The Art Of The Next Best (2 page)

There was the play area at Children’s
Hospital and the wing at the Museum of Fine Arts that bore his
name. A major donor to the Republican Young’s campaign PAC when he
ran for governor...and then an even larger donation to the Democrat
Kirk’s campaign during the next cycle. But those were big, splashy
expenditures, and Alex had never struck Martin as splashy. He kept
looking; it was the little things he dug into because that was
where someone like Alex would have dug too. Donations to almost
every city councilor’s campaign for the last twenty-five years. And
then the mayoral campaigns. “Even Fletcher, you son of a
bitch.”

Boston was many things and all at the same
time. The mayors and most of the at-large councilors were expected
to bridge those distances in public life, but not the district
councilors. Alex didn’t donate to them out of political affinity;
he donated for influence.

But wasn’t Boston the small ball BS someone
like him would want to avoid? Or was it?

There was no point in researching Alex’s
career before he took over Gerald Hendrickson’s investment firm.
Thanks to Teague he knew that his initial investment had been in a
South Korean electronics firm and the seed money had come from
Gerald himself. The price had been Lucy delivered to his
unsuspecting son Jim, and none of that would have been possible if
Jessie’s father Tom hadn’t ratted out his own sister. His price?
Enjoying the look on Alex’s face as he described raping Lucy’s
girlfriend.

“Douchebags,” Martin muttered to himself.

But what had he done then?

The local press couldn’t shut up about Alex
Sheldon after 1989 when he was named Boston’s Most Eligible
Bachelor. Hindsight was perfect, but Martin couldn’t believe that
no one had seen through Alex’s strategy to seem aloof and secretive
and then annoyed by the “honor”. That had only whetted the media’s
appetite. The deals were even bigger, and the women on his arm were
even more beautiful...though none ever matched Tatiana Hamilton,
Miranda’s mother.

But it was the eight years between his
initial success and his explosion into national and international
media coverage that were harder to dig into. When the
Globe
or
Herald
mentioned him, he wasn’t on the front page of the
business section much less the paper as a whole. And most of the
time his name wasn’t mentioned at all, just his holding
companies.

“And why are you so cheerful?” Jessie asked
when they were laying out the takeout on the coffee table. “I asked
if you were okay with Thai food and you said yes.”

“Pad See Ew is my life,” Martin said
absently.

“Then smile.”

“I can’t,” he whined. “I have to look through
eight years of financial prospectuses tomorrow.”

“Better you than me, my man,” Jessie said as
she forked Pad Thai into her mouth.

A month later, he understood.

For all his reputation as a brilliant
investor, Alex had never taken anything other than a
well-calibrated risk. The investments he’d made had been safe, easy
bets. And for someone who saw business as war, the safest bet was
an enemy who couldn’t fight back. Even better: one who wasn’t
worried about an attack.

The factory in Mattapan was an anomaly; not
the buyout or the jobs lost but the fact that he let his name be
associated with it. There was an angry editorial—not an opinion
piece, but an editorial that the entire board signed off on—that
condemned what they knew was the beginning of the decimation of a
community. But then nothing...until a week later when the fluff
piece about his selection as Boston’s Most Eligible Bachelor was
published.

It had been an experiment to see how much
damaging publicity he could withstand.

Martin strummed his fingers on the desk, then
decided he needed to take a walk on Columbus Avenue.

He remembered what he had read as he started
out at the Roxbury-South End line. The area surrounding the
University was very late to gentrify, which he’d always thought of
as odd. Lucy was a good investor, but she also knew how to hurt
someone where they lived, and everyone knew Alex lived in his bank
account.

Alex Sheldon made his “strategic investments”
where he did because he could. No one was looking, and if they were
he had bought himself a shrug. Boston was—and could still be—a
machine if you knew where the right buttons and levers were.

But Martin had to give credit where it was
due. Alex was nothing more than a clever hacker who could figure
out how something was built and how it could be taken down; it was
the engineers who should bear the greatest burden.

