who fall in about Avery’s range of income are easier to empathize with, easier to see as human, for just this reason.

In Avery’s case, that goes even a little bit further, because there’s an element of bad timing, of historical misfortune, to his story. Avery had a rough but encouraging rookie season in 1990, at age 20, and then was a true phenom for three more years. Before the third of those, in 1993, his team, the Atlanta Braves, signed Greg Maddux for more money than any pitcher had ever been paid. Maddux completed a triumvirate, with Tom Glavine and John Smoltz, of young and dominant pitchers who were locked up on long-term contracts. As Avery told Sports Illustrated in 1993, though, “I’m the one who’s really locked up. If those guys are locked up, they don’t mind being in jail.”

He was referring to the fact that he wasn’t yet able to start earning the big bucks that were rolling in for his more veteran colleagues. As it turned out, he’d never get there. In September 1993, after a season in which he was, quietly, an absolute star and the most consistent Braves starter, he left a start early with an injury to an arm or shoulder muscle near his armpit. He was never the same guy. He managed a few more roughly average, if injury-mottled, seasons, then all but washed out of the league.

In fact, from 2000-2002, he didn’t throw a single pitch in the Major Leagues. He might never have gotten back, were it not for the 2003 Tigers. Avery is a Dearborn, Mich. native, and had kept striving to get back to MLB, even after falling completely out of affiliated ball for two years. He made 19 appearances for Detroit that season, hanging on the roster for a couple months. I can’t prove this next part, but it seems to me to be true: Avery reached 10 years of MLB service time, qualifying him for the MLB lifetime pension, during that 2003 stint. Avery came up in mid-1990, and accrued full seasons of service time from 1991-99. He should only have needed a couple months’ time in the Show to get over the top, and he pitched from May 11 through July 20 that year.

I don’t tell you this cynically. There’s something admirable about it, both on the part of Avery and on the part of the team. The Tigers were atrocious that season; it was no secret. They did a very large favor for Avery without hurting much of anyone, and Avery did his part by continuing to look for routes back into baseball years after others might have given up. Again, if Avery had made even $30 million during his career, my perspective might be different, but he was just human enough, just normal enough in terms of earnings, that the story of his comeback can be touching and uplifting, even if it was, on some level, about money. Anyway, Avery is very interesting to me, and from the moment I heard from Sam, his was a name I knew I would want to include.

Dontrelle Willis: I used Willis as a contrast point with Avery. Willis has made over $40 million in his career to date, essentially following the same career path that Avery did, 10 years later. Willis is back in MLB, now, which is great for him, but I never ached for Dontrelle Willis the way I would have for Avery. Even adjusting for inflation, Willis made 70-80 percent more than Avery. He’s still an interesting player, but Avery’s career has more texture. The point is that, though the people who vilify players or begrudge them their success are fools, the money players hsve come to earn over the last decade and a half does create a sense of separation between us and them.

Bob Horner: One of the rare breed of player who needed (or at least was perceived to need) no minor-league seasoning, Horner debuted the same year (1978) that he was drafted first overall. Between going straight from college to the big leagues and hitting four homers in a single game, Horner gave himself a lot to which to live up, and he never really did it.

He was a star, a borderline superstar even, in his youngest days. He hit 91 home runs from 1978-80, and that was despite injuries that limited him to 1,369 plate appearances—basically, two seasons of playing time. Injuries became far too prominent a part of the story of his career, though, and he not only failed to stay in the lineup, but became an atrocious defensive third baseman as he entered his late 20s.

Still, at the end of the 1986 campaign, he owned a career slugging percentage north of .500, had clubbed 27 homers in consecutive seasons and even set a career high with 141 games played in 1986. The aforementioned four-homer game came in July of that year. He was 29 years old, and still had a chance to be one of the best power hitters of his era. Oddly, then, no one wanted to sign him for the 1987 season. I do mean no one. The owners colluded against the players that winter, driving down the cost of players so much that Andre Dawson went to the Chicago Cubs by offering to play for whatever they would pay and Tim Raines lost the first month of the season before being allowed to re-sign with Montreal.

Horner, somewhat too proud to try the Dawson gambit and less talented than either of those guys, was frozen out of the league altogether. He went to play in Japan, came back to MLB in 1988, injured his shoulder and never played again. We have no sound basis to believe that Horner would have miraculously avoided injury if he had not been forced out of baseball during the typical late peak years, but it sure feels like this was a great player stolen from fans, at least in part, by the greed of owners. He made $6.8 million in his career.

John Olerud: Like Horner, Olerud went straight from college to MLB. Olerud was a more complete package, though, a more well-rounded batter, a much smoother fielder (although at a less valuable defensive position) and such a gifted athlete that Toronto let him try pitching in the fall instructional league, even after he’d debuted as a batter in September.

Olerud played from 1989-2005, about the perfect years at which to peg the explosion of salaries across the game into the stratosphere. He lost only the same partial season that everyone else lost to the greed of owners, in 1994, and made over $68 million.

Alex Sanchez: The first player ever suspended under MLB’s testing system for performance-enhancing drugs, Sanchez was a .296 hitter over his short career. He also stole 122 bases, although he was caught so often as to be a net negative as a runner. He didn’t have much power, which made his case a nice refutation to those who claimed that PED use alone could even begin to explain the league-wide power surge from the mid-1990s through the mid-2000s.

