When the Cubs signed Milton Bradley, there were all sorts of reactions-enthusiasm for what the switch-hitting slugger might provide in terms of lineup balance, but also concern over whether his particular brand of charm would play well before the well-suds’d legions in the stands. While we’re already being treated to seeing both sides of that particular proposition as far as the costs and benefits that come with employing the almost reflexively-labeled “mercurial” Milton, rational observers wondered whether a player with his spotty track record for staying healthy would be able to repeat the brilliant comeback campaign he had DHing for the Rangers in 2008. Not only was he being paid at a level that reflected a happy faith that he could, he was being challenged by the Cubs to try and repeat that level while also rising to the challenge of playing right field regularly in the DH-less National League.

Since its inception, arriving at DH during a career has been something of a professional end point-setting aside the extreme defensive indifference of someone like Dave Kingman, it’s where players go towards the tail end of their careers, and usually because of one kind of incapacity or another. Say, the knees of Harold Baines or Andre Dawson, or the bum wings of a Don Baylor or a Hal McRae, or acquired reps for all-around fragility that pushed Paul Molitor or Edgar Martinez toward one-dimensional greatness.

With time comes change, of course. We can readily recognize that we’re at a point in the game’s history where playing deep into your thirties isn’t all that unusual, assuming a certain skill in the first place. Contributing to that longevity is the ever-improving prowess of the game’s training staffs and the advancements in sports surgery. Surely that might suggest that Bradley’s going to be better able to handle everyday play in the outfield in what is only his age-31 season, right?

Well, maybe, but if we instead use history as our guide, the track record isn’t exactly replete with recent success stories of hitters who moved from regular DH duty to regularly playing a position, let alone a spot in an outfield corner. Let’s start out with what Bradley did last year: 97 games at DH, and 20 in the outfield. Let’s use that very number of games, 97, to generate a standard for basic regularity, and use that for both the year as a DH, and then for the next year as a fielder as well. How many players have been able to do that?

Using this standard and going back to the inception of the designated hitter for the 1973 season, it has happened exactly 13 times, and twice by a single player. In 1977 and 1978, we get an initial pair-Eddie Murray and Jim Rice were regular DHs for the Orioles and Red Sox (respectively) in ’77, which might seem strange to us today because Murray was a 21-year-old rookie while Rice was a young veteran but only 24. In each instance, established veterans-Lee May in front of Murray, and Carl Yastrzemski giving the Monster one last go-were getting spins at their favored spots, and the ’70s were hip to experimentation when it came to young people doing new things. Their career paths prefigure similar roads taken by Frank Thomas in 1991-92, Albert Belle in ’92-93, and Carlos Delgado in ’96-97. Since all were young hitters at the outset of their careers, this doesn’t really help us much when it comes to Bradley.

After Murray and Rice, Don Baylor was the next player to make this kind of shift, going from 102 starts at DH in ’78 (plus 39 in left and 17 at first) to 97 starts between right and left and 65 as the DH for the division-winning Halos in ’79. He did the latter as a 30-year-old; he would also revert to DHing for the balance of his career from there on out, making just 84 more starts as a position player over the remaining nine years of his career. In contrast, Greg Vaughn was given a shot as a regular DH by the Brewers in ’95 as a 29-year-old to rest his bum shoulders; he didn’t hit well as an everyday DH, so the Brewers pushed him back out to left in ’96.

We have the more recent examples of Mike Stanley (’98-99) and Rafael Palmeiro‘s double dip (’99-00 and ’03-04) of peregrinating between first base and DH; both were veteran players who were being adapted as their teams shifted personnel, and both would DH and play first, because they were still in the American League. Also working with the benefit of staying with the same team in the same league are Matt Stairs‘ move from DHing for the ’98 A’s to starting for them in right field in ’99, and Raul Ibanez going from regular DH duties with the Mariners in 2005 to playing left almost every day in ’06. If you’ve noticed something about Stairs’ feat, you should-he is the only player to go from regular DH work in one season to regular work at a position other than first base or left field in the next.

With the minor exception of Vaughn’s trade to the Padres in ’96 for their stretch drive, these 11 of the 13 all had the benefit of staying in the American League. In other words, none of them did what Bradley’s going to have to-go from regular DH work in the AL to regular position-playing work in the NL. That’s something only two players have ever been asked to do, and both were first basemen: Al Oliver, moving from DH duty with the Rangers in 1981 to starring at first base for the Expos in ’82, and Jack Clark‘s escape from the Yankees after DHing for them in 1988 to go back to first base for the Padres in ’89. That was 20 years ago.

Which leaves us with some pretty thin gruel as these things go: since the institution of the DH rule in 1973, we effectively have just two players who have made the jumps from DHing in the DH league to playing a position in the senior circuit, and we have exactly one player who has made the jump from DH to right field-Matt Stairs, not someone anybody confuses with the concept of defensive excellence-in that same stretch of time. As much progress as has been made keeping players healthy late into their careers, we’re left with Bradley’s status as a player taking on a unique challenge, and that’s without getting into his managing just 245 starts in the field over the last four seasons, and not a single 100-game season in which he wasn’t a full-time DH. If he can do that, he’ll have accomplished a new testament to the skill we’ve been waiting to see since his debut a decade ago.

A version of this story originally appeared on ESPN Insider Insider.