Pete Rose and Software Rearchitecture:
Yup, the two are related

Children of the ’70s may remember Pete Rose, aka Charlie Hustle, as a superb, hard-charging Cincinnati Reds baseball player with a Popeye physique. Millennials may remember Rose as the Reds’ manager banned from baseball forever for betting on games. A spectacular, Rudy Giuliani-like fall from grace.

What does Pete Rose have to do with software rearchitecture? Plenty.

The most fraught words a CEO will hear from a CTO are, “We need a complete software rearchitecture.” Visions of months, possibly years, of software rewriting resulting in a lesser-featured, buggy release dance like rotten sugarplums before the CEO’s eyes.

A CTO may have excellent reasons for recommending a redo from the ground up, including:

  1. Changes in company direction may require functionality never imagined in the original design that cannot be well-supported without significant change.
  2. Survival was the big worry at the company’s outset and the architecture to support an imaged future was never well-considered.
  3. Over the years, the unchecked piling-on of features atop a brittle foundation results in a buggy, poorly performing product that mere tweaks can’t fix. Moreover, when multiple teams work in the codebase, interdependencies cause the software to break in unexpected places.

But, caveat emptor. Regardless of all the great reasons for a total redo, software folks have an annoying propensity to reject the work of their predecessors. Since a CTO can’t pee on a Github repository, tossing out old work to create something brand new is the high-tech way to mark one’s territory. Furthermore, the lure of restarting with a blank canvas is irresistible to an ambitious CTO.

Regardless of a CTO’s motives, a rearchitecture project is a ballsy, big-vision move. Since there are no short-term wins from software rearchitecture, these projects are more a marathon than a sprint. Done well, scorched earth redos may save companies from failure and ensure future growth trajectory.

Feature-crazed customers typically look askance at forfeiting short-term wins for long-term gains, so it’s a tough sell for Product Managers and Salespeople. Furthermore, once potential customers sniff out a new product in the works, sales of the old product may tank.

Back to Pete Rose. Charlie Hustle became a hustler, betting on football and basketball. After an investigation, Rose admitted he also bet on his baseball team to win. Is this a crime, having such confidence in the team he manages that he lays down beaucoup Benjamins? Wouldn’t it be worse if Rose bet on the Reds to lose and sabotaged the team?

Yup, it’s terrible that he bet on his team, win or lose. If the Reds were structurally unsound, instead of re-architecting and rebuilding the team for the future, Rose was motivated by his bets to make a few short-term strategic trades to plump up his roster for immediate wins. Instead of taking long-term action to benefit stakeholders and fans, Rose acted in his self-interest with his short-term bets.

Rose was banned from baseball in 1989 by baseball commissioner Bart Giamatti. Subsequent commissioners through the years agreed that Rose’s betting on his team was such a heinous breach that they continued to uphold his lifetime ban from baseball. No Hall of Fame. No Cincinnati Reds old-timers games. No more managing Major League Baseball teams.

The public is accustomed to public servants acting selfishly and not in the best interests of constituents: A President who used the office to enrich his coffers; a Supreme Court justice who refused to recuse himself when faced with an apparent conflict of interest; a Senator, richly funded by oil companies, who derails green initiatives. Sadly, poor old Charlie Hustle is the only one taken to task for his deeds and his offense is arguably the least egregious of the lot.

Most commonly, CTOs who push for a grand rearchitecture probably do so for good reasons while also possessing some degree of megalomania. Unlike scoundrels out to serve only themselves, a CTO with the guts and wherewithal to rearchitect a product should get a fair hearing and most likely a green light.