Mayor Dan Green had fervently tried to patch
the machine together as it started falling apart after years of
disrepair. His successor Ron Fletcher had made a big show of how
hard he was trying to fix certain parts while using an outdated
repair manual. But it was Angelo Cervino who had calmly figured out
where the wiring was most vulnerable and where his biggest gains
could be made.

He was a politician who had looked at areas
that were festering, put on a couple of bandaids and let people
thank him for not being his predecessor. For his first three terms,
that had been enough.

And Alex Sheldon had been donating to Cervino
from the moment he set foot in office.

He looked back through the financial records
political donations. Almost every candidate for councilor and
mayor, but not Jack Donnelly or David Hwang.

Martin didn’t have to ask why David Hwang
wouldn’t take money from him Alex. He was Lucy’s protégé, and if
he’d needed the money, she would have helped him find other donors.
Besides, Alex had fled Boston by that time.

But what about Donnelly?

Let Downtown, City Hall and Back Bay tell
themselves whatever they wanted, but there were three nexuses of
power in Boston: Dorchester, West Roxbury (never to be confused
with Roxbury) and South Boston. (Politics 101: areas with the
biggest voter turnout wins.) Maybe South Boston didn’t always turn
out for the best reasons but turn out they did. And when they did,
for the last fifty years, they turned out for a Donnelly if one was
running.

John Matthew Donnelly has been a supporter of
Edward Brooks, the state’s first African-American Senator. His son
John Christopher, a State Senator, had felt that both Governor
Dukakis and Mayor Green were selling Boston out and allied himself
with the politicians who fought integration tooth and nail. He
embraced Fletcher’s campaign for mayor, but stepped down right at
the time Cervino came to power.

John “Jack” David Donnelly went to law
school, worked in his father’s law firm and made noises about
“neighborhood schools”, but otherwise looked like he was on track
to become Massachusetts Attorney General. His record as a U.S.
Attorney earned him a lot of praise from both sides of the aisle,
and it was an open secret that the AG had offered him a job. But
then he surprised everyone and ran for City Council.

The
Boston Globe
wasn’t what it had
been for a decade, but it was still the place to turn to for facts.
If you wanted gossip and rumors, the place to go was the
Boston
Herald
.

The
Herald
had remarked, with their
usual snark, that while Donnelly seemed to be a shoe-in during his
first run, he was spending as little money and time campaigning as
he could. “Only a name like Donnelly in today’s South Boston could
get away with the phoned-in campaign Jack Donnelly is mounting.
Someone even said that they’d send a life-size picture of his
father over in his place. Doesn’t seem to be hurting him.”

“Donnelly Junior has miraculously avoided
being asked why he’s running,” another piece read. “Might that have
something to do with the fact that Donnelly Senior has been making
phone calls himself before all interviews and ordering journalists
to stay focused on the issues? If you don’t realize that Senior is
the man behind the curtain, promise to bring someone with you when
you see
The Wizard of Oz
for the first time. I wouldn’t want
the movie to scare you too much.”

Martin came away from the pages he read in
the
Herald
convinced that Donnelly ran—and won—because his
father had wanted him to. Some people, he supposed, could make a
dynasty work better than others. Some might have argued that it was
his birthright to be the president of the City Council.

But mayor? The Donnellys were judges,
representatives, senators and city councilors, but none of them had
ever been mayors. If Fletcher hadn’t been offered the
ambassadorship to the Vatican, there was every reason to believe
that he might have helped ease John Christopher into his seat
during the next cycle. But on this Donnelly Senior never said a
word. He was clearly too old for a run now, but unlike old
soldiers, ambitions don’t fade away; they’re just transferred.

What might have happened if Donnelly hadn’t
run for mayor during the same cycle that David Hwang had? David
Hwang didn’t do politics nearly as well as the Donnellys, but from
his first run for City Council it was impossible not to be charmed
by the intelligent and earnest young man who had worked to make
life better for people left behind by the New Boston. He was the
technocrat savior. So what did that leave Donnelly? Being cast as
Cervino-Lite.

