In the aftermath of the Arizona Diamondbacks non-tendering Joe Saunders — the mediocre left-handed pitcher who was the only Major Leaguer in the package sent by the Angels to the Snakes for Dan Haren in July 2010 — last month, it occurred to me that despite the fact that the franchise has only been in existence for 14 seasons, there’s a strong possibility that the Diamondbacks have been the greatest off-the-field thorn in the Yankees’ side of any team in Major League Baseball in recent history*.

* Though it’s not as if they’ve been pleasant to deal with between the lines either, given that they were responsible for perhaps the most heartbreaking loss an entire generation of Yankee fans have ever experienced in the form of Game 7 of the 2001 World Series.

Anecdotally, we’ve heard stories detailing a mutual dislike on the part of former Diamondbacks owner Jerry Colangelo and George Steinbrenner, both known for their hard-nosed ownership styles, and as best I can tell the problem initially stemmed from a now-famous meal shared by Steinbrenner and David Wells in January 2002, in which the Boss re-signed Wells four days after the burly lefty reached a handshake agreement with the D-Backs.

This incident no doubt left Colangelo steaming, and it would come back to bite the Yankees in the 2003-2004 offseason, as the team desperately needed to upgrade a rotation that was losing three-fifths of its members. The Yankees were very interested in Curt Schilling, but the talks didn’t go anywhere as Arizona’s asking price — which appeared to include both Nick Johnson (coming off a 2.1 fWAR season) and Alfonso Soriano (5.0 fWAR), at the very least — was rightly deemed excessive. It’s unclear who Cash may have been willing to part with, and whether talks ever progressed between the two teams, but before they even had a chance to Theo Epstein and Boston swooped in, joined the Schillings at their Thanksgiving table, and somehow convinced the Diamondbacks to trade Schilling, coming off thee seasons in which he racked up 7.6, 9.7 and 5.9 fWAR, respectively, for a package headlined by Casey Fossum and rounded out by Brandon Lyon and minor leaguers Jorge De La Rosa and Michael Goss.

In a vacuum I suppose that’s a fair amount of talent for Boston to have surrendered, but in hindsight it turned out to be an absolute steal for the Red Sox, as Fossum was basically never an effective pitcher again following the deal; Lyon’s carved out a career as a pretty good middle reliever, the most fungible asset in all of baseball; De La Rosa’s been a #3-ish starter at best in the National League and Goss never made it to the Majors; while Schilling accumulated 17.8 fWAR in four seasons with the Sox while helping lead the franchise to its first World Championship in 86 years and another three seasons later.

While you could drive yourself crazy playing the what-if game, it’s probably fairly safe to say things would’ve unfolded quite a bit differently had the Yankees acquired Schilling that offseason instead of the Red Sox.

Of course, the Yankees finally did get a Diamondback ace of their own the following offseason, in Steinbrenner’s long-coveted Randy Johnson. The Big Unit had a strong debut season in pinstripes in 2005, but was pretty mediocre in 2006, and famously flubbed both of his postseason appearances. Fortunately the Yankees likely didn’t regret the cost to acquire Johnson — Javier Vazquez, coming off an execrable first season in pinstripes, along with Brad Halsey and Dioner Navarro — especially considering that prior to the deal being executed Robinson Cano had been a long-rumored chip in a potential Johnson trade, but in hindsight I think this can still be considered another low point in the Yankees’ and Diamondbacks’ mutual history.

Following his disappointing 2006, the Yanks decided they’d had enough of Johnson — who, as it so happens, expressed a desire to return to Phoenix — and shipped him back to the Diamondbacks for nothing special in Alberto Gonzalez, Steven Jackson, Ross Ohlendorf and Luis Vizcaino. I suppose receiving four warm bodies for a pitcher who appeared to be well past his glory days is somewhat commendable, though Johnson still went on to put up two more decent (if injury-plagued) years out in the desert, while the 2007 and 2008 Yankee pitching staffs weren’t exactly anything to write home about.

The Yankees and Diamondbacks hooked up again in December of 2009, in the three-way trade that brought Curtis Granderson to New York and shipped Ian Kennedy to Arizona, a deal that also saw Detroit send Edwin Jackson to the D-Backs but also gain Austin Jackson and Phil Coke from the Yankees and heist Max Scherzer from the Snakes. Two years later this would appear to be the rare three-way trade in which all involved parties appeared to benefit. I’d do this deal all day every day, although it somehow figures that Arizona would wind up turning Ian Kennedy — who I maintain would never have become a 5.0 fWAR player in the Bronx — into a frontline starter.

This brings us back to the Saunders-Haren trade of July 2010. Granted, the Angels also sent Tyler Skaggs — currently ranked by Baseball Americas as Arizona’s 3rd-best prospect — Patrick Corbin (10th in the system) and Rafael Rodriguez to the desert in the deal, so it’s not quite as cut-and-dry as just “Saunders-for-Haren,” but given that Saunders wasn’t even retained by the D-Backs a mere year-and-a-half after being acquired, while Dan Haren has been a top 10 pitcher in baseball the last two seasons, it’s difficult not to wonder how things might have played out had the Yankees and Diamondbacks managed to consummate a deal.

It’s difficult to say given that all we really know is that Joba Chamberlain’s name was the primary one bandied about during the trade talks of July 2010. If we were to try to build a comparable package to the one Arizona received, the Yankees’ #3 prospect at the time (per our own Mike Axisa) was Manny Banuelos, while #10 was Jose Ramirez. At the time, would you have been willing to trade a package of Joba Chamberlain, Manny Banuelos, Jose Ramirez and some low-level filler for a 29-year-old Dan Haren? Pretty sure I’d have been willing to pull the trigger on that one.

Again, we have no idea whether something like that was ever offered and/or whether it would have been an acceptable haul for Arizona, but on paper it seems like a pretty fair swap, especially when you consider that Saunders has been worth 2.7 fWAR in two full seasons of starting while Joba has been worth 1.8 fWAR in a season-and-a-half of relieving during that same time period. You have to figure Arizona almost certainly would’ve given Joba the chance to start that the Yankees never will, and the Yankees would’ve had a right-handed ace to complement CC Sabathia.

Of course, at the end of the day the majority of this is hearsay and conjecture, and there’s no way of really knowing whether Arizona has had it in for the Yankees over the years. However, as I’ve illustrated above, the two teams’ transaction history — and it certain cases, lack thereof — would make me considerably wary of doing business with Arizona in the future.