After the girl you fell in love with in middle school, but never even spoke to, came the girl you fell in love with in high school, but not deeply enough to keep you from making out with her best friend a week before prom. After her came the girl you fell in love with in college, the one you idealized, the one you fell out of love with once you found out she wasn’t perfect.

And after them came Brett Jackson.

I married the only woman I ever dated, and we’re happier than ever, three years and two kids in. I haven’t broken any hearts or had my heart broken, at least in love. In baseball, though, as a Cubs fan, I’m something of a heartbreak expert. I’ve gotten excited about Cubs prospects who never got out of Double-A (hai, Nic Jackson). I’ve built up Corey Patterson and Roosevelt Brown and Hee-Seop Choi into far more than they could ever truly be, then gotten mad and sad when they fell flat. I’ve weeped over the losses of Bobby Hill and Jose Ceda, even though I deserved better, anyway.

With Brett, I thought I had avoided all of that. I thought I had learned not to be irrational, or to get too attached. I thought I had modulated my expectations. I thought I fell in love in a mature way, a responsible way. But Brett broke my heart, anyway.

Jackson may or may not survive the winter on the Cuba’ 40-man roster. It only just barely matters. He’s probably never going to see the big leagues again—although he could. In his lone stint with the Cubs, which lasted 142 plate appearances in 2012, he hit .175/.303/.342, which isn’t all that terrible. However, he also struck out 59 times in those trips. The consensus was that he needed to make a change, so he tried some swing-mechanic fixes in Spring Training 2013, but injuries and an inability to succeed after those adjustments derailed his season, and probably his career.

As you always do when the relationship you thought you would finally make work doesn’t, I like to think it could have worked, in another time, another place. Jackson is a stunningly close comp for Rick Monday, the first player ever drafted by an MLB team. Monday was a center fielder, but was a bit big for that gig, and had only a few years where his defense was even average for the spot. He also struck out a lot. In fact, in his two best seasons, he struck out at more than one and a half times the league-average rate. That was in his very best seasons.

Thankfully, though, the league-wide whiff rate in his day was only in the 15 percent range, even a bit lower. Monday could strike out as often as any regular in baseball, and still be on the good side of 25 percent in most years. That figure doesn’t preclude good overall offensive stats, and indeed, Monday (with a long, sweeping, fairly level swing, and with forearms literally larger and more toned than his biceps) hit for very good power, and took a large number of walks, virtues that far outran his vice.

Maybe Jackson, if he had played then, would strike out every bit as often as he has in his career, including that hideous number north of 40 percent in his lone big-league audition. It’s fair to wonder whether Jackson’s swing was just too long to catch up to good pitchers’ fastballs, once they got him thinking about other offerings. It might be that league-wide strikeout rates depend more on how ballplayers are chosen than on things (like the composition of the ball, the rule-book strike zone and pitcher usage) that have changed so violently in the 40 years since Monday’s prime.

It seems more likely to me, though, that strikeout rate, like home-run rate and overall run scoring and most other statistics, rise and fall for everyone at certain points. I think Jackson, if he could plan on hitting 89 miles per hour most of the time instead of facing so many pitchers who routinely touch 94 or 95, would strike out only as often as Monday did, and would therefore be a very productive hitter. He has power and speed very much in line with Monday’s. He walks a lot, just as Monday did. He even walked 15 percent of the time in his truncated trip to the Show.

Prospects will break your heart. You can’t protect yourself by falling only partially in love, or by striving to understand and embrace the guy’s warts. You can’t time-travel, and make a guy a viable player by putting him in a context that works better for him. Brett Jackson will always be the painful reminder, for me, that there are a whole lot of ways to not become a good player in Major League Baseball, and that the flameout rate among even seemingly safe prospects makes the percentage of relationships that fail look measly.