With their backs against the wall, monetarily speaking, and the club’s playoff chances quickly dwindling, Cleveland famously – or infamously, depending upon your locale I would guess – dealt away reigning Cy Young Award winners in back-to-back seasons, becoming the first franchise in MLB history to pull off the feat.

And for the first five seasons after dealing their pitching stalwarts, it looked as if all the front office had to show for their collective efforts was a league average regular left fielder, who hit like a center fielder and lacked the pop for a corner spot, and a frustratingly fringy back-of-the-rotation arm. They were, in every sense of the word, the last men standing from their respective deals as the other prospects petered out.

Something funny happened over the past season-plus – not funny in the traditional sense, mind you, but more in the way of nobody-saw-it-coming – both players took developmental leaps forward. The corner outfielder hit like a legitimate middle-of-the-order impact bat and the maddening, inconsistent right-hander suddenly became, well, consistently dominant.

Conventional baseball wisdom suggests – or dictates – that trades cannot be observed as an immediate gut reaction, but rather as a past event viewed several years after the fact. So let’s play devil’s advocate for a bit and look back more than six years later at each trade, deciding if the club would pull off the same exact deal again.

The C.C. Sabathia Trade

Sabathia was never going to re-sign with Cleveland. The fans knew it. The local media wrote about it. And once the big southpaw rejected the club’s four-year, $72 million offer that spring, the front office had to realize he was already playing with one foot out the door. The Tribe’s early season collapse after their magical postseason run only hastened his departure. Enter the Brewers, who were fighting tooth-and-nail to stay in the mix atop the NL Central Division.

On July 7th, 2008, the Indians sent Sabathia to the land of Uecker for a quartet of youngsters: centerpiece Matt LaPorta, southpaw Zack Jackson, right-hander Rob Bryson, and a PTBNL. The Indians brain trust was reportedly torn between Taylor Green and Michael Brantley before settling on the latter.

In the following years, Sabathia would immediately walk away from the Brewers to sign a huge deal with the Yankees. LaPorta never put it together despite some pre-trade dominant Southern League numbers. Jackson was eventually flipped to Toronto, and Bryson tossed only a handful of innings above Class AA.

For his part, Brantley was the quintessential league average performer over his first three full seasons, tallying 5.7 fWAR between 2011 and 2013. But the former seventh round pick took a gigantic developmental leap forward in the game’s most deficient area last season: he started hitting for power, something he had never shown at any point in his entire professional career. He would post his first 20/20 season en route to becoming the seventh most productive hitter in the big leagues last season, trailing only Andrew McCutchen, Mike Trout, Victor Martinez, Jose Abreu, Giancarlo Stanton, and Jose Bautista in wRC+.

One more interesting note: Brantley’s wins above replacement last season, according to FanGraphs, was nearly identical to Sabathia’s peak while not wearing an Indians uniform (6.3 vs. 6.4).

So would the Indians pull the trigger on sending Sabathia to Milwaukee again? Without a doubt. In my opinion, a good rule of thumb would be if a team acquires a prospect that produces – even for one season – anything in the neighborhood of the departing player after the trade, it is a slam-dunk home run.

The Cliff Lee Trade

There are actually a lot of similarities between the packages received by the Indians from both blockbuster trades:

• Cleveland acquired four players in each deal (though they did ship Ben Francisco to Philadelphia as well)

• The centerpieces for both deals – LaPorta and power right-hander Jason Knapp – never even came close to reaching their suspected potential. Note 1: the Indians acquired Knapp with knowledge of a pre-existing shoulder injury. Note 2: Knapp resurfaced on the Rangers’ High Class A team last season for the first time in four years.

• The third and fourth prospects acquired in both deals are no longer in MLB associated baseball

• And, finally, the players viewed as the second best prospects were the long-lasting, impactful players

Baseball America routinely mentioned Carlos Carrasco among the game’s prospects, listing him as the 41st, 54th, and 52nd best minor leaguer beginning in 2007. But unlikely Brantley, Carrasco was largely a quasi-replacement level performer for the Indians pre-2014: he would total 1.3 wins above replacement in 239 innings.

But he, too, blossomed last season, showcasing a remarkable ability to front a rotation with his rare swing-and-miss-while-limiting-free-passes ability, something that’s continued over to 2015 as well.

Among all pitchers with at least 170 innings since the start of 2014, Carrasco ranks seventh in punch rate (9.7 K/9) and fourth in xFIP (2.67) – all while walking fewer than two batters every nine innings. He’s equaled Gio Gonzalez’s totaled production despite throwing more than 20 innings fewer.

So, would the Indians pull the trigger again on the same deal with Philadelphia?

Yes, I would say so. Carrasco has teamed with reigning Cy Young Award winner Corey Kluber and Arizona castoff Trevor Bauer to give the Indians a triumvirate of power arms atop the rotation.

Now, admittedly, knowing what we know now viewing both of these trades look like solid deals for the Indians, but that wasn’t the case a mere two years ago.

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For more analysis check out Joe Werner's site: ProspectDigest.com. You can follow him on Twitter at @JoltinJoey .