No matter how much he read, Martin still
didn’t understand why Donnelly had chosen that cycle to run. Yes,
Cervino had made it clear that he was going to run for a historic
fifth term, but after that there had been whispers that even the
Globe
had picked up that he looked favorably at
transitioning the office to Donnelly. There was only one
explanation that made any sense to Martin: someone thought Hwang
had a really good shot at a win.

From his first class as a freshman Poli-Sci
major, Martin had understood that politics was rarely about policy.
So it didn’t matter that Donnelly’s proposals were milquetoast
pitches married to reform rhetoric. Yes, he wanted to change the
schools—every mayoral candidate for the last sixty years had wanted
to change the schools—and yes, he promised to blow up Cervino’s
stronghold, the Boston Redevelopment Authority—but he didn’t make
noise about any of his other proposals, including increasing the
youth street workers’ budget, investing in community center and
library upgrades and increasing access for community outreach
workers. David Hwang may have had brilliant, revolutionary ideas,
but Jack Donnelly knew where pieces of the system could be best
tweaked.

A union between the two could have worked,
but Boston didn’t have a precedent for a co-mayor, and when that
was suggested by Donnelly after Hwang lost the primary by half a
percentage point, it reeked of desperation. That was...odd. To the
untrained eye, it looked as if Donnelly was trying to lose.

~~~

The rule was that if you were going to run
for mayor, you had to give up your council seat. The upshot during
that cycle was that there were now two seats to be filled, and
Paloma Castillon easily filled one of them. Before the last mayoral
race, it was as if she didn't exist; then she was everywhere, feted
by women's groups, Progressive Democrats and even the state's
Democratic Party. Her win was as impressive as David Hwang's, but
at least Martin knew whose head David had jumped out of.

Professor Marguiles sat with his arms crossed
as Martin gave his bi-weekly update on his research progress. "And
now you want to know where Castillon came from?"

"This much I know: she started school here,
then she dropped out. And it was night school. She disappears for
about six months, then she's working for a Fitzgerald. That job
lasts for a little while, then she's in Senator Kelly’s office.
Kind of a big leap in title, and then a bigger leap a few years
later."

"But?"

"But those are the kind of jobs you get after
you've been an intern for a few cycles, if you're politically
connected or if you graduated with at least a Bachelor’s. And none
of that applies. I might not be so fascinated if it weren't so hard
to figure out," Martin confessed. "I've even looked at the Chicago
papers, and I can't find anything, really, before her first
run."

"You know she didn't graduate with a degree,
and you know she wasn't an intern. How do you know she wasn't
connected?"

"She grew up in the projects of inner city
Chicago."

"Did she now?" Marguilles' beard did a lousy
job of hiding his smile. "You know who that reminds me of? The
governor."

Martin cursed himself when he looked over
Governor Kirk's file. Why hadn't he seen it before? Because, like
everyone else, when he thought of the governor, he thought about
his association with that other guy from Chicago: the President of
the United States. Martin raised an eyebrow, but quickly ruled it
out: Chicago may have been the place that molded him, but that was
after he was an adult with a law degree under his belt. And he may
have been a community organizer, but by the time he got that job
Castillon was sitting in Kelly’s office...

Martin looked through his records, just to
confirm what he already knew. There was Alex's name in the donor
lists for Castillon, Kirk and Kelly. He pulled up the lists for all
of the groups who had put Castillon's name on Boston's map. There
he was as well.

Did Castillon know that she, like almost
everyone else in Boston politics, was Alex Sheldon's creature?

He couldn't stop himself from discussing
Donnelly with Jessie. "Yeah, sounds like he wanted to go back to
law," Jessie said nonchalantly.

"Huh?"

She shrugged. "He might have had a chance at
winning if he had run a strong campaign, but he didn't reach out
beyond his power base. Not in any way that counted. What was the
only thing he could count on? That he was going to have to give up
his seat, and the only way he could do it and not have his dad to
worry about was by pretending to run for mayor."