Recently, on the NBA Network I caught the tail end of a conversation between Kenny Smith and another announcer about the LA Clippers. Maybe there are less successful franchises by some metric, but the Clippers must be in the mix in any discussion of trees that never bear fruit (see Pro Basketball Reference). If this season's trend continues, the Clips will record 1 winning season in the last 14 and 2 out of the last 18. In half of these seasons, they have won less than one-third of their games.
Long losing streaks (for example WKU football) or extremely few wins in a given season (Nets last year) attract unwanted attention, derision, pity, and fan frustration. Even teams with modest or substantial success but no championships maybe treated as failures -- an overly harsh assessment by my way of thinking. From an managerial econ standpoint, the systematic, year-in-year-out-losing of teams like the Clippers provide a more compelling case for analysis. It's unlikely that this level of impotence arises merely out of bad luck. It screams bad management and poor decisions, especially in view of reverse-order drafts, limits on free agency for young players, and salary caps.
The broad, pat answer is bad ownership. Donald Sterling has owned the team since 1981, overseeing three decades of dismal performance. (Ironically, it has been reported that he has recently heckled the team for its poor performance. Maybe he was heckling himself.) Ok, bad owner. Mainstream journalists derive great pleasure in trashing rich-guy owners -- easy targets -- but the rants don't really dig out the managerial explanations.
Possibly, the ability to make money from the team without putting out a decent product is another broad answer. Poor incentives -- poor performance. This certainly stands a chance of being right and it's an easy target that I've often heard. My roommate in grad school, a Buffalo Bills fan, laid this charge at Ralph Wilson's feet. Over the next decade, the team performed very well. Many Reds and Bengals fans made these charges at Marge Schott or the Browns at various times in the 1980s or 1990s, only to see success around the corner. While incentives matter, most sports owners seem to enjoy both winning and making money. Their wealth speaks to their affinity for making money; buying a sports team, in itself, is a case for an interest in winning. There a lots of other investment opportunities out there.
So, if I assume Sterling likes to make money but also wants to win, what is at the root of the Clippers problems? I have not done an extensive case study of the Clips -- a good Harvard Business School case. No doubt, personnel decisions must be examined. In times when many owners are criticized for dumping their coaches and other subordinates far to0 quickly, it's hard to make this charge of Sterling. He kept Elgin Baylor in the post of VP over basketball operations from 1986 to 2008. (In a Clipper-esque twist, Baylor sued the Clippers for underpay and firing based on age and race). Sterling/Baylor stuck with Mike Dunleavy as head coach and GM for most of 7 seasons in spite of only one good year. Over the years, the Clips have not recycled the perennial losing coaches (the Kevin Loughery Syndrome). Instead, Dunleavy had some success in Portland. Before him, they recruited respected people like Bill Fitch, Chris Ford, Alvin Gentry, who ran the gambit agewise from older, medium, to younger and crossed racial lines.
In his NBA Network comments, Kenny Smith emphasized lack of attention to doing things that attract and retain good people (a theme of "Rochester" managerial thinking).
As Kenny Smith emphasized that the interest and culture in attracting and keeping good people manifest in a variety of ways. As an example, he explained how at UNC, Dean Smith made his players a priority. Dean Smith was in charge. Players played his way, but Dean Smith was always accessible to them. Kenny Smith noted how even after his playing days ended, he could call Dean Smith's office and immediately speak with the coach unless he was on the line with someone else, and then he could expect a return call within 10 minutes. In contrast, when drafted by the Sacramento Kings in 1987 as the 6th overall pick, he called the Kings office one day to speak with the coach. The office assistant put him on hold for 10 minutes. When the assistant returned, the question was 'now who are you?', an indicator in Kenny Smith's eyes of the enormous gulf in player management at the two places.