He also didn’t make much money, just $1,243,000 over parts of five seasons. He played for both the 2002 Milwaukee Brewers and the 2003 Detroit Tigers. His teams were more than 100 games under .500 when he started, and he only played 427 career games. It might well be that PED use only put the final nail in the coffin of a player whom the league already viewed, fairly or not, as a loser.

Raul Ibanez: As Sam has been fond of pointing out in the past, Ibanez has essentially had the career of an average Hall of Famer since turning 30. It’s just that he wasn’t much of a player at all until then. I chose him as a way to check in on the effect of having success later in one’s career than most do, and sure enough, Ibanez—whose second-most comparable player (per PECOTA), Matt Stairs, made just under $20 million in an average-shaped, almost perfectly contemporary career—has pulled down over $66 million.

It pays to break out once you’re able to sell yourself at a true market rate. No one feels disappointed that your last season wasn’t as good as your age-23 season, so you get paid for what you can do, not discounted for what you can’t do anymore.

Rick Ankiel: A case study in the consequence of a fractured, piecemeal career, Ankiel was a wildly well-liked young pitcher who went mound-nuts too soon to get paid for that and who never had a consistent enough offensive season to get paid for his solid skill set as a position player. He made only $12 million and change over a career that promised so much more, more than once. (Incidentally, Mark Prior earned almost exactly the same amount.)

Joe Carter: Sam was right to recite the old bromide, the moment he heard Carter’s name: “The money lies in the RBIs.” Indeed, despite being a terrible player for years (a very low OBP and brutal defense canceling out the value of his power), Carter made over $47 million, and was one of the highest-paid players in the league for a while there.

That’s actually not why I selected him, though. Rather, I chose Carter because one of the seasons during which he was the AL’s richest player was 1993, the same year he hit the famous, game-ending, city-rending home run to give the Blue Jays their second consecutive World Series title. It fascinates me that I didn’t know it sooner: The fates called Carter to bat, the most expensive player in baseball to take the most important at-bat of his team’s season, and Carter put his bat where all that money was. It’s a rare case in which knowing how much a player earns actually enhances my enjoyment of an on-field moment, even if only in retrospect.

Jason Kendall: My fascination with Kendall stems mainly from being a Cubs fan of just the right vintage. My first season following the team was the same as Kendall’s sophomore campaign, 1997. I watched Kendall regularly thump the Cubs, and do so in ways that catchers didn’t usually do it: He would hit triples, steal bases, bat .310, avoid double plays well. Despite taking plenty of foul tips while catching, he gleefully took plenty of pitches on the elbow and shoulder, boosting his on-base percentage. In 1998, he had 56 infield hits. He hardly ever struck out. He really did it all.

For all those reasons, I wanted Kendall desperately, for the Cubs. I envied him through the careers of Scott Servais, Sandy Martinez, Tyler Houston, Jeff Reed, Joe Girardi, Robert Machado, Damian Miller, Paul Bako, Michael Barrett and a host of other middling backstops. At long last, though, I essentially gave up on him.

Then, suddenly, there he was. The 2007 Cubs were in the hunt for the NL Central title and needed a catcher badly, so in July, they added Kendall, by then nearly washing out of the league for the Oakland Athletics. He would take about 200 plate appearances for the Cubs that summer and fall, posting a terrific .362 OBP, infusing them with just enough extra lineup length that the team overtook the Milwaukee Brewers and won the division crown. I went to 12 of their last 15 home games that season, as a freshman in college, and was the only person disappointed each time Geovany Soto got a start instead of Kendall during September. I still have a Jason Kendall shirsey, purchased for a pittance after he signed with Milwaukee that winter.

Kendall made over $83 million in his career, a thoroughly remarkable three-year peak baiting the Pirates into signing him for six years and $60 million, just before injuries and a high workload in his early years began to eat away at his value. The thing that interests me most, speaking objectively now, is how many people would likely be stunned by that number. Kendall is perceived, I think, as a journeyman, an injury-ravaged yeoman but nothing more. He was scrappy, sure, but Kendall was a superstar at his best, and it seems to me he’s remembered too much for his career’s second act, too little for its first. Eight times, Kendall led his league in games caught. Thirteen times, he was in the top five. He was as durable as his peak was electrifying, and as a result, the numbers say he was actually about 75 percent of a Hall of Famer. He’s not likely to see a second season on a Cooperstown ballot, though.

Curt Schilling: Famous and infamous for being a smart, ambitious, aggressive guy, Schilling made $114 million and change over a nearly-20-year career. He was so savvy, or thought himself to be, that he at least partially represented himself for a stretch later in his career. I wanted to see how well he leveraged that business sense. John Smoltz is a very fair comparison for Schilling, though, and he made a shad over $127 million, so being a sharp guy didn’t make Schilling any extra cash. If only it had, maybe he could have kept his video-game company afloat.

Gary Sheffield: Not only was Sheffield his own agent toward the end of his playing days, but he served as an agent himself after retiring. He made over $168 million in his career, and was the highest-paid player in MLB in 1998—while playing for the scorched carcass of the defending champion Florida Marlins.

Did I say a few notes? Oops.